8 Reasons to Fall in Love with Provincetown This Autumn

Sunday October 3, 2021
Originally published on September 28, 2021

8 Reasons to Fall in Love with Provincetown This Autumn
  (Source:Provincetown Tourism)

Sure, the dip in temperature might require clothing at The Boatslip's infamous tea dance rather than a sunset frolic in nothing but your swim briefs, but for those in the know, fall is one of the best times of year to visit Provincetown. Here's our shortlist of what not to miss:

ArtProvincetown Festival

October 8-10, 2021

Just when you thought there wasn't room in P-Town's packed event calendar, organizers have come together to plan the first annual ArtProvincetown Festival, which will include museums, galleries, studios and a marketplace for artisans. Aimed at artists, collectors, designers, and fans of the arts in all forms, the Festival will feature receptions and parties with special hosts. 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 celebrates the union of live music, queer artists, good beer, and the everlasting singularity of Provincetown. Attendees are encouraged to participate in Provincetown Brewing Co.'s commitment to #draftivism by 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 Art Sale
Monumental Art Sale  (Source: Provincetown Tourism)

Monumental Yard Sale
October 9-11, 2021

Whether you're looking for a new piece of art, gifts for the holidays or a splurge for yourself, there's no better time than P-Town's annual Monumental Yard Sale Weekend, which will be held on Indigenous Peoples Weekend, October 9-11, 2021. Each year, town residents and retail shops participate in the unusual sale where visitors can find one-of-kind treasures lining the sidewalks and yards all over town. Known as America's oldest continuous art colony, you're likely to find curated picks among the 50 art galleries around town.

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.

Single Women's Weekend
October 13-16, 2021

Overlapping with Women's Week is the annual Single Women's Weekend (postponed from May). 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 and Speed Dating and Saturday's Toys of Eros Workshop.

(Source: Provincetown Tourism)

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 and the longest-running transgender event in the world.

[READ MORE: Inside Provincetown's Legacy of Transgender Representation]

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.