DeFilippo Playground

Pickleball at DeFilippo Playground in Boston, MA runs on community energy — the courts are free to play, and locals are known to bring portable nets and welcome fellow players to join in. The playground is open every day from 6:00 AM to 11:30 PM, making it accessible for early-morning and evening sessions alike. Players note that court markings can be limited, so arriving when regulars are already set up is the best approach. Rated 4.5 out of 5 across 70 reviews, the multi-sport site is in good condition and sits within a well-rounded community park that also includes a dog park, picnic area, and water access.