As the seaside frost settles into Provincetown, there’s no shortage of opportunities to heat things up with a holiday visit to this beloved
+ coastal community. The days may be shorter, but with so many of P-Town’s guest houses featuring adorable rooms with fireplaces and cozy nooks (often at reduced rates from summer!), a winter trip is the perfect excuse to cuddle up with your favorite person.
The holidays offer a truly unique opportunity to escape to Provincetown with our families — both born into and found. Come gather around a candlelit table for a harborside meal and then spill out onto Commercial Street to enjoy one of the year-long cabarets or club parties. Visit
to learn more about planning your next trip to Provincetown.
Provincetown Food & Wine Festival, November 2-5
This year’s theme is Local Food for Global Wines. In its third year, this fast-growing new festival is highlighting regional bounty from land and sea and promises to keep you swilling and swallowing to your heart’s content.
New England Leather Weekend, November 17-19
Show off your gear, mingle with the friendly members of the leather community, and witness the crowning of the next Mr. New England Leather. With a full itinerary of official events, including the annual beer blast at Provincetown Brewing Co. and the NEL pageant at the Crown & Anchor, this weekend is a perfect opportunity to ship out and suit up.
Lighting of the Pilgrim Monument, November 11
Commemorate the Mayflower’s first landfall in the New World in 1620 with the annual lighting at the Pilgrim Monument Provincetown Museum. The monument is popular all year, but its holiday glow signifies the time the pilgrims spent on the Outer Cape before sailing on to what is now Plymouth.
Lighting of the Lobster Pot Christmas Tree, November 16
Celebrate Provincetown’s heritage as a fishing community as the whole town packs into Lopes Square to light up over 120 seasonally festooned lobster traps. Originally mounted by artist Julian Popko in 2004, the holiday installation has brought cheer to the harbor for nearly 20 years and makes the perfect pilgrimage.
Pink Friday, November 23
A local spin on Black Friday, Pink Friday highlights the wide range of mom-and-mom or pop-and-pop shops that pack Provincetown with one-of-a-kind gift offerings. This holiday season, support P-Town’s pink businesses by visiting in person or shopping online.
Canteen’s Annual Holiday Market, November 23-December 30
From Thanksgiving until New Year’s Day, the Canteen fully transforms into a magical Austrian chalet adjoining a marketplace pop-up perfect for enjoying holiday foods and drinks and buying handcrafted goods from local artisans. Make sure to pop on over to the courtyard at the Crown & Anchor for additional artisans, local goodies, and wine and wassailing galore!
World AIDS Day, December 1
The AIDS Support Group of Cape Cod is holding its 40th anniversary commemoration honoring Provincetown’s historic response to the AIDS epidemic. The candlelight vigil will be held at the Provincetown AIDS Memorial on the town hall’s east lawn.
Holly Folly Weekend, December 1-3
Holly Folly began in 1997 as a holiday celebration among LGBTQ+ chosen family. This year, festivities include holiday performances all over town. Enjoy a Christmas concert with Mike Flanagan, the Jingle Bell Fun Run down Commercial Street, and a walking tour of historic houses. There are two centerpiece town hall shows: the Provincetown Holly Folly Follies produced by Crown & Anchor on December 1, followed by Green & Gleeful, the Boston Gay Men’s Chorus performance on December 2.
Townie Holiday Extravaganza, December 15-17
The Provincetown Theater’s Townie Holiday Extravaganza production includes approximately two dozen performers in a full-scale celebratory yuletide spectacular.
Christmas in Provincetown, December 25
First Light — New Year’s Weekend, December 29-January 1
Ring in the New Year with new and old friends in Provincetown. Enjoy a glass of champagne at a harborside restaurant. Watch the fireworks at MacMillan Pier. Listen to the Well-Strung string quartet perform at town hall on December 30. Dance the night away at A-House or at the Gifford House. Then jump headfirst into the new year at the Polar Bear Plunge, a fundraiser for the Center for Coastal Studies where hundreds splash into Provincetown Harbor. Warm up afterward with a celebratory cocktail at Harbor Lounge.