Cherry Grove: Fire Island Fun for Everyone – Plus Video!

WATCH VIDEO: Scroll below to view Mike Diamond’s delightful Cherry Grove video journal. Drag divas and party boys galore!

All views on Fire Island are a little askew. That’s its charm!

Fire Island has long been known as the beachy summertime getaway for Manhattan gays. Since the early part of the 20th-Century, homo New Yorkers who like sand, sun, salty sea air and the company of other gays (and their artsy friends) have ferried it out to the car-free little slip of an island which runs parallel to the southern shore of Long Island, about 90 minutes away from the city.

The length of Fire Island is populated by a slew of little beach communities, and located just across the water from Sayville, New York you’ll find the two villages of Fire Island Pines and Cherry Grove.

To the east, Fire Island Pines is more of a male-centric community, hosting gay guys who share a fondness for splashy beach homes, socializing over drinks and dance music, and the veneer of an upwardly mobile social scene. Think gay gentry: Moguls and arty magnates (like Tommy Tune, David Geffen, Jerry Herman, Calvin Klein) have been fixtures here through the years, as have well-to-do gay businessmen and the handsome lads who fancy their company. Today, it’s a mix of young professionals and established gay men who enjoy getting their tan—and party—on!

The dunes by the beach at Cherry Grove.

To the west, just down the beach about 10 minutes—or through the twisted paths through the woodsy, storied “Meatrack” (it’s a forest between two little gay communities; use your imagination) you’ll find Cherry Grove. (Ferries from Sayville served both communities independently.) A little more low-key in scale when compared to the Pines, Cherry Grove is an enclave where the houses are smaller, the beachgoers a bit more diverse (many more lesbians and some families) and the vibe is more kitschy-meets-crunchy. The scene is relaxed, rollicking and welcoming to anybody.

A typical street view in Cherry Grove. No cars, just boardwalks.

The Cherry Grove crowd veers toward a mix of old salty regulars, young artsy/hipster types from Brooklyn and Manhattan, and down-to-earth working folks. Expect to find your butch high-school gym teacher from Long Island, and her fun-loving life partner, Debbie.

Cherry Grove also has a fun smattering of bars (featuring drag shows, pool parties, weekly underwear parties, show-tune nights), a few shops, and a sprinkling of little eateries and restaurants that veer toward cute seafood shacks or casual cafes, as well as a pizza parlor and an ice cream shop.

And so it’s to Cherry Grove that we sent Mike Diamond, with a cameraman in tow, to just sniff out a small sample of the sassy summer flavor that the Grove has to offer. Check out his twisted video visit! Granted, his take is his own, caustic and dishy. But you’ll get a sample of the Grove’s fun flair.

And below, get a quick list of some of our picks of the best of what Cherry Grove has to offer.

VIDEO: Mike Diamond Takes on Cherry Grove!



The Grove Hotel
Part of a big complex that towers over the central part of the Cherry Grove village, the Grove Hotel is the hub of the social scene in Cherry Grove. Rooms may be small (but sizes do vary), but if you want to stay in the thick of things where you have a busy pool and thumping bar/nightclub on site, this is where you want to be.

Chillin’ in the pool at the Grove Hotel.

Dune Point
Dune Point rents little apartment/cabana-type lodgings just steps from the beach. Check into a 2-bedroom rental with friends, or go solo (or with your very significant other) in a studio or one-bedroom. Some have AC, most have private baths—there’s a good mix of sizes and styles. Some have ocean views!

Get ready for the Belvedere…

Welcome, Gentlemen…

Belvedere Guest House for Men
A big rollicking, vast and ornate Venetian Palace (really!) the Belvedere is a landmark and a legend. The vibe is very Tennessee Williams meets Shangri-La! Cupolas, painted frescos, decks and verandas, ornate décor everywhere… The clientele veers toward gay gentleman 35 and over who travel from all over to chill by the clothing-optional pool and lounge on its many decks and balconies. The scene is decadent and boasts its own storied (and sometimes seedy) charm. It’s major.


Logan Hardcore gets wet and wild in her Saturday afternoon show by the Ice Palace pool.

Ice Palace
The Ice Palace is the big bawdy grand dame of the Cherry Grove nightlife scene. Perched in the center of town, the spacious bar and club hosts nightly shows and parties, and boasts a fab and starry roster of drag talent, veering from classic kitsch to cool downtown NYC divas. Come the weekend, the daytime scene by the pool is fabulous and fun, with poolside shows from divas like Logan Hardcore, Dallas Dubois and Ariel Sinclair.

Cherry’s on the Bay

A gorgeously situated and fun bar and café perched on the bay with stunning sunset views, Cherry’s is always a rollicking good time. You’ll love the big sprawling Cherry “tree” of branches and sparkly lights that looms over the entire central bar area. And there’s a dancefloor and shows by major NYC drag talent like Sweetie, Gusty Winds, Epiphany and more!


Cherry Lane Café & Restaurant
The Cherry Lane Café is a reliable spot for morning coffee, breakfast, lunch and dinner. Serving simple beach café fare, you can dine on the front porch at the Cherry Lane Cafe and watch the daily traffic pass by, or sit out back on the upstairs deck with a full view of the gorgeous Fire Island bay.

Jumping Jack’s Seafood Shack
Perched with great views right on the dunes, Jumping Jack’s gives you the perfect beachy vibe. The food’s not fancy, but go for shrimp, mussels, fresh clams and fish, good pasta dishes and fun cocktails. But really go to just sit out on the dock and chill in the ocean breeze. The crowd is casual and fun. A Fire Island classic.

Cherry Grove Pizza
Staffed by sassy Long Island girls and flirty young gay boys (and some straight lads, too) this joint serves up yummy slices, pies and Italian subs and grub on wooden patios tucked just under the Ice Palace. Cheesy goodness.

The breakfast and lunch spot smack in the middle of town. A bit overpriced, but it’s all tasty, well-prepared and very friendly. You’ll see everyone (including last night’s hookup) sauntering by on their way to the dock or the grocery. Social and sassy—and they love dogs!

Walking into the main village area of Cherry Grove…

Island Breeze
An attractive breezy spot right by the ferry dock with great views of the bay, the Island Breeze serves up tasty cocktails and reliable lunch and dinner fare. Daily specials.

Top of the Bay Bistro
Perched overlooking the dock with killer views of the bay, Top of the Bay serves up a popular Sunday brunch and pleasant upscale bistro fare.

Sweet Licks: Ice cream to scream about.

Sweet Licks
Cute little ice cream parlor tucked just under the front deck of the Ice Palace.

No cars are permitted on Fire Island, so to get to Cherry Grove, it’s easiest to take the Long Island Railroad from NYC’s Penn Station to Sayville. Upon arrival in Sayville (generally from May through September) there will be shuttle bus services offering $5 rides for the 7-8 minute jaunt to the Sayville Ferry. The ferry ride is $14 for a round-trip. Click for the full seasonal Fire Island ferry schedule for both Cherry Grove and Fire Island Pines.

The classic sunset view over the bay from Cherry Grove.

John Polly is a former editor at NewNowNext. He now makes the magic happen at World of Wonder.