Provincetown Events 2023: A Cheerful Holiday Season with Lights and Festivities

With the early November ceremonial lighting of the Pilgrim Monument – its 252-foot high tower glows every evening with holiday lights, like a massive Christmas tree overlooking the harbor – the holiday season officially gets underway in Provincetown. As the birthplace of the first Thanksgiving after the Pilgrims landed on the outer Cape over 400 years ago, our holiday heritage is well-established, a time of year when holiday-themed Provincetown events make the season extra special and joyous.

When you stay at our Provincetown bed and breakfast, you’ll be within walking distance of all the festively fun and endlessly entertaining holiday happenings between Thanksgiving and the New Year.

Ice skating in Provincetown

Lighting the Lobster Pot Tree, A Charming Holiday Market, and Shopping Local for Your Gifts

The holiday cheer starts flowing on Thanksgiving weekend, beginning with the annual lighting of the iconic Lobster Pot Christmas Tree in Lopes Square. Constructed out of stacked lobster traps, wrapped with bright red bows, and topped with buoys to complete the classic nautical theme, it’s a “tree” unlike any other you’ll see and honors the generations of lobster-fishing families that have long formed the bedrock of the P-Town community. Join the festivities at the square right by MacMillan Pier at 5:30 pm on Nov 25th, 2023, for the lighting ceremony, and follow it up by grabbing a lobster roll at Mac’s Fish House – one of our favorite Provincetown local restaurants, where the lobster is among the best on the Cape.

That same weekend, skip the generic big-box store Black Friday sales and shop locally in downtown Provincetown instead. Start at the Canteen Holiday Market, which celebrates its 9th year in 2023 and brings over 25 artisans to its outdoor Christmas marketplace. You’ll find stalls of unique gifts and stocking stuffers, from handmade jewelry and ornaments to custom wreaths and whimsical hand-carved wooden Santas. You’ll meet the artists who made your gifts, adding a personal connection to the shopping experience. The restaurant also transforms its outdoor space into a European winter lodge ambiance, with special drinks like spiked cider and hot toddies alongside delicious and hearty food like beer-braised sausage and German potato salad. The Canteen’s market and holiday food menu occur every weekend from Thanksgiving through December 31st. There are plenty of other holiday shopping options within blocks, including Provincetown’s world-class galleries – perfect for getting a gift for the art lover in your family – and Provincetown Fudge Factory, where their selection of 20+ fudges and chocolate peppermint bark makes for delectable holiday sweet treats.

Holly Folly Weekend: Provincetown Events and Live Holiday Music Delights in December

Holly Folly comes to town soon after, on the first weekend of December, one of the liveliest holiday parties you’ll find anywhere and a celebration of Provincetown’s diversity and LGBTQ+ spirit. Although the pandemic put a damper on the Folly for a couple of years, it’s back in full swing again, with tons of Provincetown events on the calendar. The Jingle Bell Run’s festive fun happens on December 2nd, 2023, when participants dress up in Santa hats and do a casual run from Fanizzi’s to the Lobster Pot Tree, followed by a celebratory brunch at Provincetown Brewing Company. If running isn’t your speed, you can still join the morning crowds (the run starts at 10 am) along Commercial St and grab a beer and burger at the brunch, which benefits the Provincetown Business Guild’s work on behalf of the LGBTQ+ community.

During Holly Folly weekend and the following week, there are lots of chances to catch live music in town, all of the shows with unique holiday themes. On the evening of December 3rd, 2023, Jon Richardson croons at Crown and Anchor with his Holiday Hits show, paying tribute to Bing Crosby’s timeless renditions of holiday tunes in a cabaret style. On December 8th and 9th, the Outer Cape Chorale performs its annual free holiday show (this year’s title is “Glorious!” and includes the world premiere of the “Reindeer Cantata”) at the Provincetown Town Hall, conveniently located right across the street from your Provincetown lodging.

Polar Plunge Provincetown 2023 Winter Events.


First Light – Fireworks Over the Marina, Cold-Plunging for a Good Cause, and Ringing in the New Year in Style

After weeks full of festivities and holiday-themed Provincetown events, it all culminates with First Light when we ring in the promise and excitement of the new year with more shows, a spirited bar scene, and fireworks overlooking the bay. The Well-Strung String Quartet takes the Town Hall stage on December 30th, 2023, performing their entertaining mix of holiday songs and creative covers of Taylor Swift and Rihanna pop hits. On New Year’s Eve, head out for quality eats at spots within walking distance, like the hip gastropub Squealing Pig, followed by drinks and live music in the classy space at Tin Pan Alley.

Stroll over to the MacMillan Pier at dusk for the NYE fireworks show, when the sky over Provincetown Bay lights up with brilliant displays of explosive light. Shake off the wild night early on New Year’s Day morning by embarking on the Polar Bear Plunge with hundreds of others who take a ceremonial dip in the chilly waters of Provincetown Harbor. There’s a DJ playing music to pump you up before your plunge and free Manzanita coffee to warm you up afterward. And it’s all to raise money for the Center for Coastal Studies – a local non-profit that works tirelessly to conserve Cape Cod’s extraordinary marine ecosystem. Cap off the weekend with a scenic stroll along nearby Race Point Beach, a time of year when the summer tourists are a distant memory, and where you can catch the first spectacular sunset of 2024 at the end of the Cape.

Stay at our Provincetown Hotel this holiday season, the time of year when Provincetown shines bright!