Name: Jackie & Jan's Y2J
Start: 2026-09-06T19:00:00-04:00
Location: Red Room

Provincetown has been a refuge and creative haven for LGBTQ+ people for decades — the kind of place where you can walk down the street and feel genuinely seen, where the community isn't performing for anyone else's comfort. The whole town has this relaxed, anything-goes energy that comes from generations of queer people building something real here, not just a tourist attraction but an actual home where you can be exactly who you are.

The scene here spans everything from the Boatslip Resort's legendary afternoon tea dances on the beach to drag shows at The Crown & Anchor that pack the room with locals and visitors who actually know how to have fun. You've got the Post Office Cafe & Cabaret for cabaret nights, the Red Room for dancing, and smaller spots like Gifford House where the vibe is more about community than spectacle — which is exactly the point, emphasized by the various theme weeks throughout the year, like Bear Week, Frolic, Women's Week, Baby Dyke, Carnival, and Spooky Bear.

Provincetown

Piano Bar Lily May Harrington

Piano Bar Ben Morren

A Woman Named Carlös The New Classic

Underwear Night

Dyke Drag Brunch Women's Week

Dyke Drag Brunch

Solid Gold Tea

Piano Bar James Jackson Jr.

Sunday Service

Ecstatic Dance with Patricia van Dijkhuizen & Woof Woof Meow

Piano Bar with Lily Mae Harrington

Wilde Salsa Class

Piano Bar Peter & Hilarie

Piano Bar Tori & Chris

Club Fag Bash

Diva!: Mess Becomes Her

Piano Bar with Britanny & Clint

Club Himbo (Jockstrap)

Dog Tag Tea

Movie Night Double Feature in the Wilde

Spookey Helltown Burlesque

Tori McLean & Chris Grasso

Club Disco Night

Crown Ghouls: Drag Brunch 10:30AM Spooky Bear

Crown Ghouls: Drag Brunch 1PM Spooky Bear

Boatslip Tea Dance

Heated Rival Tea

Destroy Mona

Piano Bar with Lily May Harrington

Club Underwear Party

Club Leather Night

Goodnight Provincetown

Club Latin Night

Purgatory Drawing Class

Marti Gould Cummings in Stranger Queen

Solid Gold Tea Spooky Bear Weekend

TransWeek, also known as Fantasia Fair, is a week-long gathering held in Provincetown, Massachusetts for transgender and gender-diverse people. It offers workshops, keynote speakers, meals, entertainment, and social events such as a fashion show, open mic night, follies performance, and a bingo festival. The event includes an opening welcome reception, dinners, dances, and an awards banquet across its schedule.

A week-long transgender community gathering in Provincetown, MA.

TransWeek 2026

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.

A New England Halloween weekend in Provincetown with parties, dances, and Spooky Bear events.

Spooky Bear Weekend

Holly Folly is Provincetown's LGBTQ+ holiday celebration, described on the page as the nation's largest and oldest such event, first held in 1997. It brings the queer community together to celebrate the holiday season with events including performance art, fine dining, and holiday shopping along Commercial Street. The 2026 celebration kicks off with a weekend December 4-6, with expanded Holly Folly weekends throughout the month.

Provincetown's LGBTQ+ holiday celebration featuring shows, shopping, and festive events.

Holly Folly 2026

Two of RuPaul's Drag Race's sharpest queens are bringing their all-live-singing Y2K spectacular to P'town. Jackie Cox and Jan Sport belt out your favorite late-90s and early-2000s pop anthems—Britney to Backstreet—while serving chaotic comedy, TRL-worthy looks, and enough rhinestones to crash a Dell desktop. It's a high-energy nostalgia trip that asks the essential question: what if the Y2K bug never actually disappeared? Door opens at 6:45 PM.

Jackie & Jan's Y2J

Pop Music & Divas

Drag Culture

On Sunday, September 6th at 7:00 PM, Two of RuPaul's Drag Race's sharpest queens are bringing their all-live-singing Y2K spectacular to P'town. Jackie Cox

Two of RuPaul's Drag Race's sharpest queens are bringing their all-live-singing Y2K spectacular to P'town. Jackie Cox and Jan Sport belt out your favorite

Jackie & Jan's Y2J at Red Room

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Two of RuPaul's Drag Race's sharpest queens are bringing their all-live-singing Y2K spectacular to P'town. Jackie Cox and Jan Sport belt out your favorite late-...

Jackie Cox

Jan Sport

Jackie & Jan's Y2J – Sep 6, 2026 – Red Room | Provincetown | Gathry

Cabaret

Drag Shows

Live Entertainment

Performance Venue

pop music

RuPaul's Drag Race

Discover Provincetown's premier destination for intimate live entertainment at the Red Room on Commercial Street. The vibrant stage hosts an eclectic mix of top-tier comedy, captivating cabaret, live music, and bold performance art. Immerse yourself in the heart of P'town's creative scene for an unforgettable night out in a uniquely welcoming atmosphere.

Jackie & Jan's Y2J

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Coming Up in Provincetown: TransWeek 2026