Part of the Gay Fire Island Guide — bars, events & things to do.
Thursday, June 11, 2026
Cherry Grove & The Pines, Fire Island
Fire Island, NY 11782Let people know you're going, see who else is attending, and share the event with friends.
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Cherry Grove is where gay America summered before there was a word for it. Here's the complete guide to Fire Island's original queer hamlet — its history, its drag-soaked nightlife, where to stay and eat, the beach, and how it differs from the Pines next door.
Robbie S.The Fire Island Pines is the glamorous, modernist, party heart of gay Fire Island. Here's the complete guide — its architecture and history, the tea-dance nightlife, where to stay and eat, the beach, and the marquee events, plus how it differs from Cherry Grove.
Robbie S.Dining on Fire Island is casual, harbor-side, and woven into the rhythm of the day. Here's where to eat across Cherry Grove and the Pines — the sit-down dinners, the coffee-and-provisions spots, the late-night slice, plus how to provision a share house.
Robbie S.
The ultimate LGBTQ+ guide to Fire Island — Cherry Grove, The Pines, nightlife, legendary events, beaches, and where to stay on America's original gay paradise.
Robbie S.For one long weekend every June, the two gay hamlets of Fire Island trade their usual glossy, gym-cut summer crowd for a furrier one. Fire Island Bear Weekend brings hundreds of bears, cubs, otters and their admirers to Cherry Grove and the Pines for five days of pool parties, tea dances, a bear contest, drag brunches and late-night dancefloors — all set on a car-free barrier island where the only way in is a ferry and the beach is always a two-minute boardwalk away.
It's one of the friendliest weekends on the Fire Island calendar: less about who's on the guest list and more about a big, welcoming pack of guys taking over the boardwalks. Here's everything you need to plan it — the full 2026 lineup, where to stay in each hamlet, how to actually get there, and what a first-timer should know.
Here's the shape of the weekend at a glance:
Pro Tip
Fire Island Bear Weekend lands in early June, at the very start of the island's summer season — before the Fourth of July crowds and Pines Party push prices to their peak. That makes it one of the better-value big weekends to book, but ferries and the handful of guesthouses still fill fast. Lock lodging and your weekend pass well ahead.
Fire Island Bear Weekend is a five-day bear takeover of Cherry Grove and the Pines — the gay world's version of a summer-camp reunion, if summer camp had a clothing-optional tea dance. "Bear" is shorthand for a whole community: bigger, hairier, huskier gay and queer men and the cubs, otters, wolves and chasers who love them. A bear weekend is built around that crowd — the parties skew come-as-you-are, the dress code is often just a jockstrap and sunscreen, and the whole thing runs on an easy, affectionate energy.
What makes the Fire Island edition special is the setting. Most bear weekends happen in a single hotel or resort; this one uses the entire island. Parties hop between Cherry Grove — the older, campier, more bohemian hamlet — and Fire Island Pines, the glossier community next door, with the wooded stretch known as the Meat Rack in between. Over one weekend you'll ride the ferry, walk the boardwalks, hit the beach, and bounce between both communities' bars. It's a proper island weekend, not a hotel lobby.
See What's On Across Fire Island This Summer
Browse live events and venues across Cherry Grove and the Pines — tea dances, drag, parties and more — on the Out x Out app.
The Urban Bear builds the weekend around a rotating set of signature parties across both hamlets. Here's how June 11–15, 2026 unfolds — buy an all-access pass or pick off individual events:
Pro Tip
The two can't-miss anchors are the **Fire Island Bear Contest** on Saturday afternoon and the **Mega Pool Party** on Sunday. If you only come for a day, come Saturday for the contest-into-Truck Stop run, or Sunday for the pool party. Exact set times and DJs firm up closer to the weekend — check the official Eventbrite before you build your day.
Fire Island Bear Weekend isn't a new invention — it's an established June tradition that has been running for well over a decade. It was founded by veteran NYC nightlife promoter Shane Tate, who grew it from a small gathering into one of the East Coast's marquee bear weekends; the event marked its 10th anniversary in 2025.
That same year, The Urban Bear — the New York bear-party team led by Robert Valin, best known for the fall's Urban Bear NYC weekend — took over producing the weekend, carrying the tradition forward and expanding the lineup across both hamlets. The two events are now siblings: the same crew, one on Fire Island in June and one in Manhattan in September, bookending the bear-community summer.
Pro Tip
If you love this weekend, its sister event [Urban Bear NYC](/event/urban-bear-nyc) runs in September in Manhattan's Meatpacking District and Chelsea — same producers, city-weekend format. Doing both is a popular East Coast bear double-header.
Bear Weekend takes over venues in both hamlets, but the same handful of bars anchor Fire Island nightlife all season. In the Pines, the Pavilion is the main dance club (and the home of Truck Stop and Showtunes Sunday), with the Blue Whale on the harbor for daytime tea and drag brunch. In Cherry Grove, Cherry's on the Bay is the waterfront hub that hosts the opening party and the Bear Contest, the Ice Palace is the Grove's historic dancefloor, and Sip·n·Twirl keeps the Pines dancing well past midnight.
