Spooky Bear Weekend
Provincetown hosts a multi-day Halloween celebration featuring parties, dances, a haunted house, a costume ball, and other seasonal events across town. The weekend overlaps with Spooky Bear, an annual gathering produced by the Northeast Ursamen that includes costume contests, themed parties, and nightlife-focused meetups. Events are hosted at various local venues including the Crown & Anchor, The Yoga Joint, and local walking tour operators.
More Events in Provincetown During Spooky Bear Weekend
Piano Bar Tori & Chris
Piano Bar with Tori & Chris is the Wednesday sing-along at Gifford House in Provincetown, where the piano's yours to lean on and the room joins in on the chorus. Settle in at the Porch Bar with a cocktail and let the showtunes roll. It starts at 9pm, and you'll be glad you came early for a seat near the keys.
Club Fag Bash
Wednesday night at Gifford House gets rowdy — Club Fag Bash is the weekly reset for anyone who wants to dance hard, drink well, and spend the night surrounded by people who actually know how to have a good time. Rotating DJs keep the energy up in Purgatory downstairs, and the vibe is reliably packed and unapologetically fun.

Solid Gold Tea Spooky Bear Weekend
Destroy Mona
Destroy Mona is a drag and cabaret night at Gifford House in Provincetown, and it's exactly the kind of show that makes you forget you ever had plans for the evening. Settle into the Wilde Playhouse for live performance, then float downstairs to Purgatory after the curtain if you want to keep the energy going. It runs Thursday, October 29, starting at 6:30 PM.
Ursamen Early Bear Meetup
Ursamen's Early Bear meetup at Gifford House in Provincetown is the low-key way to start your Thursday night among bears and bear-curious men. It's a casual gathering built for connecting before the night picks up steam, so you can catch up with familiar faces or meet new ones over a drink at the Porch Bar. Show up at 8pm and let the night unfold from there.

I Know Who You Did Last Summer
Liza Lott and Raquel Blake team up for a filthy, fabulous parody that turns a '90s slasher into pure camp chaos. Four famous friends accidentally kill the Gorton's Fisherman at Dick Dock, dump the body, and swear to silence—until a mysterious note, a giant hook, and spectacularly bad decisions threaten to expose them a year later. Expect celebrity shade, '90s nostalgia, musical numbers, and a bloodbath that's more mayhem than murder. Lucky Devil Theater Company (20 years of Provincetown comedy gold) knows how to deliver the laughs.
Piano Bar with Britanny & Clint
Piano Bar with Britanny & Clint is a Thursday sing-along at Gifford House in Provincetown, where the Porch Bar's piano becomes the center of the night and everyone's invited to join in. Pull up a stool, grab a cocktail, and sing the chorus you've been humming all week. It starts at 9:00 PM on Thursday, October 29, 2026, and you'll want to get there early for a good seat.
Townie Masquerade Ball
Townie Masquerade Ball is Provincetown's costumed night out at Gifford House, where a mask makes everyone a little bolder and the local crowd turns up to play. It starts at 9pm on Thursday, October 29th, 2026, with costumes, dancing and plenty of Provincetown's own on the floor. Pick a mask that's just a little too much, then head downstairs to Purgatory and let the DJ take it from there.

Fat Slut Spooky Bear
LA drag superstar Meatball brings her legendary party to Provincetown for Spooky Bear season. Expect drag shows, gogo dancers, a packed dance floor, and the original sexy food eating competition — bears doing what they do best, which is party hard and have zero apologies about it.

Furball: Howl Underwear and Gear Party
Furball is the legendary dance party that's been running for over 17 years — a sweaty, sexy celebration of everything furry and fuzzy. Brooklyn Joe brings the party back to Provincetown with gogo daddies, cubs, and a crowd that knows how to have a good time. Leather and gearwear encouraged. Last year sold out, so grab your tickets.
Townie Masquerade Ball Halloween 2026
Halloween at Gifford House in Provincetown, Thursday, October 29, 2026 from 10 PM. Live piano bar music, autumnal games and spooky fun in the yard, and a ball in club Purgatory with DJ William Francis. Bring your best mask. 21+, free with RSVP.

