How to Enjoy Provincetown All Year Long

Sponsored by the Provincetown Office of Tourism

As with any seaside destination, the social scene heats up in Provincetown, Massachusetts, when the summer sun shines bright and some of the year’s biggest theme weeks and community parties come to town. But in truth, Ptown never really cools down thanks to an eclectic lineup of events that provides plenty of reasons to frequent the Outer Cape throughout the year.

From Pride in late spring to December’s Holly Folly, the streets of Ptown are always percolating with locals and visitors coming together for a good time and great memories. Plan your visit accordingly with Ptown’s most engaging events and joyful theme weeks, rounded up below.

May/June

Twenty Summers is an art incubator meant to imagine what a more sustainable Provincetown would look like 20 summers from now. Starting in mid-May and continuing through mid-June, this forward-looking nonprofit hosts discussions, concerts, and special events in the restored Hawthorne Barn in Ptown’s East End.

Also in mid-May, Single Women’s Weekend (May 17-19) invites attendees to step away from their dating apps and usual pickup spots in favor of a weekend of mixers, speed dating, and fun activities like a Cape Cod National Seashore dune tour.

A four-day gathering of queer women, trans-, nonbinary, and gender-fluid people kicks off May 30 with the return of the Womxn of Color Weekend. The event schedule is pure Ptown, with activities including whale watching, sunrise yoga, pool parties, small-group dinners, and lots of nightlife.

Adding to the excitement that same weekend is Provincetown Pride (May 31-June 2), which features a Pride festival and rally at Provincetown Town Hall, the Queer Comedy Showcase, a 5K run/walk, and a variety of shows that keep the town’s bars, restaurants, and nightlife venues hopping.

The Provincetown International Film Festival (June 12-16) packs a big cinematic punch with its 80-plus American and international independent feature and short films. The festival’s annual Filmmaker on the Edge award also brings in boldface names such as Sofia Coppola, Ang Lee, and Call My by Your Name director Luca Guadagnino, all past honorees.

“The Olympic Gaymes” is the playful theme for this year’s Frolic Weekend (June 13-17), a celebration catering to queer and trans men of color from around the world — and it will take true athletic ability to keep up with all the events on offer. More than 15 parties and activities are scheduled for the weekend, ranging from the Tea Dance and the Locker Room Dance Party at the Boatslip, to an homage to the documentary Paris Is Burning (and also to the host city for this year’s actual Summer Olympics) with a Closing Ceremony Dance Party at the Crown & Anchor.

The ProvincetownPortuguese Festival (June 28-30) is an annual reminder of Ptown’s roots as a Portuguese fishing village at the end of the world…or at least the end of Cape Cod. Witness the blessing of the fleet, enjoy the crafts fair and live music (plus a food tent — hello, malassadas and caldo verde!) on Ryder Street’s Portuguese Square, and get a real taste of Provincetown’s culinary and cultural scene.

July/August

Throughout July and August, Great Music on Sundays @ 5 draws crowds to the Unitarian Universalist Meeting House of Provincetown for a variety of Sunday afternoon musical performances. Among the highlights this year: Broadway showtunes, a cappella music, and classical masterpieces by Beethoven and Haydn.

The largest annual gathering of LGBTQ+ families in the world, Family Week (July 27-Aug. 3) is a terrific opportunity for parents, children, and extended families to reconnect and enjoy a robust program of activities, including youth-only events.

Don’t miss out on the 46th annual Provincetown Carnival (Aug. 17-24), which sports a “Renaissance X Revolution” theme this year. Tens of thousands of visitors are expected for the weeklong jamboree of creativity, costumes, and parties. At Thursday’s big parade, keep your eyes peeled for the final float, which reveals the theme for 2025. After all, the pros start plotting their costume one year in advance (we kid…somewhat!).

September/October

As the air turns crisp with autumn, Provincetown shifts into literary mode with the Provincetown Book Festival (Sept. 20-22). This lively gathering of book lovers and writers features author meet-and-greets, readings, and discussions in a town that has inspired great works by Tennessee Williams, Norman Mailer, Michael Cunningham, and Mary Oliver, just to name a few.

Speaking of Williams, the Provincetown Tennessee Williams Theater Festival (Sept. 26-29) is a long weekend of performances of the famed playwright’s classics and more experimental works in his former summertime haunt (it’s in Ptown that he’s said to have worked on The Glass Menagerie and A Streetcar Named Desire).

Explore Ptown at the more relaxed pace of its shoulder season with Women’s Week (Oct. 14-20; related events begin Oct. 11). Now celebrating its 40th year, it packs in hundreds of things to do—from wine and spirits tastings and sailing on the bay to meditation classes and feminist readings.

November/December

There’s still plenty cooking in Ptown toward the end of the year, including the Provincetown Food & Wine Festival (Nov. 7-10). At this who’s who of the Cape Cod culinary world, oyster tastings, wine tastings, themed dinners, and fireside cocktails happen almost round the clock—so if you leave hungry on Sunday, it’s your own fault!

Find one-of-a-kind gifts for everyone on your list — and have a ball along the way — at Holly Folly (Dec. 6-8). Started as a way for members of the LGBTQ+ community to enjoy the holidays with their chosen family, Holly Folly continues to honor its roots while growing into a multiday celebration of performances, shopping experiences, and delicious offerings from local restaurants. It’s the only place where you can enjoy glühwein and ornament-shopping at a Bavarian-style Christmas market mere steps from a walk-up counter for lobster rolls. Now, that’s one-stop holiday shopping.