Part of the Gay Fire Island Guide — bars, events & things to do.
Friday, May 15, 2026
Cherry Grove, Fire Island
Fire Island, NY 11782Let people know you're going, see who else is attending, and share the event with friends.
Catch your city's vibe or the global LGBTQ+ scene.
No spam, unsubscribe anytime.
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.Before the ferries fill with Memorial Day crowds, before the tea dances pack the Blue Whale, before the first Invasion queens board the boats in July — Leather Weekend happens. Held every May in Cherry Grove and produced by the brothers of Excelsior MC, Fire Island Leather Weekend is the quiet, community-driven event that unofficially opens the summer season for both Cherry Grove and Fire Island Pines. It's the first weekend of the year that the Ice Palace flips the lights back on, the first weekend the Grove Hotel rooms book out, and the first weekend that leathermen from across New York (and well beyond) show up to claim their corner of the island before the high-summer rush.
This isn't a circuit party. There's no beach stage, no thousand-person pool party, no DJ lineup being traded on Instagram. Leather Weekend is three days of community dinners, cocktail socials, the legendary Mr. Fire Island Leather contest, and the kind of conversations you can only have when the ferry count is low and the vibe is still unhurried. If you've never done Fire Island and you want to start with something warm and welcoming, this is the weekend.
Here's what you need to know for 2026:
Pro Tip
Leather Weekend falls a full week *before* Memorial Day (May 23–25). Not every island business is open yet — some restaurants run limited hours, the first ferries of the day may still be on spring schedules, and weather can swing between "beach day" and "bring a jacket." Plan your meals and transit around what's actually open. See the full season calendar in our [Fire Island events guide](https://outxout.com/blog/fire-island-pride-events-2026).
If you've booked in the Pines and now you're wondering where exactly all of this happens: the formal Leather Weekend events are hosted in Cherry Grove, the more diverse and historically working-class of Fire Island's two LGBTQ+ communities. The Pines — upscale, party-forward, circuit-adjacent — is a 15-minute walk away through the wooded path locals call the Meat Rack, or a short water taxi by bay.
The good news: the two communities work as one long weekend. Plenty of Leather Weekend attendees stay in the Pines for the accommodations (The Madison, Pines Bluff Overlook) and walk or water-taxi to Cherry Grove for the events. Others stay in the Grove's historic guesthouses — The Belvedere, The Grove Hotel, Dune Point — because they're literally next door to the contest venues. Either way works. If you're entirely new to Fire Island, read our full LGBTQ+ guide to Fire Island before booking so you understand how the two communities fit together.
The full schedule is published on the Excelsior MC weekend schedule page closer to the event. Based on the 2025 program and years prior, here's the shape of the weekend you can plan around:
Your registration covers access to all of the above plus five community-centered meals, an event pin, and any prize drawings. Confirm exact times and ticketed vs. open events on the Excelsior MC event page once 2026 details go live.
Follow Fire Island's Full Season
Leather Weekend is only the first of seven signature weekends on Fire Island. Follow along and find every event, party, and venue on Out x Out.
The Mr. Fire Island Leather Contest is the heart of the weekend. It's a title with decades of history — the contest history page lists winners going back to the club's early years — and it doubles as the main fundraising vehicle for the weekend's LGBTQ+ non-profit beneficiaries.
Contestants present to a panel of judges and a full audience at the Arts Project of Cherry Grove — the historic community theater on Main Walk — across the traditional leather contest categories: formal leather, presentation, question-and-answer, and crowd response. The house is packed, the energy is big, and the titleholder walks away as an ambassador for Fire Island's leather community for the year ahead.
Most Leather Weekend registrations include access to the contest. If you're on the island and not formally registered, check whether day-of tickets to the contest itself are released — they often are — and arrive early. Seating is limited, and the community reserves front rows for sponsors, judges, and club brothers.
Pro Tip
The Arts Project isn't just a contest venue — it's one of Cherry Grove's most beloved community institutions, founded in 1948 and still producing year-round LGBTQ+ theater. Even if you're not into leather contests, it's worth a visit during the weekend just to see the space.
After the contest wraps, the crowd rolls over to The Ice Palace — the Grove Hotel's beloved nightclub and the first dance floor to open on the island every season. Expect the music to shift from contest-formal into a full-on celebration. This is the night the season feels like it's started.
