Waterfront and Sailing
Pine Pond is an approximately 80 acre natural lake central to life at the Gipsy 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 Gipsy Trail Club owns and carefully manages all of the land surrounding Pine Pond.
 
Beach
The Gipsy Trail Club beach is a focal point for summer swimming, sun bathing, volleyball and cookouts. The large sand beach, 50 feet deep and over 100 feet long, is groomed daily and life guards are on duty seven days a week from Memorial Day to Labor Day. There’s also a separate shallow-water children’s beach. Lunch, snacks and beverages are available at the Snack Bar located directly on the beach.
 
Boathouse
The Gipsy Trail Club boathouse has recently been lovingly restored. This classic “Adirondack style” building provides storage for over 50 sail boats and canoes as well as changing rooms and private lockers. Sailing lessons and races are a regularly scheduled activities from June to August. Canoes and kayaks are also available for member use at any time.
 
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.
 
Sailing
Pine Pond Yacht Club, founded in 1960, offers Sunfish sailing opportunities for all members of Gipsy Trail Club. A long established racing program takes place every Saturday at 1:00 p.m. 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 for the regattas are awarded at the annual fall Flags ‘N Cups Dinner. Less formal sailing races continue after Labor Day until Columbus Day Weekend. Fun events, such as a parent/child sailing Regatta on Father’s Day Weekend, are held during the summer.
 
Group sailing lessons for introduction to sailing safety and skills are planned for early in the season. Individual instruction, provided by experienced member sailors, is available by appointment throughout the season. Club owned boats are available for use and members’ boats may be for sale from time to time.
 
Please click here for all Waterfront Safety Rules and Lifeguard Hours