Insiders know that fall is the best time of year to visit Provincetown, a picture-perfect New England resort town known for its dramatic light, extraordinary beaches, and all things LGBTQ+. From classic queer events and arts festivals to a brand new food and wine festival, Provincetown’s legendary “Second Summer” is the ideal time to visit.

ArtProvincetown Festival, October 8-10, 2021

The first annual ArtProvincetown Festival will include museums, galleries, studios and a marketplace for artists and craftsmen. Aimed at artists, collectors, designers, and fans of the arts in all forms, the Festival will feature receptions and parties with special hosts. The mission of the ArtProvincetown Festival is to highlight the diverse and beautiful art that Ptown has to offer. Note that the Washashore Music & Arts Festival is happening the same weekend and will have crossover events.  

Washashore Music & Arts Festival, October 8-10, 2021

The Washashore Music & Arts Festival is an annual gathering celebrating the union of live music, queer artists, good beer, and the everlasting singularity of Provincetown. People who attend Washashore Festival will be compelled to participate in Provincetown Brewing Co.’s commitment to #draftivism: giving back to progressive causes while having a good time. Events will be held at Provincetown Brewing Co., Crown & Anchor, Red Room (formerly Velvet Lounge), and other venues. The event is presented by Provincetown Brewing Co. and executive produced by Live from Provincetown and NYA Presents.

Monumental Yard Sale, October 9-11, 2021

Shopping in Ptown hits an all-time high during the annual Monumental Yard Sale Weekend, which will be held on Indigenous Peoples Weekend, October 9-11, 2021. Each year, town residents, as well as retail shops, participate in the unusual sale where visitors can find one-of-kind treasures lining the sidewalks and yards all over town. It’s also a great time to begin holiday shopping at Ptown’s incredible independently-owned boutiques that offer home goods, clothing, jewelry, crafts and antiques, as well as more than 50 galleries displaying fine art, here in America’s oldest continuous art colony.

Women’s Week October 11-17, 2021

With over 150 events for women, including music, comedy, dance parties, film screenings, dune tours, sails, food events, sports events, and more, Women’s Week once again brings thousands of women together—singles and couples alike. Every year there is the Community Dinner, which features performances.

Single Women’s Weekend October 13-16, 2021

The annual Single Women’s Weekend, postponed from May, is now scheduled for October. It’s designed to be a fast, fun way for single lesbians to meet other single lesbians – live and in person. Registration includes Friday’s Meet & Greet, Friday’s Speed Dating and Saturday’s Toys of Eros Workshop.

Fantasia Fair, October 17-24, 2021

Since 1975, Fantasia Fair (a.k.a. Fan Fair) has been acclaimed as the original transgender event. It offers anyone who identifies as trans (and even those who don’t) a place to gather. Daily keynote speakers and workshops are a big part of the week-long schedule. There are also fashion shows, formal banquets, lunches, and a cabaret/talent show. It’s an immersive, week-long event, the longest-running transgender event in the world.

Halloween Weekend October 29-31, 2021

One of the biggest events in October, Halloween is the best night of the year to don costumes and play on Commercial Street. Expect flash mobs, performances, and lots of parties. Halloween also overlaps with Spooky Bear Weekend. which includes themed parties, shows and a farewell brunch.  

Provincetown Food & Wine Festival, November 4-7, 2021

The new festival, created to celebrate local chefs and restaurants is planned to be an annual event. The schedule includes a Tuscan Wine Tasting & Seminar, Afternoon Tasting & Social, Italian Fine Wine Dinner, Amalfi Coast Wine Dinner, Celebrating Women, GRAND Tasting and Champagne Drag Brunch. Participating restaurants and hotels include Strangers & Saints, The Crown & Anchor, Pilgrim House, Masthead Resort & Cottages, Provincetown Brewing Company, Café Heaven, Tin Pan Alley, Post Office Café and Cabaret, and Perry’s Fine Wine & Liquors. Details at Provincetown Food & Wine Festival.

For more on fall in Provincetown, visit Provincetown Tourism.

About the Author

Bryen Dunn is a freelance journalist based in Toronto with a focus on tourism, lifestyle, entertainment and community issues. He has written several travel articles and has an extensive portfolio of celebrity interviews with musicians, actors and other public personalities. He’s willing to take on any assignments of interest, attend parties with free booze, listen to rants, and travel the world in search of the great unknown. He’s eager to discover the new, remember the past, and look into the future.