The more than one thousand acres that now comprise the Gipsy Trail Club was once home to the Wappinger Indians (known as "Gipsies" by the locals), a division of the Mohican tribe until they sold the land in 1691 to a pair of Dutchmen, Dorland and Seabrant. The Club lies in the shadow of Mt. Ninham, named for the last living chief of the Wappingers, who died supporting Washington’s troops in the revolutionary war.
In 1910 a group of New York fishermen employed a realty concern to begin acquiring all the land surrounding Pine Pond. By 1911, the 10 parcels were conveyed to the Kentwold Company. Little improvements were made to the property and, after the death of two of the incorporators, in 1923 the land was leased to two New York real estate men, Culver and Whittlesey, with an option to purchase. At the same time a promoter named Carl Anderson was seeking a tract of land with a lake within 60 miles of New York City that would be suitable for development into a community such as Gipsy Trail Club. On July 24, 1924, Anderson and Miner D. Randall purchased all of the stock from Whittlesey (Culver had since passed away) and formed the Gipsy Trail Holding Corporation with the option to purchase the property before March 1st, 1926.
Gipsy Trail Camp and Country Club was incorporated with the State of New York on July 25th, 1924 with Carl Anderson as general manager and controlling stock holder. Until November of 1926, the Club was wholly controlled by Anderson and his associate, at which time a board of 18 members was established to quiet growing dissatisfaction. In February 1927 Anderson sold controlling stock interests to 54 members and in March of 1928 the ownership of the Club was completely transferred to the membership. The by-laws of the new Gipsy Trail Club, Inc. were issued in the summer of 1929.
Seventy-five lots were defined and originally leased to the members on an annual basis with one tract set aside to accommodate 14 tents for those looking for outdoor life in its simplest form. In 1934, with a fiscal reorganization of the Club, members were allowed to purchase and own their cabin sites. There are now 84 cabins owned by resident members.
The original clubhouse and lower lodge were built between 1925 and 1928 from hewn logs cut on the property and hauled across the frozen lake by teams of horses. In 1930 the upper lodge was built to provide accommodations for up to 48 people. At the same time the stables were erected to accommodate up to 15 horses.
The Gipsy Trail Club and its ethos have survived the Second World War, recessions and a fire that destroyed the original Clubhouse. The Clubhouse was rebuilt and, in 2008-2009 it was completely remodeled as a state-of-the-art facility. It remains the center of social life at the Club serving the finest of food and drinks while hosting traditional and holiday events.
The Gipsy Name
The last of the Wappinger Indians who made camps around Indian Brook Pond were referred to by locals as Gipsies. The road, now known as Gipsy Trail Road, was probably named for the Club in the 1940’s because prior to that it was known as Farmer’s Mills Road. The spelling of Gipsy is after the English spelling and derived from the early word “egipcien” which was based on the belief that the Gipsies (now Romany) had come from Egypt. Putnam County finally agreed to match the Club’s spelling of the name of the road in 1997.