Provincetown Halloween 2026

Provincetown Halloween Weekend 2026

Over the past several years, Provincetown has become an increasingly popular destination for a Halloween escape. What was once a sleepy weekend in October has become a 4 day festival of parties, costumes and even a Tea Dance. Season doesn’t end anymore after Labor Day!

• Provincetown is the fastest selling destination out of 200 cities on our site. Even the off-season Autumn and Winter events have become popular, so please, don’t delay, book your hotel as soon as possible. Several of the parties take place at The Crown and Anchor hotel and entertainment complex.

Halloween in PTown

• Next Edition: Thursday, October 29, 2026 to Sunday, November 1, 2026
• Provincetown puts its own stamp on Halloween, with elaborate costumes, camp horror shows, drag cabaret and late-night parties.
• Commercial Street becomes part of the entertainment as visitors make their way between restaurants, theatres and clubs in their Halloween outfits.
• Dont miss Horror comedy and drag shows at the Red Room and Crown & Anchor.
• Possessed 7 brings the main Halloween party to the Red Room.
• Sunday brunch and a final club night round off the weekend.
• Arrive on Wednesday for an extra evening at Gifford House.
• Thursday introduces the Halloween comedy programme
• Friday offers a choice of cabaret and shows, and Saturday is the night to bring out your best costume.
• Spooky Bear takes place over the same weekend. Its bear-themed parties, Boatslip teas and selected cabaret performances appear in our separate Spooky Bear guide.
• For a central location between the shows and restaurants, stay at Gabriel’s. Its individually designed rooms and garden courtyards offer a quieter place to return after an evening out.

Where to Stay for Halloween in Provincetown

For Halloween, stay around central Commercial Street or the neighbouring streets near Town Hall. The Crown & Anchor, Red Room and Gifford House are all within a few minutes of one another, making it easy to return to your room between costume changes, cabaret shows and late-night parties.

• The Provincetown Hotel at Gabriel’s – Our top location pick, just behind Town Hall and a short walk from the Crown & Anchor and Red Room. Rooms are individually furnished, some with fireplaces, while the sheltered garden offers a quiet escape from Commercial Street.
• Crowne Pointe Historic Inn & Spa – An adults-only boutique hotel on Bradford Street, particularly convenient for Gifford House and the central clubs. The excellent Shui Spa, hot tub and complimentary cooked breakfast make the mornings considerably more comfortable after a late night.
• Brass Key Guesthouse – One of Provincetown’s best-known LGBTQ+ guesthouses, with elegant rooms surrounding a landscaped courtyard and pool. The Shipwreck Lounge is right on the property for pre-party cocktails, while the main Halloween venues are a short walk away.
• Anchor Inn Beach House – A waterfront guesthouse on Commercial Street with a large front porch and harbour views from selected rooms. Particularly convenient for the Boatslip’s afternoon tea dances, with an easy walk into the centre for evening shows and parties. Check room categories carefully, as balconies, fireplaces and water views vary.

The Halloween  Schedule

Date & Time	Event	Venue
Wednesday 28th October 2026
10 pm	Club Fag Bash	Gifford House, Club Purgatory – Wednesday club night with rotating DJs, for visitors arriving before the main Halloween weekend.
Thursday 29th October 2026
8 pm	I Know Who You Did Last Summer	Red Room – Liza Lott and Raquel Blake star in Lucky Devil Theater Company’s slasher parody, with musical numbers, ’90s nostalgia and a Provincetown twist.
10 pm	Club Himbo: Jockstrap Night	Gifford House, Club Purgatory – Thursday’s jockstrap-themed club night.
Friday 30th October 2026
5.30 pm	Ravi Round The World: An Influencer in the Wild	Red Room – Ravi Roth’s musical cabaret explores travel, relationships and life online. Directed by Cheryl Stern, with musical direction by Michael Ferrara.
7 pm	Witch Perfect	Crown & Anchor – Live-singing drag comedy inspired by Hocus Pocus, combining pop favourites and Broadway numbers. Doors at 6.30 pm.
7 pm	Tammie Brown’s Halloween Spooktacular	Red Room – Tammie Brown’s annual Halloween performance.
10 pm	Club Disco Night	Gifford House, Club Purgatory – Friday’s disco-themed club night.
Saturday 31st October 2026
7 pm	Witch Perfect	Crown & Anchor – Halloween-night performance of the Hocus Pocus-inspired drag comedy. Doors at 6.30 pm.
10 pm	Possessed 7	Red Room – Halloween party across the Graveyard, Catacombs and Cornfield Drag Barn, with a VIP balcony lounge and a $1,000 best-costume prize. Doors at 9.45 pm.
Sunday 1st November 2026
11 am	Tryster Act: A Not So Holy Brunch	Crown & Anchor – First brunch show, with live vocals, drag comedy and sing-alongs. Seating at 10.30 am. Tickets exclude food and drinks; $25 minimum spend.
1.30 pm	Tryster Act: A Not So Holy Brunch	Crown & Anchor – Second brunch show. Seating at 1 pm. Tickets exclude food and drinks; $25 minimum spend.
10 pm	Sunday Service / Leather Night	Gifford House, Club Purgatory – Sunday’s leather and gear-themed club listing. The two names in the supplied programme are grouped here pending venue confirmation.

Spooky Bear 2026

• Ursus Men presents Spooky bear, a weekend of costume parties, bear markets, bear bingo, dune tour, tea dances and drag brunch.
• Stay at the Crowne Pointe Historic Inn Adults Only, rated “Excellent” by guests with an outdoor swimming pool, delicious breakfasts and perfect location.

The Main Venues

• Crown & Anchor – 247 Commercial Street. A waterfront entertainment complex with the Paramount nightclub, cabaret, restaurant and smaller bars
• Red Room – 258 Commercial Street, at the Art House. The program switches between ticketed cabaret and late club nights. Possessed expands the Halloween party across several spaces; other shows have their own start times and tickets.
• Tin Pan Alley – 269 Commercial Street. A piano bar, dining room and waterfront patio, useful for a meal and live music between performances.

Where to Go Before the Party

• Shipwreck Lounge – At the Brass Key, 67 Bradford Street. A relaxed cocktail lounge for meeting friends before the night’s costume party. The venue publishes daily opening from 5 pm.
• Walk through Commercial Street between bookings to see the costumes and decorated shopfronts. This is part of the weekend atmosphere, rather than a scheduled Halloween parade.

Getting to Provincetown by Ferry

Bay State Cruise Company operates a reduced late-autumn schedule, with a special Thursday sailing for Halloween weekend:

• Thursday 29th and Friday 30th October: Boston departure at 1 pm, arriving in Provincetown at 2.40 pm.
• Saturday 31st October and Sunday 1st November: Boston departure at 8.30 am, arriving at 10.10 am.
• Return sailings on all four days: Provincetown departure at 3 pm, arriving in Boston at 4.40 pm.
• No ferry is scheduled for Monday 2nd November. baystatecruisecompany.com

The ferry leaves Boston from 200 Seaport Boulevard and arrives at MacMillan Pier, close to central Commercial Street. baystatecruisecompany.com Reserve ahead and check service updates before travelling.