Club Himbo (Jockstrap)
Thursday night at Gifford House belongs to the jocks and the people who love them. Club Himbo is the kind of dance floor where the vibe is unapologetically masculine, the music keeps things moving, and everyone's here to have a genuinely good time without the pretense. Late night, rotating DJs, and a crowd that knows how to celebrate.

HalloQueen Burner Brunch with Tina Burner
Tina Burner headlines HalloQueen Burner Brunch at The Crown & Anchor in Provincetown on Friday, October 30. Doors open at 10:30 AM and the first-seating show starts at 11:00 AM. Ticket price does not include food or beverages, so order a cocktail and come dressed to slay.

HalloQueen Burner Brunch 1PM Spooky Bear
HalloQueen Burner Brunch with RuPaul's Drag Race All Star Tina Burner returns to The Crown & Anchor in Provincetown on Friday, October 30 for the 1:00 PM second seating, with doors at 1:00 PM and the show starting at 1:30 PM. Expect live drag, comedy and plenty of Halloween camp, and come in costume if you like. Ticket price does not include food or beverages, so plan to order from the menu.
All Hallows Tea with Charlene & Tyler Ashley
Swap the spooky-season scramble for a proper afternoon tea, with drag queens Charlene and Tyler Ashley hosting a Halloween-themed sitting at Gifford House in Provincetown. It's a playful, costume-friendly way to spend a Friday afternoon, with the performers keeping things lively between sips. The tea starts at 2:00 PM on Friday, October 30, 2026, so bring your sense of humor and your best teacup manners.

Halloween Uniform Tea: Spooky Bear Weekend

Ravi Round The World: An Influencer in the Wild
Award-winning storyteller Ravi Roth brings his wildly popular cabaret to the Red Room stage—a theatrical fever dream equal parts Broadway confession booth and influencer memoir. From small-town Scranton to The New York Times, he unpacks the messy, musical, occasionally thirsty pursuit of love, validation, and viral moments across continents. Directed by Cheryl Stern with music direction by Michael Ferrara, expect powerhouse vocals, laugh-out-loud honesty, and the kind of vulnerability that only happens when the filter comes off.
Marti Gould Cummins: Stranger Queen
Marti Gould Cummins brings Stranger Queen to Gifford House in Provincetown on Friday, October 30, 2026, at 6:30 PM. The show runs at Wilde Playhouse, one of three spaces inside the historic venue. Check the venue for ticket details and any age or access notes before you go.

Witch Perfect Show
An all live-singing comedy parody of the cult-classic Disney film Hocus Pocus, featuring Emmy-winning stars from RuPaul's Drag Race. Expect hits from Lady Gaga, Madonna, and Cher, plus Broadway standards and a show-stopping rendition of "I Put a Spell on You." Doors at 6:30 PM, show at 7:00 PM.

Tammie Brown's Halloween Spooktacular
Tammie Brown brings her annual Halloween tradition to the Red Room stage — a night of drag performance that's become a Provincetown fixture. Expect the irreverent energy and theatrical flair that made her a standout on RuPaul's Drag Race, all dressed up for the spookiest night of the year.

Spooky Cher
Thirsty Burlington—the legendary live-vocal Cher impersonator and Provincetown fixture for over 25 years—returns for one night only in full Halloween drag. Known for her uncanny visual likeness and powerhouse vocals, Thirsty's story inspired the indie musical film of the same name. Proceeds benefit Thirsty Burlington and her continued health journey. Door at 8:15 PM.
Fag Bash Halloween Edition w/ DJ Prosumer Charlene Father Figure & Ross Millam
Fag Bash Halloween Edition is the Provincetown dance party where Halloween Friday gets its loudest, most dressed-up crowd. DJ Prosumer Charlene, Father Figure and Ross Millam take turns on the decks from 9:00 PM at Gifford House, and the real action is downstairs in Purgatory, where the floor fills fast. Come in costume, arrive ready to move, and don't plan on leaving early.
Movie Night Double Feature in the Wilde
Movie Night Double Feature in the Wilde is a Friday night at Gifford House's Wilde Playhouse in Provincetown, where the big screen takes over and you get two films for the price of your evening. Grab a seat in a room with real history in its floorboards, settle in, and let the lights go down. It starts at 9:00 PM on Friday, October 30th, 2026, so come early enough to claim your spot.

