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Spend a frightfully fun Halloween & Spooky Bear weekend in Ptown October 29 - Nov 1, 2026

A quintessentially ghoulish New England Halloween awaits you as Provincetown hosts a monstrous medley of parties, dances, a haunted house, costume ball and more.

Plan Your Ptown Halloween!

2026 Spooky Bear Halloween Events

Beach Sauna & Cold Plunge

Provincetown’s only beachfront sauna & cold plunge, set directly on the harbor at 333R Commercial Street. Our cedar barrel sauna features a window overlooking the water, boats, and pier. Between rounds of heat, plunge into the healing ocean salt water or our cedar & stainless steel cold plunge tank. Open year-round.
Thursday October 29th
The Yoga Joint
333R Commercial Street Unit 1

Martinis & Mingle Tour

The Martinis & Mingle Tour is an immersive, 90 min social stroll that blends Provincetown’s vibrant cocktail culture with its rich bohemian, maritime, and LGBTQ+ history. Led by local guide Cathy, the tour offers a “sip-and-see” experience down historic Commercial Street, making it a favorite for groups, couples, and solo travelers looking for a lively introduction to the town.  For more info please visit www.ptownwalkingtours.com
Thursday October 29th
4:30 pm

MIXTAPE – James Jackson Jr.

MIXTAPE is your Thursday night soundtrack. Join Broadway’s James Jackson Jr. for an evening of live piano, sing-alongs, and all your favorite songs in the Crown Restaurant & Courtyard. Whether you’re belting out the classics, requesting your go-to anthem, or just enjoying the music with a cocktail, MIXTAPE is the perfect way to spend a […]
Thursday October 29th
9:00 pm – 11:00 pm
Crown & Anchor
247 Commercial Street, Provincetown, MA 02657

FAT SLUT – SPOOKY BEAR

LA drag superstar Meatball is bringing her hit party FAT SLUT to Spooky Bear 2026! Bears know how to party in the fattest and sluttiest way possible. -DRAG SHOWS & SPECIAL GUEST -SEXY GOGO DANCERS -DANCE PARTY -THE ORIGINAL SEXY FOOD EATING COMPETITION
Thursday October 29th
9:00 pm
Crown & Anchor
247 Commercial Street, Provincetown, MA 02657

Beach Sauna & Cold Plunge

Provincetown’s only beachfront sauna & cold plunge, set directly on the harbor at 333R Commercial Street. Our cedar barrel sauna features a window overlooking the water, boats, and pier. Between rounds of heat, plunge into the healing ocean salt water or our cedar & stainless steel cold plunge tank. Open year-round.
Friday October 30th
The Yoga Joint
333R Commercial Street Unit 1
No event found!

Spooky Bear Weekend is produced by the Northeast Ursamen.

Spooky Bear Weekend is produced by the Northeast Ursamen.

Spooky Bear Halloween Weekend Pics

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