The Pines features zigzag boardwalks that lead to the island’s most ritzy real estate. The Pines turnout is known to be a bit more subdued than its neighboring Cherry Grove. Charitable fundraisers and cocktail parties fill the Fire Island Pines’ social calendar, with the annual “Invasion of the Pines” event being perhaps the most notable.

The Pines caters to its Manhattan weekenders and features delightful markets, boutiques, and restaurants. Home of the “tea dance,” Fire Island Pines is a zigzag of boardwalks that lead to the island’s most ritzy real estate. The Pines turnout is known to be a bit more subdued than its neighboring Cherry Grove. Indeed the Pines is an affluent gay-friendly community where same-sex, as well as heterosexual lifestyles, co-exist comfortably. It is fabled that Fire Island Pines was named due to a shipwreck in which a cargo of evergreen trees that were being transported for the Christmas season came to shore and took root, giving the area its lush green appearance. While this may or may not be true, the Lone Hill Lifesaving station was located in this proximity of Fire Island during the 19th Century. The Lone Hill building was used as the Fire Island Pines Community House right through the 20th Century until it was ultimately razed and Whyte Hall took its place. In 1924 the Home Guardian Company purchased the tract of land that would become Fire Island Pines for the purposes of Real Estate development. But with the Great Depression followed by the Second World War, the tract languished until 1952 when the Smadbeck Brothers (also known as the “Henry Fords of Real Estate”) subdivided the into 122 lots for sale and constructed a private harbor with large landing dock with the vision of marketing the community to the boating enthusiast. And while this vision did, in fact, become true, dynamics of the era made the conditions right to make the area attractive to a wealthy gay clientele.

Today charitable fundraisers and cocktail parties dot the Fire Island Pines’ social calendar also summer long, with the annual “Invasion of the Pines,” the Fire Island Dance Festival and the Ascension Party being among the most notable.