The big gay Halloween weekends of 2026

The short version

Halloween falls on a Saturday in 2026, so most of the big celebrations land on the same night: Oct 31. Pick one, book the bed now, and plan your costume around the rules of the place you're going (they differ more than you'd think).

Dates and details here are for 2026. Most of these come back around the same weekend every year, so if you're reading this after Halloween, check each event's own site for next year's dates.

Fantasy Fest, Key West (Oct 16–25)

Ten days of costumes across the island, ending the weekend before Halloween. The 2026 theme is "Musical Icons and Iconic Musicals." The final stretch is the big one:

• Thu Oct 22: the 43rd Headdress Ball, hosted by the Key West Business Guild (the island's LGBTQ+ business group), at the Coffee Butler Amphitheater, Truman Waterfront Park. Doors 6:30 pm, show 8 pm.
• Fri Oct 23: the Masquerade March, the "locals' parade" through Old Town. Paparazzi Row warms up at Fleming and White from 4 pm; step-off is 5:30 pm, ending at the Duval Street fair.
• Sat Oct 24: the Fantasy Fest Parade steps off at 7 pm on Duval Street. Watching from the street is free; bars and hotels along the route sell balcony and viewing parties.
• Sun Oct 25: "The Fat Lady Sings" tea dance at La Te Da, 4–8 pm, billed as the last official event.

The gay bars and guest houses run their own parties all week, from pool parties at the Bourbon St. Pub to events at Island House. The official schedule at fantasyfest.com lists them with times and prices.

Getting around: almost everything downtown is less than a 15-minute walk from everything else. Locals bike; if you do, use a light after dark. Taxis and rideshares pick up and drop off at or east of Simonton Street, so walk that way before you call one. City garages (Old Town, Mallory Square, Key West Bight) list $48 a day, and special-event rates may apply. Who it suits: people who want a whole week of it and don't mind heat or crowds. Plan it: Key West 101, gay guest houses, Duval Street bars. Missed it? 2027 is Oct 22–31.

Spooky Bear, Provincetown (Oct 29–Nov 1)

The town and the Spooky Bear weekend (produced by the Northeast Ursamen) host four days of parties, ghost tours, dances, shows, trick-or-treating and a costume ball. At the Crown & Anchor, a weekend pass covers Friday's Costume Ball and Meatball's Fat Slut party; the town calendar lists Fat Slut on Thursday Oct 29 and the pass page puts it on Saturday, so check the date when you buy.

Who it suits: bears, cubs, their admirers and their friends, plus anyone who likes P-town better once the summer crowds have gone home. Late-season P-town is quieter than summer, which is half the appeal.

Practical: by late October the Bay State Cruise Co. fast ferry from Boston runs weekends only (in 2026: Friday, Saturday and Sunday, plus an extra Thursday sailing on Oct 29), and high wind can cancel sailings, so have a plan B such as driving. Pack layers for walking Commercial Street at night. Plan it: Provincetown 101, guest houses, bars, and the full list at ptown.org.

Halloween New Orleans (Oct 30–Nov 1)

One of the country's longest-running LGBTQ+ fundraisers. It began in 1983 as a dinner party honoring friends lost to HIV/AIDS, and it has raised more than $5 million for Project Lazarus, the oldest and largest agency providing housing and wraparound support services to people living with HIV/AIDS in the area. The 2026 weekend:

• Fri Oct 30: the Lazarus Ball gala, 7–10 pm, at The Barnett.
• Sat Oct 31: the Halloween Party, 10 pm–3 am, at The Fillmore.
• Sun Nov 1: the Tea Dance, 1–4:30 pm, at Goldring Woldenberg Riverfront Park (Gov. Nicholls St. Wharf).

Who it suits: people who want a party with a purpose, in a city that already takes costumes seriously. The Sunday tea dance is an easy way in if late nights aren't your thing. Passes are sold at halloweenneworleans.com. Plan it: New Orleans city guide, where to stay.

West Hollywood Halloween Carnaval (Sat Oct 31)

More than 100,000 people in costume on Santa Monica Boulevard between Doheny Drive and La Cienega Boulevard, 6–11 pm, with a DJ stage and food trucks at San Vicente. It's free and needs no ticket. After 11 the party moves into the bars and clubs.

• Leave at home: backpacks, camera cases and tote bags (clear plastic bags are fine), weapons, fireworks and drones. No drinking on the street; you can still go into the bars.
• Getting there: parking mostly disappears. The free WeHo Halloween Ride runs 6 pm–3 am along Santa Monica Boulevard between La Brea and Kings Road, and some vehicles link to the Hollywood/Highland Metro station until midnight.
• The city recommends leaving kids and pets at home.