Fire Island, New York
Fire Island, New York
Fire Island, New York
Fire Island, New York
Fire Island, New York
Fire Island has no big hotels — you stay in a handful of guesthouses or a shared summer house, and on a marquee weekend both go fast. You're choosing between the two hamlets, and either works for Bear Weekend since the ferries and water taxis run between them.
Stay in Cherry Grove to be in the thick of the Bear Weekend daytime energy — the Belvedere and Cherry's anchor the Grove, and the community is walkable, campy and social. The historic Belvedere Guest House for Men is the Grove's grand old men-only guesthouse and a host venue for the weekend's Bear Ass Tea.
Stay in Fire Island Pines to wake up near the Pavilion, the harbor and the Sunday pool party. The Madison Fire Island Pines and The Grove Hotel are the marquee harbor-area stays.
HotelFire Island, New York
HotelFire Island, New York
HotelFire Island, New York
Pro Tip
If the guesthouses are booked, a **share house** is the classic Fire Island move: split a rental with friends and you get a deck, a kitchen and a home base for the weekend. Post in the Bear Weekend and Fire Island housing groups early — the good shares are spoken for months out. See our [where to stay on Fire Island guide](/blog/lgbtq-friendly-hotels-fire-island) for the full rundown.
Fire Island has no cars and no bridge — you get there by ferry, and for Cherry Grove and the Pines the gateway is Sayville on Long Island's south shore.
Pro Tip
Everything on the island moves by boardwalk, wagon or water taxi — there are no cars and no roads. Pack light in a soft bag you can pull in a little red wagon (the island's unofficial vehicle), wear shoes you can walk sandy boardwalks in, and bring cash for water taxis and the smaller bars.
You won't go hungry between parties. In the Pines, the Canteen is the harbor-side all-day spot for coffee, sandwiches and provisions, Pines Bistro does a proper sit-down dinner overlooking the marina, and Pines Pizza handles the late-night slice. Over in Cherry Grove, Cherry's on the Bay doubles as a waterfront restaurant when it isn't hosting a party. Because groceries are pricey and limited on the island, a lot of house-share crews bring provisions over on the ferry and cook in — but the harbor restaurants are part of the ritual, especially a sunset dinner between the afternoon and late-night parties.
Even on a party weekend, Fire Island is worth exploring in daylight — it's one of the most storied queer places in America. Cherry Grove has been a gay haven since the 1930s and '40s, decades before Stonewall, and its Community House & Theater is often called the oldest continuously operating gay theater in the country. Fire Island Pines is famous for its modernist beach houses, cantilevered over the dunes on stilts, and for inventing the tea-dance-into-night rhythm that gay resorts everywhere copied.
Between the two hamlets sits the Meat Rack (officially the Carrington Tract, though it's better known as the Judy Garland Memorial Park), the wooded stretch of the National Seashore that's been a legendary cruising ground for generations. And a short water-taxi ride west at Sailors Haven is the Sunken Forest — a rare, 300-year-old maritime holly forest below sea level, laced with a boardwalk trail, protected as part of the Fire Island National Seashore. The beach itself is the whole point: wide, clean Atlantic sand a two-minute walk from any party, best right after the pool empties out.
Pro Tip
Block out one slow morning. The Fire Island crowd treats the beach and a walk to the Sunken Forest as the antidote to a big party night — sun, salt water and a nap on the sand before the afternoon tea dance is the real Fire Island rhythm.
Fire Island Bear Weekend 2026 runs Thursday, June 11 through Monday, June 15, 2026. The main weekend is Thursday–Sunday, with a Monday-night send-off show; the event happens in early June every year at the start of the island's summer season.
It's split across Fire Island's two gay hamlets — Cherry Grove and Fire Island Pines — with parties in both. Opening night and the Bear Contest are at Cherry's on the Bay in the Grove; the big Saturday and Sunday dancefloors and the pool party are on the Pines side. Water taxis and the boardwalk connect the two.
Tickets are sold through Eventbrite. You can buy an all-access weekend pass or individual event tickets — roughly $10 to $75 per party depending on the event — plus VIP options with added perks. Some smaller events are included with the pass. Prices and the full schedule go up on the official Eventbrite ahead of the weekend.
Not at all. Bear Weekend is one of the most welcoming crowds in the gay world — bears, cubs, otters, wolves, chasers, admirers and friends of all shapes are the whole point. Come as you are; the only real dress code is sunscreen and a good attitude.
Yes. Because the Sayville ferry runs frequently and the ride is short, plenty of people come out just for the Saturday Bear Contest or the Sunday Mega Pool Party and catch an evening boat back. Confirm the last ferry to Sayville before you commit to a day trip — the late boats fill up on a big weekend.
Stay in a Cherry Grove or Pines guesthouse if you can get one — the Belvedere in the Grove and the Madison or Grove Hotel in the Pines are the marquee options — or split a share house with friends, which is the classic Fire Island move. Book early: the island's limited lodging sells out months ahead for a marquee June weekend.
Fire Island Bear Weekend is the rare big gay weekend that manages to feel both like a real party and a genuine community reunion — a furry, friendly takeover of the most storied queer island in America. For 2026 it runs June 11–15 across Cherry Grove and the Pines.
Keep planning with our other Fire Island guides:
And browse what's live right now: Fire Island events, Fire Island venues, and the Fire Island city page.
