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Pine Pond is an approximately 80-acre natural lake central to life at the Trail Club. Fed by the East and West brooks and natural springs, water from Pine Pond flows into the West Branch Reservoir of the Croton water system. The Trail Club owns and carefully manages all of the land surrounding Pine Pond.

The Trail Club beach is a focal point for summer swimming, sunbathing, volleyball, and cookouts. The large sandy beach is groomed daily, and lifeguards are on duty seven days a week from Memorial Day to Labor Day. Lunch, snacks, and beverages are available during weekends at the Snack Bar located directly on the beach.

The Trail Club boathouse, a classic “Adirondack style” building located at the waterfront, provides storage for over 50 sail boats, canoes and paddleboards, and changing rooms and private lockers. Sunfish boats, canoes, paddleboards and kayaks are also available for member use without charge.
The Commodore’s Club, located on the second floor of the boathouse, offers a breathtaking vantage point of Pine Pond from its balcony porch. The space features a large stone fireplace for warm winter gatherings.



Pine Pond Yacht Club, founded in 1960, offers Sunfish sailing opportunities for all members of the Trail Club. A long-established racing program takes place every Saturday from Memorial Day Weekend through Labor Day, with regattas consisting of races on a series of weekend days. Scores are recorded for each race, and trophies for the season and the regattas are awarded at the annual fall Flags ‘N Cups Dinner. Fun events, such as a parent/child sailing regatta on Father’s Day Weekend and Capture the Flag, are held during the summer.
Group sailing lessons for introduction to sailing safety and skills are planned for early in the season, and group instruction for children may also be arranged. Individual instruction, provided by experienced member sailors, is available by appointment throughout the season, and group instruction for children may also be arranged. Club-owned boats are available for use by members without charge, and members’ boats may be for sale from time to time.