Home » Provincetown Events to Enjoy This Fall and Winter!

Provincetown Events to Enjoy This Fall and Winter!

by Lauren Mulvey
Provincetown Events (Photo by Carlos Barquero)

A thrilling time can also be found in this queer haven at the tip of Cape Cod during the fall and winter months, making P'town a year-round destination for LGBTQ+ travelers.

Provincetown may be famous for summertime shenanigans, but a thrilling time can also be found in this queer haven at the tip of Cape Cod during the fall and winter months, making the town a year-round destination for LGBTQ+ travelers.

P’town’s schedule is jammed packed with events and theme weeks almost every week until the New Year. As the leaves drop off the trees, prices on accommodations will do the same, and special holiday shows and events, along with memorable dining experiences and a chance to explore the town at a slower pace. Here’s what’s on the docket for the upcoming months. 


Washashore Queer Music Festival October 7 – 8 

Jam out in Provincetown with this genre-bending, Queer music festival that seeks to celebrate freedom and the power of queer expression. This year’s lineup includes Jake Wesley Rogers, Boyfriend, Superknova, Drizzy Bravo and more. The festival will be hosted by actor, playwright, songwriter and director, John Cameron Mitchell.


Women’s Week in Provincetown (Photo by Mavo)

Women’s Week October 9 – 15 

Celebrate Women’s Week this year with parties, performances, special guests, shows, films, and literary talks, with a total of 300 events from which to choose. Some musicians to expect are Melissa Ferrick, BETTY, Zoe Lewis and Lucy Wainright, and comedians will include Mimi Gonzalez, Kristen Becker and Judy Gold and more.

TransWeek October 15 – 22

P’town is proud to host the “original” TransWeek which includes brunches, workshops, a banquet and dance party, keynote speakers, a film festival, meet and greets, and more. Attendees are invited to learn special skills through workshops, make new friends, watch queer and trans-centric films, and feel free to be themselves in Provincetown.

Celebrate Halloween in Provincetown 

Perhaps one of the best times visit to Provincetown would be to celebrate Halloween, when the town puts its artistic chops and creative legacy on full display with elaborate costumes, entertainmen, and good ole Halloween cheer. P’town’s biggest Hallow’s Eve event is Spooky Bear, which features costume balls, a Bear-Mart, and Halloween events and performances at various local venues like Tammie Brown’s, Red hook, and Crown & Anchor. And don’t miss the new “Haunted Masquerade Ball” at Gifford House, Possessed III Halloween & Costume Party at Red Room, and Bianca del Rio at Town Hall.



Provincetown Food & Wine Festival – November 2-5 

This year’s food and wine festival has a wine dinner, a galley sip and stroll, a cookbook signing, tea dance, and it wouldn’t be complete without a big gay boozy brunch. Stop by to indulge in local foods paired with global wines and practice those sommelier skills. 


New England Leather Weekend (Photo by ESB Professional)

New England Leather Weekend – November 17 -19 

Could you be the next Mr. New England Leather? To see if you’ve got what it takes, attend this year’s festival at the Crown & Anchor for all things leather gear. This is the perfect opportunity to show off that new leather jacket or tight leather pants you’ve got in the back of your closet and mingle with visitors and P’town locals. 

Pink Friday – November 24

Forget ‘Black Friday’ because the day after Thanksgiving in P’town is all pink. Visit “mom & mom” or “pop & pop” owned shops that make Provincetown’s retail scene so lively. The Canteen Holiday Market, opens on Pink Friday and transforms into a Austrian chalet adjoining a marketplace pop-up that’s perfect for socializing, enjoying holiday refreshments, and shopping for handcrafted goods made by local artisans.

Lobster Pot Christmas Tree – November 16 

This is your chance for a quintessential P’town photo op when the annual Christmas tree is put up in Lopes Square. This isn’t any ordinary Christmas tree, but 120+ lobster pots stacked over two stories high, and outfitted with ribbons, garlands, and thousands of festive lights to create probably one of the most unique coastal Christmas tree traditions on the east coast. 


Holly Folly (Photo by Trevor Pittinger)


Holly Folly December 1-3 

It’s a quick shift to holiday celebrations with Holly Folly, a 3-day festival full of entertainment, food, holiday shopping, open galleries, and innkeeper open houses. And don’t forget to partake in some of Provincetown’s nightlife. This year the Boston Gay Men’s Chorus is back in town with a new show: Green & Gleeful on December 2. 

 “After a few years away, we are thrilled to return to P’town during Holly Folly, help support the small businesses and local economy in town, and showcase the wonderful talented voices of the BGMC,” said Sarah Shoffner, Boston Gay Men’s Chorus Executive Director. “The 350+ members of the chorus are excited to share their lives through music with a fabulous dose of holiday flare.”


Well-Strung (Photo by Mark Cortale)

First Light New Year’s WeekendDecember 29 – January 1 

Celebrate the end of 2023 and ring in the New Year in Provincetown with fine dining, fireworks, and the New Year’s Day tradition of the Polar Plunge. Enjoy a glass of champagne at one of the many harborside restaurants while watching the fireworks at MacMillan Pier sparkle over the bay. Enjoy the NYC-based singing string quartet Well-Strung in ‘A Holiday Reunion’ at Town Hall on Saturday, December 30. The string quartet, with a modern twist, plays universally recognized classical pieces while singing hits from Dolly Parton to Rihanna to Taylor Swift for a uniquely engaging holiday experience.

Dance into the final hours of 2023 at the A-House or The Gifford House’s full-space New Year’s Eve takeover, then welcome 2024 on January 1 by jumping into the Provincetown Harbor at the Provincetown Polar Bear Plunge, a fundraiser for The Center for Coastal Studies. Warm up post-plunge with a celebratory cocktail at Harbor Lounge.

For tickets and the complete fall and winter schedule of LGBTQ+ events in Provincetown, visit ptown.org/calendars.

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