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Dotted along the shore are Fire Island towns with character all their own, from LGBTQ+ utopias and sizzling nightlife to family-focused and easy-going.
Here are some of the most visited to check out on your next trip!
Cherry Grove
Considered America’s first gay and lesbian town, Cherry Grove is an LGBTQ+ haven where people can be themselves. It’s known for meandering, tree-shaded boardwalks, electrifying nightlife, waterfront restaurants and cocktail bars, unique shops, and events like the Miss Fire Island contest.
Landmarks include the palatial Belvedere Guest House, Ice Palace 23 nightclub, and the town's lifeblood, the Cherry Grove Community Center and Theater, which is listed on the National List of Historic Places and still going strong.
The Pines
Connected to Cherry Grove by a short walk through Judy Garland Memorial Pathway, Fire Island’s “Pines” is another LGBTQ+ utopia with zig-zagging trails canopied with lush foliage, a pristine beach, markets, boutiques, and restaurants.
With marvelous mid-century modern architecture, it has the most expensive real estate on Fire Island and the most pools.
The packed social calendar features the signature “tea” dance parties, evolved from when same-sex couples couldn’t legally dance together. “Invasion of the Pines” is an annual event where drag queens arrive to the town via ferry to celebrate its history and legacy.
Ocean Beach
Ocean Beach is the unofficial capital of Fire Island. It is the largest village on Fire Island, once graced by fashionistas and theater greats such as Marilyn Monroe and the Gershwins. Homeowners and young families mix with the day-trippers who come for the beach and bar dancing. You'll find plenty of shops, restaurants, art galleries, and entertainment.
Cleanliness and safety are paramount. Eating on the beach is not allowed to prevent litter.
For sunset dining, head to The Hideaway for its eclectic dinners or Housers Bayfront Bar and Grill for a “Zippy Cooler” and the lobster special.
Kismet
Charming and mellow, Kismet on Fire Island is popular with families, singles, group house renters, and day-trippers and is less crowded than many other communities.
In addition to its gorgeous beach with a playground, it has a bustling 100-slip marina, and you can walk to Robert Moses State Park and the Fire Island Lighthouse. A smattering of restaurants and stores serve the Margaritaville atmosphere.
Unlike most Fire Island communities, you don’t need a ferry to get here.
Ocean Bay Park
Once planned as a retirement community for New York police and firefighters, Ocean Bay Park turned out to be an eclectic mix of artists, professionals, families, and—yes—retirees.
They hang out happily with the day-tripping partiers at popular town watering holes with live music and restaurants, such as Canes at the FIBH.
Modern, experimental beach houses that look like ships and kites sit alongside traditional bungalows, adding to the quirky feel.
Fair Harbor
Centered around a picturesque harbor, it’s rare to see someone wearing shoes, yet the Fair Harbor on Fire Island hums with activity. The beaches, kept immaculately clean for those bare feet, are patrolled by lifeguards.
Residents and visitors enjoy fine dining, a favorite ice cream shop, and parties when not on the beach.
The Pine Walk Crafts Fair on Fourth of July weekend is a signature annual event.
No matter how you’d like to spend your vacation on beautiful Fire Island, there’s a community that fits. Choose the ferry that takes you to that shore!
