Briarcliff Manor spring festival centers on pickleball, family fun at Chilmark Park

Chilmark Park is about to become Briarcliff Manor’s spring festival hub, with pickleball at the center rather than parked on the side. Picks and Pickleball will bring a friendly tournament, open play for kids and adults, live music, food trucks and family programming to the village’s six-court park at 48 Macy Road.

The village notice set the event for Saturday, May 9, from 11 a.m. to 4 p.m., with a rain date of May 16. Official festival materials listed a broader 12 p.m. to 5 p.m. spring festival window at Chilmark Park, with a May 17 rain date. However the clock shakes out, the setup is clear: this is being built as a court day wrapped in a community party.

Cross Court Pickleball Hawthorne will run the friendly tournament, and tournament spots require paid registration. Macaroni KID Northern Westchester says the bracket is open to players at the 3.5 to 4.0+ skill levels and that registration is already filling fast. For players used to plain rec play, that matters. It turns a village park date into something more structured, with enough demand to justify advance sign-up and skill separation.

The rest of the festival is designed to keep families on site. The lineup includes School of Rock Briarcliff Manor, lawn games, a Kids’ Zone, crafts, sensory play and bubbles for the kids, along with cold beer from Captain Lawrence, food trucks and friendly goats. Presented by the Village of Briarcliff Manor, River Towns Music Group and Macaroni KID Northern Westchester, it is less a one-note pickleball event than a full park takeover with pickleball as the draw.

That model fits Chilmark Park unusually well. The 8.3-acre site was purchased by the village after years of service as the Chilmark Country Club, and the recreation department says its six pickleball courts are available to permit holders from 9 a.m. to dusk daily. A 2025 village notice described Picks & Pickleball as the event’s third year, which suggests Briarcliff Manor has already found something more durable than a one-off community notice: a repeatable way to use pickleball to pull in players, parents and neighbors on the same afternoon.