Tuesday, April 16, 2024
CitiesDestinationsEventsHoliday TravelWinter Travel

Provincetown: Don Your Gay Apparel for These 4 Fun Holiday Weekends

As the mercury on the thermometer dips and the wind in the air gets cooler and crisp, most travelers are on the prowl to find a warm-weather destination for their next trip. Don’t count out the Northeast U.S., specifically Provincetown, Massachusetts as an option. It’s the go-to destination for fun summer events, such as Bear Week or Girl Splash, but the last few months of the year are jam-packed with several LGBTQ+ events, including Fantasia Fair, touted as ‘the longest-annual event in the transgender world.’ 

If you’re looking for a fun fall or winter weekend getaway, consider a trip to Ptown. Join festive revelers as they converge on the quaint coastal town during the holidays – Halloween, Thanksgiving, Christmas, and New Year’s – and watch the streets come alive with a robust line-up of queer-friendly events. 

Spooky Bear Weekend (Photo Credit: The Provincetown Office of Tourism)
Spooky Bear (Photo Credit: The Provincetown Office of Tourism)

Halloween Weekend (Oct. 28-31)
Halloween is not only a special time for ghosts, goblins, and things that go bump in the night. In Provincetown, the spine-tingling holiday gives us another reason to don a fabulous costume or queer couture to show off your own spooky flair. During Halloween weekend, October 28-31, Provincetown venues host scary movie-themed tea dances at Boatslip, a dance party and costume contest at Red Room, Halloween dinners, live entertainment, drag brunches, and more! 

Spooky Bear Weekend (Photo Credit: Northeast Ursamen | Crown & Anchor)
Spooky Bear Weekend (Photo Credit: Northeast Ursamen | Crown & Anchor)

The annual Spooky Bear Weekend is always a popular draw for furry men and their admirers. And this year will be no different, with its hair-raising theme, Spooky Bear: American Hairy Story. During the day, consider taking a creepy ghost tour of historically haunted Ptown, head to the Crown & Anchor to win prizes at a trivia competition, take a leisurely stroll around the Bear-Mart on the Boatslip, or watch the sun go down with Art’s Dune Tours. You’re guaranteed to have a spooktacular time. 

Canteen Holiday Market in Provincetown (Photo Credit: Polar Bear Plunge in Provincetown, Massachusetts (Photo Credit: Provincetown Business Guild)
Canteen Holiday Market in Provincetown (Photo Credit: Provincetown Business Guild)

Thanksgiving Weekend (Nov. 25-28)
During the last full week in November, Provincetown’s season of lights begins when the Pilgrim Monument lights up the sky, commemorating the Pilgrims’ first landing in the New World. Before overindulging in a Thanksgiving feast, you can get your steps in at the annual Provincetown Pilgrim 5K Trot, a fundraiser for Helping Our Women (HOW). A $100 prize is awarded to the 1st female and male to cross the finish line. Afterward, enjoy a traditional Thanksgiving dinner – or one with a modern twist – at one of many restaurants open for the holiday, such as Mews, Napis, The Pointe, Red Inn, Strangers & Saints, or Tin Pan Alley.

Drag Bingo (Photo Credit: Provincetown Business Guild)
Drag Bingo (Photo Credit: Provincetown Business Guild)

Enjoy the day after Thanksgiving at your leisure. If you need to burn off turkey-day calories, walk through Canteen’s Holiday Market in search of that perfect holiday gift and support local businesses or keep the merriment going with festive food and beverages. Try your luck at the annual Day After Christmas Drag Bingo with Thirsty Burlington at the Crown & Anchor. Don’t forget to snap an Instagram-worthy pic in front of the Lobster Pot Christmas tree in Lopes Square.

Jingle Bell Run (Photo Credit: Provincetown Business Guild)
Jingle Bell Run (Photo Credit: Provincetown Business Guild)

LGBTQ Holiday Festival Weekend (Dec. 3-6)
The annual LGBTQ Holiday Festival, usually held the first weekend in December, is a three-day festival that welcomes the winter season with entertainment, food, shopping, nightlife, and merry events. Take a stroll down Commercial Street for the Holly Folly Shop, Hop, and Gallery Stroll to take advantage of the end-of-the-season sales offered at local boutiques. Afterward, put on your ugly sweater and wig for the Jolly Holly Folly Ugly Sweater and Wig Bar Crawl, check out the Pilgrim House Christmas Show, listen to live piano music, and dance the night away at The Vault or A-House – don’t miss their annual Snow Ball. 

Holly Folly Follies Holiday Extravaganza (Photo Credit: Provincetown Business Guild)
Holly Folly Follies Holiday Extravaganza (Photo Credit: Provincetown Business Guild)

On Saturday, express yourself and dress up in a creative, colorful way to celebrate you and the holidays for Holly Folly Express Yourself Day. Locals and out-of-towners don their gay – or however you identify – apparel and dress up as Santa, Rudolph, or a naughty elf for the Jingle Bell Run. Dash down Commercial Street for cheers, prizes, and a champagne brunch at the Crown & Anchor. On Sunday, don’t miss Sunday Service Drag Brunch at Pilgrim House and Holly Folly Follies Holiday Extravaganza, the gayest holiday show in town. 

Polar Bear Plunge (Photo Credit: Provincetown Business Guild)
Polar Bear Plunge (Photo Credit: Provincetown Business Guild)

New Year’s Weekend (Dec. 30 – Jan. 2)
You and your chosen family can ring in the New Year with fireworks, dance parties, drag bingo, a grand New Year’s dinner at The Pointe Restaurant, live performances, and the annual Polar Bear Plunge. Brave the cold waters of the Atlantic Ocean to start the New Year off frigid, fresh, but rejuvenated to take on the year ahead.

Get more information about Provincetown’s upcoming events. Check out their LGBTQ events calendar

Vacationer Staff

Vacationer Magazine's writing staff works hard to bring you all the latest LGBTQ travel articles to help inspire and inform.

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