Shelter Island Heights was listed on both the United States Register and the New York State Register of Historic Places in 1993 “in recognition of its significance in American history and culture.” Designed about 1872 and essentially unchanged since then, the Heights is a beautiful example of the picturesque, naturalistic landscape and romantic rural residential areas created by the first generation of American landscape architects. Among these were Frederick Law Olmsted, the designer of New York City’s Central Park, and Robert Morris Copeland, who laid out the original plan for the Heights, prepared for a Methodist affiliated organization from Brooklyn. The Heights is among the few preserved communities that combined facilities for religious camp meetings with summer resort living close to New York and Connecticut.

The visual and social center of Copeland’s plan was Union Chapel (built 1875 and placed on the national register in 1984), the oldest public building on Shelter Island. It is set in a natural amphitheater, the Grove, which was also the site for an open-air preacher’s stand and tents that accommodated the people who attended the first camp meetings. But from the beginning the Heights was conceived as a community with parks, open spaces, a hotel, and lots for private residences. Between 1872 and 1880 about 70 cottages were constructed; by the late 1880s another 30 were added; by 1890 the current layout was defined.

Today the Heights Historic District consists of 141 buildings, designed in several distinct styles. The original cottages built in the first decade are in the exuberant folk architecture found in camp meeting sites such as Oak Bluffs on Martha’s Vineyard and Ocean Grove in New Jersey. The most striking feature of these steeply pitched gable roof structure is the elaborate and delicate wood trimming on verandas, gables, windows, and doors.