Mother Disco Spooky Bear
MotherDisco brings its signature NYC energy back to Provincetown for Dead Disco Prom, a Halloween takeover built for dancing. Dress up in your spookiest, most glamorous looks and spend the night moving to a high-energy mix of disco, house, and queer nightlife favorites. Expect a packed dance floor, killer outfits, and the kind of sweaty, joyful chaos that makes MotherDisco legendary.
Piano Bar Tori Mclean & Chris Grasso
Piano Bar with Tori Mclean and Chris Grasso is the night to pull up a stool, grab a drink and sing your heart out to showtunes you know by heart. It starts at 9:30 PM on Friday, October 30th at Gifford House in Provincetown, where the piano room has been a storied queer gathering spot for years. Bring your best showtune, and expect a crowd that knows every chorus.

Belly: Spooky Bear Edition
BELLY is back in Provincetown for Bear Week 2026—a night built for bears, chasers, and anyone who loves a good time. Expect drag, killer beats, surprises, and the kind of inclusive, unapologetic party energy that makes this event legendary. Come in your best gear or just bring your bold, beautiful self; the dance floor and the crowd will take it from there.
Club Disco Night
Disco takes over Gifford House's dance floor for the night — expect spinning vinyl, a packed room ready to move, and that specific magic that happens when a crowd gets locked into a groove. Perfect for anyone who wants to dance without overthinking it.
Goldiloxx Tricks & Treats
Goldiloxx Tricks & Treats is the Halloween party at Gifford House in Provincetown, where costumes are the point and the whole building gets in on the spooky fun. Start on the porch with a cocktail, catch a show at the Wilde Playhouse, then head downstairs to Purgatory for the dance floor. It kicks off at noon on Saturday, October 31, so you'll want to be in costume early.

Spooky Bear Weekend Tea Dance

Witch Perfect Show
Halloween night gets the full drag treatment with this all-live-singing Hocus Pocus parody featuring Emmy-winning RuPaul's Drag Race stars Tina Burner, Scarlet Envy, and Alexis Michelle as the Sanderson Sisters. Expect a theatrical mashup of Lady Gaga, Madonna, Cher, Disney classics, Broadway showstoppers, and the sisters' own fierce take on "I Put a Spell on You." Doors at 6:30pm, show at 7:00pm.
Piano Bar Lily May Harrington
Piano Bar with Lily May Harrington is the Saturday night where the whole room ends up singing the chorus, whether you planned to or not. Grab a cocktail at Gifford House in Provincetown, pick the Porch Bar or Wilde Playhouse upstairs for the night, and settle in for showtunes and sing-alongs. It starts at 8:00 PM on Saturday, October 31st, and Halloween is the perfect excuse to show up in costume.

Dark Rooms: Jackie Cox
RuPaul's Drag Race Season 12 alum Jackie Cox brings her bold, boundary-pushing drag to the Red Room stage. Known for fearless fashion choices and sharp performance instincts, Jackie's a performer who doesn't play it safe — expect intelligence, artistry, and the kind of drag that actually says something.
The Underwear Party: Spooky Bear 26 Edition
Halloween night at Gifford House gets gloriously rowdy — the Underwear Party is exactly what it sounds like, a packed dance floor where the dress code is minimal and the energy is maximum. Rotating DJs keep the vibe going, the crowd is ready to let loose, and it's the kind of night that becomes a story you're still telling weeks later.
Club Underwear Party
Halloween night at Gifford House gets gloriously uninhibited — this underwear-themed dance party brings the kind of playful energy that only happens when everyone's dressed (or undressed) for the occasion. Expect packed dance floors across multiple rooms, rotating DJs, and a crowd that knows how to celebrate.

