Fire Island Pines Season Kickoff 2026: Leather Weekend Guide

Fire Island Leather Weekend 2026 Overview

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:

• Dates: Friday, May 15 – Sunday, May 17, 2026
• Location: Cherry Grove, Fire Island (with attendees commuting from the Pines and Sayville)
• Producer: Excelsior MC — New York's leather motorcycle club
• Main event: Mr. Fire Island Leather Contest on Saturday, May 16, 2026
• Host venues: The Ice Palace, Arts Project of Cherry Grove, Belvedere Guest House, Cherry's On The Bay
• Registration: Weekend package from excelsiormc.com/registration
• Benefits: LGBTQ+ non-profits serving Fire Island

A Quick Note on Location (Cherry Grove vs. The Pines)

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.

Leather Weekend 2026 At-A-Glance Schedule

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:

• Friday, May 15 (evening): Welcome social and cocktail hour, followed by the Master and Slave auction — a playful, fundraising-driven kickoff that sets the tone
• Saturday, May 16 (morning): Leather breakfast at a host venue
• Saturday afternoon: Sirs & Cigar social on the boardwalk or back deck
• Saturday cocktail hour: Pre-dinner drinks and community mingling
• Saturday evening: Community dinner, then the headline event — the Mr. Fire Island Leather Contest at the Arts Project of Cherry Grove
• Saturday late night: After-party at The Ice Palace
• Sunday, May 17 (morning): Closing leather brunch and award ceremony
• Sunday afternoon: Farewell drinks, final packing, afternoon ferries back to Sayville

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.

Mr. Fire Island Leather Contest — Saturday, May 16, 2026

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.

What Happens

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.

How to Attend

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.

The After-Party

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.

Venues You'll Be In All Weekend

The Ice Palace — The Late-Night Anchor

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.

Arts Project of Cherry Grove — The Contest Venue

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 On The Bay — Daytime Socials

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.

Belvedere Guest House for Men — Host Venue and Stay

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 — Casual Meals

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.

Registration, Tickets & Costs

Weekend registration is handled through Excelsior MC's registration page. Historically the package includes:

• Access to all event activities at participating venues
• Five community-centered meals across the weekend
• A Fire Island Leather Weekend pin
• Entry to the Mr. Fire Island Leather Contest
• Eligibility for prize drawings

Early bird pricing closed January 31, 2026. Standard registration typically remains open up to the weekend itself, with prices stepping up as May approaches.

What's NOT Included

Registration covers event activities and meals inside the program. It does not cover:

• Your ferry tickets (round-trip Sayville Ferry to Cherry Grove)
• Lodging (book separately — see below)
• Meals outside the program
• Gear and optional extras

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.

Where to Stay for Leather Weekend

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.

Cherry Grove Options (Closest to Events)

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.

Fire Island Pines Options (Short Walk Away)

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.

Getting There

Fire Island is car-free. The only way to arrive is the same way everyone has for a century: train, then ferry.

From Manhattan

1. LIRR from Penn Station or Jamaica to Sayville (about 90 minutes)
2. Sayville taxi or shuttle to the ferry terminal (5 minutes, roughly $5–10 per person)
3. Sayville Ferries to Cherry Grove (or to the Pines if you're staying there). The crossing takes about 30 minutes
4. On arrival: you walk. Luggage carts are available at both docks — bring one for heavy gear bags

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.

From JFK or LaGuardia

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.

Ferry Schedules

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.

What to Pack

Fire Island in mid-May is a weather coin flip. Pack for both days.

• Leather: Whatever you wear for the contest, the socials, and the after-party. The weekend is formal leather when called for and play leather the rest of the time
• Layers: 60s during the day, 40s at night isn't unusual in mid-May. A warm jacket over your harness is entirely normal on Friday
• Waterproof shoes or boots: The boardwalks are wood, the beach is sand, and a May rainstorm soaks sneakers fast
• Flashlight or headlamp: No streetlights on the wooded paths after dark
• Reusable water bottle: Bottled water gets expensive fast on the island
• Cash: Cards work most places but some longtime venues are still cash-preferred, especially for tips
• Printed tickets and registration confirmation: Cell service drops out in parts of the Grove — don't rely on pulling things up at the door

Is Leather Weekend Right for You?

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.

Other Fire Island Events to Combine With

Leather Weekend is the opener — these are the other signature weekends on the 2026 calendar:

• Fire Island Bear Weekend — June 11–14, 2026 (both communities)
• Invasion of the Pines — July 3–5, 2026 (Cherry Grove to Pines ferry tradition)
• Pines Party — July 31 – August 2, 2026 (the flagship circuit party on the beach)
• Ascension — August 2026 dates TBA (Pines party weekend)
• Spartacus — September 2026 (season closer at the Belvedere)

Full schedules, venues, and travel logistics for every one of these are in our Fire Island 2026 events guide.

Frequently Asked Questions

When is Fire Island Leather Weekend 2026?

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.

Where on Fire Island does Leather Weekend take place?

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.

Who produces Fire Island Leather Weekend?

The weekend is produced by Excelsior MC, New York's leather motorcycle club. Proceeds benefit LGBTQ+ non-profits serving Fire Island.

How do I register for Leather Weekend 2026?

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.

Do I need to be in leather to attend?

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.

What's the Mr. Fire Island Leather Contest?

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.

Is Fire Island fully open in mid-May?

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.

Where should I stay for Leather 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.

Can I visit Fire Island for just one day during Leather Weekend?

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.

How much does Leather Weekend cost all-in?

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.

What else should I plan around in May 2026?

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.