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!
Memberships are only available for residents of the Town of Milton. Your ID with proof of residency will be asked each time you enter the gate.
If you need assistance because of technology or want to pay via Cash or Check, please come to the Pond gate during operating hours and we will be happy to help you in person.
Individuals/Families
For individuals under 62 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.
If both members in the household are 65 years of age or older, you can register for one (1) Senior Couple (both 65+) Membership which cost $90.
Pre-Seniors
If you are between the ages of 62-64 you can register for one (1) Pre Senior Individual Membership which cost $75.
If you are a couple and both are between the ages of 62-64 you are eligible to register for our Pre Senior Couple Membership which cost $125
Fire or Police Membership
If you work for Milton Police or Fire you can register for the Milton Police and Fire Membership. You will have to upload verification documentation that will have to be approved before you can buy the membership
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 cannot be Milton Residents.
- Cost of a guest is $5.00 and good for the whole day.
- When checking in at gate guest 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.
Additionally, if you have a nanny or babysitter that will be brining your family members to the pool you can purchase a Nanny Membership that can be bought at the Gate. It is $10 per Nanny Membership (one person per nanny membership)
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
**During Senior Session we are now offering water aerobics on Tuesday and Thursdays starting at 9:10
In addition to having the signups at the hall on Monday July 14th we are now offering signups online at https://cunninghampond.activityreg.com/ starting at 6PM. Click Activities on the left side bar and you will be able to see all available classes for session 2. Please make sure to add your Child to your account before signing up for the class.
2025 SESSION 2 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). Session 2 Lessons start on July 21st and will go to August 15th (4 weeks).
AM SESSIONS
Level 1 - 10 AM Mon/Tue or 10 AM Wed/Thur
or 11 AM Wed/Thur
Level 2 - 10 AM Mon/Tue or 10 AM Wed/Thur
11 AM Mon/Tue
Level 3 - 10 AM Wed/Thur
10 AM Mon/Tue
11 AM Wed/Thur
Level 4 - 11 AM Mon/Tue or 11 AM Wed/Thur
PM SESSIONS
Level 1 - 5 PM Mon/Tue or 5 PM Wed/Thur
6 PM Mon/Tue or 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 Wed/Thur
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 2 STARTS July 21st. 4 weeks - July 21, 28, Aug 4, 11th
Any questions please feel free to email pond@cunninghampark.org and we will get back to you as soon as possible!
https://cunninghampond.activityreg.com/
This will be organized by some of our Head Lifeguards that are on High School swim teams or local swim teams. The team will meet every Monday, Wednesday and Friday, starting after the 16th. The cost is $40 for the 4 weeks. This will be a recreational team which will strive to have 12 sessions. Practices will run for approximately 40 min, on Monday, Wednesday and Friday evenings from 4:10-4:40pm. All new swimmers must be evaluated before joining and demonstrate their ability to safely swim 25 yards of the pool unassisted. Swimmers may join in any session they choose. You do not have to participate in all sessions. You may jump in an out of the sessions as you choose. This group will focus on providing instruction of the four competitive strokes, starts and turns and swim etiquette in order to develop the skills necessary to become a competitive swimmer (turns may be lesser practiced). It will also allow swimmers to build skills in order to participate in our other Competitive groups offered. Although we will focus on developing skills, this group was put in place to provide some healthy exercise in a fun manner. We will not require competition but will try to offer some opportunities. To secure your spot, Email us at pond@cunninghampark.org!
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.
