The swimming area in Cunningham Park was originally established in 1922 and is affectionately referred to as “The Pond”, given its spring-fed origins. Like a natural pond, the water in this pool is partially spring fed; any supplementary water is provided by nearby wells. The pond is supported by a state-of-the-art filtration system and is a remarkable 42,000 square feet. At its deepest point, the pond is approximately 8’ deep.
This treasured park asset is named in honor of Bill Caldwell who served as Park Manager for nearly five decades until his retirement in 1957. The Pond is more than just a place to cool off; it’s where many of Milton’s children learn to swim, and where summer friends – and memories – have been made for generations.
The Caldwell Pond is available to all Milton residents and will be open for the season in 2025 from June 18th - August 19th. REGISTRATION FOR SUMMER 2O25 NOW OPEN!
REGISTER FOR MEMBERSHIPS HERE!
THE POOL WILL BE OPENING JUNE 18TH, 2025
2025 Cunningham Pond memberships available to purchase June 12th!
Memberships are only available for residents of the Town of Milton.
If you need assistance because of technology, please come to the Pond gate during operating hours and we will be happy to help you in person.
Individuals/Families
- For individuals under 65 years old and multi person households/families, register for one (1) membership through the "Cunningham Pond 2025 Family/Individual Membership" link
- Household Memberships are $150.00 for the 9 week 2025 season.
Seniors
- For individuals 65 years of age or older, register for one (1) membership through the "Cunningham Pond 2025 Individual Senior (65+) Membership."
- Senior Memberships are $50.00 FOR EACH INDIVIDUAL SENIOR IN THE HOUSEHOLD for the 9 week 2025 Sumer season.
GUEST POLICY:
- Guests must register at front gate with a member of the Pond.
- All Milton residents using the Pond should have their own membership, so guests can not be Milton Residents.
- Cost of a guest is $5.00 and good for the whole day.
- When checking in at gate guests must present a form of ID and their information will be saved so that they are able to use our facilities for the remainder of the day.
With questions, please call (617) 696-3263 or email us at pond@cunninghampark.org
Monday - Friday:
9:00 AM - 10:00 AM - Senior Swim
10:00 AM - 12:00 PM
1:00 PM - 4:00 PM
5:00 PM - 7:00 PM - Family Night Swim
Saturday & Sunday:
10:00 AM - 1:00 PM - Family Swim
2:00 PM - 5:00 PM - Family Swim
**Thursday June 19th and Friday July 4th will operate on a weekend hours schedule.
**Thursday July 3rd will be closed for night swim.
2025 SESSION 1 OFFERINGS - Each class is 2 days a week for 4 weeks. Classes are offered either Mondays and Tuesdays (M/T) or Wednesdays and Thursdays (W/Th)
AM Sessions:
*Level 1 - 10 AM Mon/Tue or 10 AM Wed/Thur
11 AM Mon/Tue or 11 AM Wed/Thur
*Level 2 - 10 AM Mon/Tue or 10 AM Wed/Thur
11 AM Mon/Tue or 11 AM Wed/Thur
*Level 3 - 10 AM Wed/Thur
11 AM Mon/Tue
11 AM Wed/Thur
*Level 4 - 10 AM Mon/Tue
PM SESSIONS
*Level 1 - 5 PM Mon/Tue or 5 PM Wed/Thur
6 PM Wed/Thur
*Level 2 - 5 PM Mon/Tue or 5 PM Wed/Thur
6 PM Mon/Tue or 6 PM Wed/Thur
*Level 3 - 5 PM Mon/Tue or 5 PM Wed/Thur
6 PM Mon/Tue or 6 PM Wed/Thur
*Level 4 - 5 PM Mon/Tue
6 PM Mon/Tue or 6 PM Wed/Thur
Cost of lessons is $40.00 (cash or check)
Your child must be 5 years of age by the first class. Birth certificates are needed for 5 and 6 year olds.
We will try to keep a 6:1 student-to-teacher ratio for each class to maximize your child's time.
Classes are 45 minutes long (approx 40 min in the water)
Levels*** Please read as our descriptions have changed. Water Safety Instructors will be on hand to help you decide where to best place your child. They will be evaluated the first week and if they need to be moved the instructor will do their best to find you a class that is similar to the one you signed up for. We always recommend playing it safe with Levels because putting your child in something they are not ready for can harm them more than help them. Our goal is for your child to know water safety and to be comfortable in the water.
Level 1 - Introduction and Fundamentals of Water Skills
Level 2 - Stroke Development
Level 3 - Stroke Improvement
Level 4 - Stroke Refinement and Skill Proficiency
SESSION 1 STARTS June 23nd. 4 weeks - June 23, June 30, July 7, July 14
Any questions please feel free to email pond@cunninghampark.org and we will get back to you as soon as possible!
We have many talented guards that are on HS swim teams looking to create a team!
Cunningham Park was established in 1904 to fulfill Mary A. Cunningham’s wish that her bequest be used “for the benefit of Milton residents.” Mary grew up in the house on Adam Street that is now the Forbes House Museum.