The Ice Palace is Cherry Grove's iconic nightclub, attached to the Grove Hotel and open seasonally from May through September. During Leather Weekend it hosts the Friday social and the Saturday post-contest after-party. Drag shows, dance floor, outdoor patio, and the unmistakable "we just got here" energy of the first weekend of the year.
Home of the Mr. Fire Island Leather Contest and a national landmark in LGBTQ+ community arts. The room holds a few hundred people when packed, and the acoustics and sightlines make it a genuinely good contest space — not just a repurposed bar.
Cherry's is the Grove's beloved bayside bar and a frequent Leather Weekend daytime host. Expect it to be on the schedule for a cocktail hour, a brunch, or both. The deck faces the Great South Bay and is one of the best sunset spots in either community.
The Belvedere is both a historic all-male guesthouse and one of the weekend's regular host venues (particularly for Sunday brunch and private member events). If you're coming with a leather club, there's a good chance a gathering will land here.
Island Breeze is Cherry Grove's casual beachfront restaurant and bar — a good bet for a daytime meal between weekend events, or a quick drink on the deck before heading back out.
Fire Island, New York
Fire Island, New York
Fire Island, New York
HotelFire Island, New York
Fire Island, New York
Weekend registration is handled through Excelsior MC's registration page. Historically the package includes:
Early bird pricing closed January 31, 2026. Standard registration typically remains open up to the weekend itself, with prices stepping up as May approaches.
Pro Tip
Register directly through Excelsior MC rather than trying to piece the weekend together event-by-event. The bundled package almost always works out cheaper once you factor in five meals, contest entry, and venue access — and it's how you support the club's fundraising for Fire Island LGBTQ+ non-profits.
Registration covers event activities and meals inside the program. It does not cover:
Budget roughly $400–$700 per person for the weekend all-in if you're staying in a shared guesthouse room, more if you're in a private rental.
Leather Weekend draws far smaller crowds than Invasion or Pines Party, which means lodging is easier to secure than in peak summer — but it's also the opening weekend of the season, and the Grove's few guesthouses book out fast. Plan to reserve by late February or early March at the latest.
The Grove Hotel is the obvious pick for Leather Weekend — it's the same complex as The Ice Palace, meaning the Friday night social and Saturday after-party are literally downstairs. Rooms are modest, the vibe is unpretentious, and it's the only hotel where you can roll into bed 30 seconds after the dance floor closes.
The Belvedere Guest House for Men is the historic all-male guesthouse of Cherry Grove and a regular weekend host. If you want to be in the center of leather-community lodging and don't mind a shared bath, this is the pick.
Dune Point Guest House is the more laid-back third option — cozier, quieter, and good for couples or anyone who wants a retreat to come back to after long nights out.
If the Grove properties are booked, or you'd rather base yourself in the Pines and commute for the events, The Madison Fire Island Pines is the most reliable full-service hotel on the Pines side. Expect a 15-minute boardwalk walk or short water taxi to Cherry Grove for the contest and after-party.
For a full breakdown of every guesthouse, house share option, and seasonal rate across both communities, see our Fire Island hotels guide.
Pro Tip
If you're walking between the Pines and Cherry Grove after dark, use the beach or the main boardwalk — not the Meat Rack — unless you know the path. The wooded route is unlit and confusing after a few drinks, and the beach walk at night is honestly one of the best parts of Fire Island.
HotelFire Island, New York
HotelFire Island, New York
Fire Island is car-free. The only way to arrive is the same way everyone has for a century: train, then ferry.
Plan for about 2.5 to 3 hours total door-to-dock from Midtown. On the Friday of Leather Weekend, the 4–6 PM ferries are the busiest.
Take the LIRR Port Washington branch transfer or a rideshare to Sayville. JFK is the easier connect — Jamaica Station is directly on the LIRR Montauk branch.
Early-season ferries often run on reduced weekday schedules, with service expanding over Memorial Day weekend. Always check the Sayville Ferry schedule the week of your trip — the Friday evening lineup is the most important ferry to catch.
Pro Tip
Aim for the 4:30 or 6:00 PM Friday ferry from Sayville to arrive in time for Leather Weekend's welcome social. The last ferry of the night runs earlier than you'd expect in May — missing it means an expensive water taxi or a night in a Sayville hotel.
Fire Island in mid-May is a weather coin flip. Pack for both days.