Who it suits: people who love a crowd and want a huge audience for their costume. Plan it: LA city guide (WeHo's bars are in it), where to stay, /b/la for who's going where.

Haunted Halsted, Chicago (Sat Oct 31)

The Haunted Halsted Halloween Parade turned 30 in 2026, and that year it became an all-day affair in Northalsted, with a new daytime fest:

1. 11 am–10 pm: a free street fest on Halsted from Aldine to Brompton, with vendors, music, drinks (21+ with ID), and a kids' zone with trick-or-treating.
2. 6 pm: the street clears for the parade; find a spot behind the barricades.
3. 7 pm: the parade starts at Halsted and Belmont and ends at Brompton.
4. 8 pm: costume contest and after-party at 3514 N. Halsted, with $4,000 in prizes across five categories (character, creative, scary, group and youth). Entry is $5; sign up online or at the registration tent (3211 N. Halsted) from 2 pm.

It goes ahead in rain or snow. Who it suits: almost everyone, including families in the daytime and groups who want to enter as a team. Halsted is closed to traffic from 10:30 am, so take the CTA. Plan it: Chicago city guide, where to stay.

Two more worth knowing

Planning it at the last minute

• Lock in the bed first. Everything else can be improvised; a room on Halloween weekend can't. Start with our gay-friendly stays by destination, and ask the guest house directly if a booking site shows nothing: small places sometimes have a cancellation.
• Stay a train ride away. In New York, Chicago and LA, a hotel a few stops out on the subway, the CTA or the Metro is often easier to find than one on the parade route, and you'll sleep better too.
• Split it. A two-bedroom rental shared with friends can cost less per person than one hotel room, and it gives you somewhere to get dressed together.
• Pick your bars before the night. Lines get long fast. Browse the bar finder and the calendar, choose a first stop and a backup, and check each bar's own page for ticketed parties.
• Go local. If travel isn't happening, your own city probably has a costume night. Your city guide and board are the place to ask.

Costumes without stress

• Start from what you own. One bought piece (a hat, a wig, a cape) plus clothes from your closet beats a bagged costume that rips by 9 pm.
• Dress for the street, not the photo. You'll be standing and walking for hours. Comfortable shoes, somewhere to keep your phone and ID, and in P-town or Chicago, a layer you can put on without ruining the look.
• Read the rules first. Fake weapons are banned at Fantasy Fest and weapons at WeHo, which rules out a lot of swords, guns and pitchforks. Bags are restricted at both. In New York, a costume is your ticket to march.
• Skin is optional. Plenty of the best costumes cover everything. Wear what makes you feel good, not what you think the crowd expects.
• Go as a group. A theme with your partner or friends takes the pressure off any one person, and it makes you easy to find in a crowd. "We're the Golden Girls" is also a great opener.
• Skip other people's cultures and identities as costumes. Characters, puns and pop culture are wide open.

Look after yourself (and each other)

Crowds can be a lot. It's fine to step into a side street, watch from a balcony party or call it early. More on pacing a big party weekend in our circuit guide.

Rather keep it low-key?

Some of the best Halloweens happen in someone's living room. A few ideas:

• Host a costume-optional night: a horror double feature, a pumpkin-carving table and one big pot of chili. Let people come in pajamas if they want.
• Game night with a twist: a murder-mystery party kit or a spooky board game, with a small prize for best costume.
• Hand out candy with your partner or roommates in matching costumes. Neighbors remember this.
• Go see Rocky Horror or a drag show: lots of local bars and cinemas run them around Halloween.

Looking for something nearby tonight? Try What should I do tonight?, or ask in Friends & Community or your city board who's hosting.

Where this might not fit

• If you're not out, remember these are photographed and filmed events: the New York parade airs live on NY1, and Fantasy Fest has a whole "Paparazzi Row." A mask helps, but a house party may suit you better.
• If you're sober or don't drink much, look at the daytime side: Haunted Halsted's afternoon fest, the New Orleans tea dance, or watching the Key West parade from the street.
• If crowds or long stretches on your feet are hard, a ticketed viewing party, a balcony or a smaller weekend like Spooky Bear will be kinder than WeHo or Sixth Avenue.
• If money's tight, the street parties (WeHo, Chicago, New York, the Key West parade) are free. Lodging is the real cost, so a local event can beat a flight.
• If you're bringing kids, Chicago's daytime fest is built for families. West Hollywood recommends leaving kids at home.

On the calendar

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