The Underwear Party: Spooky Bear 26 Edition

Community Focused

Shipwreck Lounge

A spooky weekend getaway in Provincetown featuring Adam Berry, running October 9–12, 2026. This haunting adventure combines accommodation at the Brass Key Guesthouse with special programming and events designed to make your fall escape unforgettable. Perfect for those looking to celebrate Halloween season in one of the Northeast's most vibrant queer destinations.

Tea Dance

Boatslip Resort & Beach Club

Broadway

Post Office Cafe & Cabaret

Four years in, this Provincetown drag spectacular is still one of the most fun nights on the Post Office stage. Delta Miles, Qya Cristál, and Roxy Pops deliver live vocals, three-part harmonies, quick-change costumes, and comedy that lands, running through hits from Lady Marmalade and Respect to Broadway favorites like Over the Rainbow and the Moulin Rouge Diamonds Medley. Whether it's your first time or your fifth, expect big voices, bigger laughs, and classic Ptown glamour.

Comedy

Red Room

Poppy Champlin is a Rhode Island Comedy Hall of Fame inductee and Ladies of Laughter 2024 winner who's logged serious time on Showtime, Oprah, and Joan Rivers. Her observational comedy tackles tough subjects with the kind of fearless humor that makes you laugh at life's most formidable moments. She's a regular in Provincetown and a producer of The Queer Qomedy Queens tour, now in its twelfth year. Expect stand-up that's sharp, character-driven, and genuinely funny.

Cabaret

Post Office Cafe & Cabaret

A deliriously campy mashup that crashes The Golden Girls into Mean Girls—complete with Cady Heron waking up in a Miami High fever dream where Dorothy, Blanche, Rose, and Sophia have become The Plastics. Expect shade, schemes, senior-discount savagery, and the kind of clever character parodies that make you wonder why nobody thought of this sooner. Fast-paced, funny, and exactly the kind of theatrical chaos Provincetown does best.

Drag Brunch

The Crown & Anchor

Saturday mornings in Provincetown just got a whole lot more fabulous. Crown Jewels is an all-singing, all-dancing drag brunch starring Delta Miles, Roxy Pops, and Qya Cristal — expect powerhouse vocals, dazzling performances, and plenty of laughs while you brunch in the restaurant and courtyard. Doors open at 10:30 AM, show starts at 11:00 AM. Note: ticket doesn't include food or drinks, but there's a $25 minimum spend.