As Fire Island’s oldest community, Point O’ Woods is self-contained and offers a clubhouse, tennis courts, park, and market to homeowners. Point O’ Woods insular nature is exemplified by its massive fence that encloses the community. POW residents are preppies that treasure their private community and do their best to discourage visitors from passing through. This rustic neighborhood has a strong emphasis on family living and the look and feel of a bygone era burrowed in wooded terrain sit a collection of old houses and ancient bicycles.

Point O’ Woods has its roots as a Chautauqua retreat in 1894. While this forum for spiritual and self-enlightenment was a very popular concept at the time, the enterprise was a financial failure and dissolved within four years. Unsuccessful as the Chautauqua enterprise may have been, it gave birth to the organization of the first true residential community on Fire Island. Point O’ Woods operated on the premise of 99-year leases of the land which is held in common by the Point O’ Woods Association, while the houses themselves are privately owned. This has kept the appearance of Point O’ Woods relatively unspoiled by progress. Point O’ Woods also has an unusual demographic for Fire Island. Well-pedigreed families come from all corners of the country to summer at Point O’Woods, while many neighboring Fire Island communities are predominantly populated by New York City and greater Long Island summer residents. Point O’ Woods residents cherish their land and water sports almost as much as they value family, continuity in their way of life, and of course their privacy.

Like many of the western Fire Island communities, ferry service is out of Bay Shore, NY.

In fact Point O’ Woods pioneered Bay Shore as a launching spot for ferry service to Fire Island. Before that most ferry service to Fire Island originated out of Babylon, NY. Today the Point O’ Woods ferry line is the last remaining ferry line in Bay Shore that has not been absorbed by the conglomerate, Fire Island Ferries Inc.