One of the most frequent questions asked of “townies” is, “What’s Provincetown like when the throngs of summer visitors begin to subside?” The honest answer is that the transitions between seasons here at the end of Cape Cod are gradual — and beautiful. Sure, the crowds begin to thin after Labor Day. But Provincetown has something to offer visitors and locals alike all throughout the year.
While Provincetown’s community is always tight-knit, visiting during the fall or winter offers the chance to drop into numerous community-oriented events. You’ll get to mix and mingle with the year-rounders, and connect with P-Town’s locals in a new way. And with events like Swim for Life, Mates Leather Weekend, Women’s Week, and Spooky Bear (Provincetown’s annual Halloween celebration), there’s something happening for the full spectrum of the LGBTQ+ community.
Provincetown is here for our LGBTQ+ family throughout the year, no matter the size of your wallet. And planning a trip in the autumn is a great way to stretch those three-dollar bills. Not only will you benefit from greater lodging availability, but you’ll also find less costly overnight rates.
If you’ve been to Provincetown before, a visit in September or October can also reveal familiar spaces through a brand-new lens. P-Town may be known for lush, seaside summers, but rest assured, the famous Cape Cod light, dunes, and strolls through Provincetown take on different colors and qualities at other times of the year.
Visit ptown.org to plan your trip and follow @visitptown on Instagram to catch a glimpse of everything happening in Provincetown right now.
Annual Jockstrap Bike Ride, September 1
The Second Annual Jockstrap Bike Ride, presented by Bike Athletic. Celebrate the unofficial end of summer and arrival of fall with a jockstrap-clad bike ride through the center of town and back to the Provincetown Brewing Co. taproom for a disco dance party.
Labor Day Weekend, September 1-4
While Labor Day Weekend marks the end of the summer season for many, the long weekend is cherished by locals and visitors alike as Provincetown’s second summer. Located 50 miles offshore, P-Town stays warm while the weather inland cools thanks to the tepid ocean waters surrounding it.
Swim for Life, September 8-10
This quintessential Provincetown event and fundraiser has raised $6 million since 1988 for HIV causes, women’s health, and the LGBTQ+ community. Join swimmers, volunteers, kayakers, and cheerleaders from across the country for this high-spirited weekend. Take the plunge!
National Gay Pilots Association Cape Cod Classic, September 14-17
From humble beginnings over 30 years ago, the Cape Cod Classic has grown to become the National Gay Pilots Association’s flagship East Coast event. This beautiful and intimate setting provides the perfect backdrop to catch up with old friends, meet new ones, and bond over a common love of aviation.
Tennessee Williams Theater Festival, September 21-23
Adventure-seeking audiences voyaging to Provincetown will thrill to performances of plays and dramatic short stories by Tennessee Williams that feature spaceships, aliens, vampires, ghosts, and bizarre imaginary worlds. From his teenage years to the months before he died, Williams wrote science fiction and fantasy to boldly explore his fears and hopes for the future.
Mates Leather Weekend, September 28-October 2
For those into the leather scene, Mates offers a kick-back, have-a-good-time, meet-some-hot-new-friends weekend for those who want to hang out, socialize, relax, or party with other like-minded people in leather, rubber, and uniforms.
Washashore Music Festival, October 6-8
The Washashore Festival is an unforgettable, multi-venue, genre-bending queer music festival. Come celebrate the freedom, breadth, and power of queer expression in this village at the end of the world that has long been a safe haven for rebels, adventurers, artists, and liberated souls of all stripes.
Women’s Week, October 9-15
Whether it’s getting to see the best performers and comics in LGBTQ+ culture today, walking down Commercial Street holding hands with the woman in your life, or basking in the sunlight and taking in the natural beauty of Provincetown, there is no festival on the planet that celebrates women like Women’s Week.
Monumental Sale, October 6-8
As the weather cools, many of Provincetown’s businesses and homeowners take this opportunity to empty out those closets and storage rooms to host a town-wide sale. Visit ptown.org for the full list of participating stores and addresses.
TransWeek, October 15-22
Part learning experience, part social gathering, and part reunion, TransWeek is a full immersion experience, meaning attendees can and usually do spend an entire week presenting their gender as they wish.
Spooky Bear Weekend, October 27-29
Hosted by the Northeast Ursamen and the Crown & Anchor, this quintessentially ghoulish New England Halloween experience awaits you as Provincetown hosts a monstrous medley of parties, dances, a haunted house, costume ball, and more.
Holiday Season Preview
The fun in Provincetown continues well into November with events like the Provincetown Food + Wine Festival, Mr. New England Leather, Thanksgiving, Pink Friday, and then Holly Folly and First Light as the holiday season approaches in December.