About Us
Gipsy Trail Club* is a private membership community founded in 1924. It is located on 1000 pristine acres of wooded lands a little more than one hour north of New York City. The sense of community is strong. While the members join together in a variety of activities, including tennis, sailing, horseback riding, hiking, and trap shooting, the Dining Room (or Clubhouse), which is open every weekend throughout the year, provides the setting for conversation and friendship. In the summer, the most important activity on any given day may involve nothing more than time spent on the beach. Since its inception, the Club has attracted a membership that is active and actively involved in creating an uncommon sense of camaraderie.
Although fully staffed, the non-profit club is an organization preserved by the membership that has worked to support a legacy that has now passed through many generations. The membership reserves a deep respect for the forebears who had the vision to create an isolated and protected setting with such close proximity to New York City.
The Club maintains its own state certified community water system supplying over 84 residences and community facilities with over 10,000 gallons of fresh water daily. A full time maintenance staff provides the upkeep for a dozen community buildings along with the maintenance and plowing of over three miles of private roads and drives. While membership has risen, fallen and risen again, the Club’s philosophy of friends and families  connecting with the natural beauty that is Gipsy Trail Club remains unwavering. The Club is the strongest it has ever been with over 130 members and is in a secure financial position.
As members of the Gipsy Trail Club we are dedicated to the enjoyment of the natural world and the stewardship of the natural areas and habitats that we have agreed to protect and preserve.
* In 2021 our community voted to change our name from "The Gipsy Trail Club" to "The Trail Club".
Our new name underscores our connection to nature. These changes will take effect in 2022.