Provincetown Upcoming 2026 Events

Mates Leather Weekend | October 1-5 

Mates Leather Weekend brings the leather community together for a laid-back weekend of socializing and gatherings around town. 

Fall Monumental Yard Sale | October 10-12

The Fall Monumental Yard Sale turns the town into a weekend treasure hunt. Businesses set up curbside and residents hold yard sales, so it is an easy weekend to wander, browse, and find something to bring home before the winter quiet sets in.

Women’s Week | October 12-18 

Women’s Week fills the town with comedy, music, theater, readings, film, and community gatherings, along with dune tours, whale watching, and sports tournaments. The main week runs October 12 through 18, with some events beginning Friday, October 9. This is one of the longest running events of its kind in the Northeast and lodging fills early, so guests should plan well ahead. 

TransWeek | October 18-25 

TransWeek, formerly known as Fantasia Fair, celebrates its 50th year in 2026. The week includes workshops, a fashion show, two formal banquets, and a talent show, and everyone is welcome to take part. It is the longest running event of its kind in the world. 

Spooky Bear | October 29 to November 1 

Spooky Bear closes out October with costume parties, a meet and greet, and Halloween celebrations hosted by the bear community. 

Provincetown Food and Wine Festival | November 4-8

The Provincetown Food and Wine Festival celebrates the town’s restaurants and hospitality with a grand tasting at Town Hall, prix fixe dinners, wine tastings, a drag brunch, and a pie competition. An easy fall weekend for guests who enjoy good food and wine.

New England Leather Weekend | November 20-22

New England Leather Weekend brings the leather community together for a weekend of gatherings, workshops, and the Mr. New England Leather contest.

Annual Lighting of the Pilgrim Monument | November 25

Each year the town gathers to light the Pilgrim Monument for the holidays. The lighting marks the arrival of the Mayflower Pilgrims in Provincetown and brings the community together to welcome the season.

Holly Folly | December 4-6 

Holly Folly is Provincetown’s holiday festival, with open houses, holiday shopping, an inn stroll, gallery events, and dance parties. The kickoff weekend runs December 4 to 6, with more events on weekends through the month.

First Light | December 31 to January 3 

First Light is Provincetown’s New Year celebration, with a holiday market, live entertainment, and the New Year’s Day Polar Bear Plunge in the harbor. A festive way to close out the year by the water.