Death Becomes Them Costume Ball
Halloween gets glamorous at this Roaring Twenties costume ball — a night of drag performances, dancing, and deliciously dark surprises. Jan Sport, Tina Burner, and Jackie Cox headline the stage while Jake Glass and VJ Tom Yaz keep the energy high. Enter the costume contest for a shot at the $500 grand prize. Come glamorous, come ghoulish, come dressed to kill.

Possessed 7
Provincetown's biggest Halloween bash is back for its seventh year, and this time it's massive. Three clubs running simultaneously—the Graveyard, the Catacombs, and the Cornfield Drag Barn—plus a new VIP Balcony Lounge. Hosted by Tammie Brown and Jackie Cox, expect dancing, live DJs, themed pop-up performances, and a $1,000 cash prize for the best costume. Doors open at 9:45 PM; tickets start at $15 for early presale.

Underwear Night
Provincetown's favorite underwear party takes over Club Purgatory every Saturday night. Strip down, dance hard, and feel the energy of a packed floor with DJ Father Figure spinning all night long. Clothing check starts at 9pm in the Wilde Theater upstairs before the party moves downstairs to the dance floor, running until close. Unapologetically sexy, fun-first, and uninhibited — it's the night that keeps everyone coming back week after week.

Tryster Act: A Not So Holy Brunch
Sunday brunch just got a little sinful. The Crown & Anchor's new kitchen opens with RuPaul's Drag Race All Stars Jan Sport, Tina Burner, and Jackie Cox, plus NYC favorite Jarvis Derrell serving powerhouse live vocals, outrageous comedy, camp, and sing-alongs. Grab an all-you-care-to-enjoy gourmet brunch buffet, a cocktail, and your new favorite Sunday in P-Town. $25 minimum spend.

Tryster Act: A Not So Holy Brunch
Provincetown's newest Sunday brunch just got a little sinful. The Crown & Anchor's kitchen is officially open, and it's launching with powerhouse live vocals, outrageous comedy, camp, and sing-alongs hosted by RuPaul's Drag Race All Stars Jan Sport, Tina Burner, and Jackie Cox, plus NYC favorite Jarvis Derrell. Grab a gourmet all-you-care-to-enjoy brunch buffet and a cocktail—this is the Sunday you've been waiting for. $25 minimum spend; tickets don't include food or beverage.
Phoebe Otis Book Launch Party
Phoebe Otis's book launch lands at Gifford House in Provincetown on Sunday, November 1st at 3pm, and it's the kind of afternoon where a new book gets the send-off it deserves. Pull up a seat on the Porch Bar, wander into Wilde Playhouse, and celebrate with the community that loves a good queer story. Grab a drink, say hi to your book club friends, and get your copy signed.

Solid Gold Tea Spooky Bear Wknd

Scarlet Strauss's Boo B Bash
Scarlet Strauss's Boo-B Bash at Red Room in Provincetown brings a stacked lineup of drag legends, including Tammie Brown, Marissa Miller, Jackie Cox and Brittany Rolfs, to the Saki Stage on Sunday, November 1 at 8pm. Expect incredible performances, themed games, giveaways, spooky specialty cocktails and plenty of surprises. You'll want to come in costume, grab a cocktail and get ready for a night of foolishness you won't forget.
Club Leather Night
Purgatory's leather night brings the community together for a no-frills, unapologetic celebration of leather culture. The dance floor stays packed with rotating DJs spinning the soundtrack to the evening, and the crowd knows exactly what it's here for — good music, good people, and the freedom to be fully yourself.

Sunday Service
Gifford House's sexy Sunday night in Club Purgatory — gear up and hit the packed dance floor with DJ William Francis spinning from 10pm late into the night. A weekly late-night ritual of leather, cruising, and nonstop dancing that turns Sunday into the perfect extension of the weekend.
Stay in the loop
Get the best LGBTQ+ events, venues, and community happenings delivered to your inbox.