Leather Weekend is particularly good for three groups of people:
First-timers on Fire Island. The small crowds, communal meals, and welcoming culture make it a gentler entry to the island than Invasion or Pines Party. You'll meet people, eat with them, and leave with a sense of how Fire Island actually works before you return for the bigger weekends.
Leather-community regulars. If you're already part of a club — Excelsior, Empire City MC, Conductors NY, or any of the regional clubs — this is the weekend where everyone shows up. Club colors come out, brothers reconnect, and the network is tight.
Season openers. Locals, homeowners, and repeat visitors who want to get back to the island before the summer crowds arrive. Leather Weekend is a soft landing — the shops are still quiet, the beaches are empty, and the boardwalks feel personal again.
It's less ideal if you're looking for a full-throttle circuit weekend or a nonstop dance-floor experience. For that, point yourself at the Pines Party in late July or Invasion on July 4.
Pro Tip
Newcomers often ask if they need to "look a certain way" to come to Leather Weekend. The answer is no — Excelsior MC has consistently made a point of welcoming leather-curious first-timers, and the weekend is built around community meals and open socials. If you want to wear full leather, wear it. If you want to wear jeans and a t-shirt to your first event and ease in, that works too.
Leather Weekend is the opener — these are the other signature weekends on the 2026 calendar:
Full schedules, venues, and travel logistics for every one of these are in our Fire Island 2026 events guide.
Plan Your Whole Fire Island Season
Find every event, venue, and LGBTQ+ hotspot on Fire Island — from Leather Weekend through Labor Day — on the Out x Out app.
Fire Island Leather Weekend 2026 runs Friday, May 15 through Sunday, May 17, 2026. It's the earliest major LGBTQ+ event on Fire Island and opens the summer season for both Cherry Grove and Fire Island Pines.
Leather Weekend is hosted in Cherry Grove, at venues including The Ice Palace, Arts Project of Cherry Grove, Cherry's On The Bay, and the Belvedere Guest House. Attendees staying in Fire Island Pines typically walk or water-taxi the ~15 minutes to Cherry Grove for events.
The weekend is produced by Excelsior MC, New York's leather motorcycle club. Proceeds benefit LGBTQ+ non-profits serving Fire Island.
Registration is handled on the Excelsior MC registration page. Early bird pricing ended January 31, 2026; standard registration typically remains available up through the event. Your registration includes access to all event activities, five community meals, and entry to the Mr. Fire Island Leather Contest.
No. While many attendees wear leather — from full formal leather at the contest to play gear for late nights — the weekend is open and welcoming to newcomers, leather-curious first-timers, and anyone who wants to support the community and have a good time. The vibe is inclusive by design.
The Mr. Fire Island Leather Contest is the weekend's headline event, held annually at the Arts Project of Cherry Grove. Contestants present across traditional leather contest categories, and the winner serves as an ambassador for the Fire Island leather community for the year ahead.
Not entirely. Leather Weekend falls a full week before Memorial Day, so some restaurants, shops, and services are still on pre-season schedules. The Ice Palace, Cherry's On The Bay, and the main guesthouses open in time for the weekend, but expect limited hours elsewhere. Confirm your dining plans in advance and don't count on every venue being active until the following weekend.
The easiest option is The Grove Hotel in Cherry Grove — it's the same building as The Ice Palace and puts you at the center of every event. The Belvedere Guest House for Men is the classic leather-community stay. Dune Point is the quieter option. For a full breakdown, see our Fire Island hotels guide.
Technically yes — the last ferries back to Sayville run late enough that a Saturday day trip is possible — but you'll miss the community dinners, the contest, and the after-party, which are the best parts. Stay at least Friday and Saturday night to get the real experience.
Budget roughly $400–$700 per person for a two-night shared-room stay including registration, ferry, and basic meals. Private rooms or solo travelers should budget $600–$1,000. Compare this to the $1,200+ you'll spend on Pines Party weekend — Leather Weekend is one of the most accessible signature events on the Fire Island calendar.
May 15–17 is the only major LGBTQ+ event on Fire Island in May 2026 — Memorial Day the following weekend is unofficially the start of the wider season, but there's no single headline event. If you want to stack trips, see our full Fire Island 2026 events calendar.
Ready to plan the rest of your Fire Island 2026? Start with our LGBTQ+ guide to Fire Island, browse every LGBTQ+ event on Fire Island, or explore Cherry Grove and Pines venues.
