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Thursday September 18, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Friday September 19, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
4:15 PM - 5:00 PM    Gatta Pickleball Match
 
5:00 PM - 9:00 PM    Friends of Winthrop Beach - Jaws Movie night
 
6:00 PM - 8:30 PM    Middle School Open Gym
 
Saturday September 20, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 9:00 AM    Loomis pickleball match
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
11:00 AM - 12:00 PM    Conley Pickleball batch
 
5:00 PM - 6:00 PM    Loomis pickleball matc
 
6:00 PM - 7:00 PM    Loomis pickleball match
 
Sunday September 21, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
9:00 AM - 11:00 AM    Soccer Shots
 
5:00 PM - 6:00 PM    Fechtor Pickleball match
 
Monday September 22, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
5:30 PM - 6:30 PM    Decarlo Pickleball match
 
Tuesday September 23, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
1:00 PM - 2:00 PM    Fechtor Pickleball match
 
6:30 PM - 7:30 PM    Marsden Pickleball match
 
Wednesday September 24, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
5:30 PM - 6:00 PM    Ross pickleball Finish match from Wed Sept 17
 
7:00 PM - 9:00 PM    Spinazzola basketball
 
Thursday September 25, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Friday September 26, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
6:00 PM - 8:30 PM    Middle School Open Gym
 
Saturday September 27, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
12:00 PM - 2:00 PM    Birthday Sara Soper-Stevens
 
Sunday September 28, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
9:00 AM - 11:00 AM    Soccer Shots
 
Monday September 29, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Tuesday September 30, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Wednesday October 1, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
7:00 PM - 9:00 PM    Spinazzola basketball
 
Thursday October 2, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Friday October 3, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
6:00 PM - 8:30 PM    Middle School Open Gym
 
Saturday October 4, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Sunday October 5, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
9:00 AM - 11:00 AM    Soccer Shots
 
1:00 PM - 4:00 PM    Birthday party Bianchino
 
Monday October 6, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Tuesday October 7, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Wednesday October 8, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Thursday October 9, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Friday October 10, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Saturday October 11, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
11:00 AM - 3:00 PM    FALL Fair and Craft Show - Fall Fair and Craft Show Vendor Space 2025
  FALL FAIR AND CRAFT SHOW AT INGLESIDE Park is scheduled for Saturday,  October 11th, 2025 FROM 11 AM - 3PM. RAINDATE: Sunday, Oct 12th, 2025 11AM - 3PM.Pumpkin Painting, Amusements, Pony Rides,Train Ride, Moon Bounce, Games, Food, Entertainment. Craft Tables Spaces Available (tables not supplied)Vendor space is available. Register online at www.winthroprec.com  $25.00 per table (must provide own table) Register online with a credit card  or download the form on the site  and return to the parks and recreation office with a cash or check (made payable to the Town of Winthrop).  If mailing check, address is 151 Pauline St. Winthrop, MA 02152.
 
Sunday October 12, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
9:00 AM - 11:00 AM    Soccer Shots
 
Monday October 13, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
8:00 AM - 8:00 PM    WINTHROP FALL PICKLEBALL LEAGUE - Winthrop Fall Pickleball League
WINTHROP FALL PICKLEBALL LEAGUEJoin Our Exciting New Pickleball FALL Tournament League – All Levels Welcome! SEPTEMBER 8TH - OCTOBER 13TH$40 PER TEAMIngleside Park________________________________________________________________________________________We are thrilled to invite you to join our upcoming Winthrop Pickleball Tournament League! Whether you’re a seasoned player or just starting, this is a fantastic opportunity to enjoy the game, improve your skills, and meet new friends in our vibrant community. ________________________________________________________________________________________HOW DO I SIGN UP?You must read and review all information in the below attached PDF under forms before signing up. Each team must have at least two players (with at least one player being a Winthrop Resident)  Upon registration and payment below please email parksandrecreation@winthropma.gov the attached form with your teams information. Each team cost $40 dollars and each individual may only participant on 1 team.________________________________________________________Each team (with at least one Winthrop Resident) must obtain a Winthrop Parks and Recreation Tennis/Pickleball key to gain access to the courtsKeys can be purchased online or at the Recreation office for a fee of $15 Please contact the Winthrop Recreation Department by telephone or email with any questions!
 
Tuesday October 14, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
Wednesday October 15, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
Thursday October 16, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
Friday October 17, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
Saturday October 18, 2025
6:00 AM - 11:59 PM    TENNIS/PICKLE BALL COURT KEY - Tennis/ Pickleball Court Key for Ingleside Park and High School Courts
TENNIS/PICKLEBALL COURT KEYS FOR INGLESIDE PARK COURTS and HIGH SCHOOL COURTS ON MAIN STREETPickleball courts located at Ingleside ParkKEYS ARE FOR WINTHROP RESIDENTS!Quickest way to obtain key is to purchase online now and then come by the office to pick it up!Proof of residency is required. Court keys are required  to enter into the Ingleside Park and High School Courts. This policy has been designed to keep the bike riders, skate boarders, roller bladders, dogs, etc. out of the tennis area as well as non residents not accompanied by a Winthrop resident with a key.Tennis keys can be purchased Monday - Friday between 10:0am to 5:30pm at the Winthrop Recreation office located in the rear of 151 Pauline St. (the old middle school/ high school -enter driveway off of Brookfield Rd).If you cannot make these hours please call the office at 617 846-8243 to make other arrangements.The cost of the key is $15.00.
 
2:00 PM - 5:00 PM    Birthday party tranfaglia