^{Courtesy of Provincetown Business Guild}

The Holiday Season on the Outer Cape

by Steve Desroches

In “Auld Lang Syne” there’s a line about toasting to the past with a “cup of kindness,” making it clear as to how it became a traditional song to celebrate the New Year. In the darkest time of the year, and in a country where cruelty, callousness, and ignorance are held as ideals by many in power, it can be difficult to revel in the holidays of the season. But that is exactly why these holidays are so important. It’s not about stuffing our faces, buying crap no one needs or even wants, or drinking oneself into oblivion. They are about gratitude and generosity, creating light in the dark, empathy and charity, and yes, joy, fun, and celebrating community. 

Here in Provincetown, visitors often express that the Cape tip is their escape, happy place, or that it’s magical. But the town is not immune to the real world, of course. The element that creates that feeling of belonging, peace, and bliss is not innate. It comes from a choice and commitment that requires all of us to ensure what makes Provincetown special continues to thrive. In fact, doing so is an effective act of resistance against the dark forces that seem unstoppable. History shows us that they are not. By doubling down on what makes the Outer Cape a refuge for some many often pushed to the fringes of society, be it in work or play, is important. Even taking a rest from the news and the state of affairs is effective. The holiday season on the Outer Cape continues to grow in events, gatherings, and celebrations, especially in Provincetown. Mixing the cozy and the camp, Provincetown is all about community this time of year, and it’s a beautiful thing. Here’s a partial outline of many of the happenings on the Cape tip in November, December, and on into the New Year. Here’s to kindness in 2026! And who knows…maybe three ghosts will visit the White House on Christmas Eve.

Once the wonderful frenzy of Halloween in Provincetown has passed, the town settles into a new, cozy and chill vibe.The beloved Coffeehouse at the Mews open mic night has returned to the Mews Restaurant on Mondays through mid-May, hosted by Peter Donnelly and Ron Robin. On November 6, Payomet is bringing Natalie Merchant to Provincetown Town Hall for a concert to remember. Payomet is also taking over the stage at Wellfleet Harbor Actors Theater (WHAT) with the folk, rock, blues-inspired Chastity Brown on Saturday, November 8 and Big Yellow Taxi, a Joni Mitchell tribute band, on Sunday, November 9. 

With thoughts shifting toward Thanksgiving, it’s perfect that the Provincetown Food & Wine Festival takes over town November 6 through 9 with a full schedule of tastings, offering an opportunity to sample the creations of local restaurants and chefs.  That same weekend, actor and playwright Cody Sullivan presents his latest work The Dune Inn, a play at The Wilde at the Gifford House about the housing crisis in Provincetown that is sure to feature Sullivan’s quick wit and wonderful satirical observations.

Over at Pilgrim House, Tori McClain and Dru Daniels present Vexed: A Sapphic Story from Oz every weekend through January, as will Liza Lott who will host Karaoke Queen every Friday and Saturday. Throughout November and December the musical hotspot Tin Pan Alley is hosting live music nightly, featuring Mike Flanagan Sundays and Wednesdays, Jim Brosseau Mondays, Billy Hough and Darlene Van Alstyne Tuesdays, Jake Glass and Joshua Giant Thursdays, Brittany Rolfs and Patrick Dorrow Fridays, and Peter Toto Saturdays. And the Crown & Anchor hosts the annual Mr., Ms. or Mx. New England Leather contest with several days of events, November 21 – 23.

Thanksgiving

The holiday season kicks off in a bright and beautiful way with the annual lighting of the Pilgrim Monument, this year on the night before Thanksgiving, Wednesday, November 26. Festivities begin at 3 p.m. with music by DJ Emerson and the lights will be switched on at 5:15 p.m. The gathering on High Pole Hill is always festive and fun, but over the years anywhere with a view of the monument has become host to lighting parties, be they private homes or bars and restaurants, and afterwards the town livens up for an evening to celebrate the Provincetown beacon which stays lit until the Epiphany, or Little Christmas, on January 6. 

Getting a jump start on the holidays, the Provincetown Theater presents a hilarious and heartfelt adaptation of A Christmas Carol by Doris Baizley from November 20 to December 7. This fresh look at the Charles Dickens classic features a traveling vaudeville troupe during the Great Depression who realize that their Scrooge and Tiny Tim might’ve been left behind in the last town they played. Regardless, the show must go on, and as the actors scramble with unusual recasting and last-minute changes, the play delivers big laughs and surprises. Earlier in November, the theater presents The William TELL, a new story-telling night hosted by William Mullin, with the theme “Home for the Holidays” on the 15th and “Locals and Washashores” on December 13, with plans for dates throughout the winter. 

RuPaul’s Drag Race star Tina Burner opens her new holiday show, Low Elf-Esteem, at the Crown & Anchor Thanksgiving weekend as she looks to put the self-help back into being Santa’s Little Helper. The show runs to December 6. And if you recovered from a big Thanksgiving meal head over to Anita Cocktail’s Drag Brunch, which runs every weekend through January 4, while the Drag Brunch at the Post Office Café is running now through December 28. And shaking things up over at Pilgrim House is British drag superstar Lady Camden returning to Provincetown after making her smash hit debut this past summer with shows November 20 – 28. 

The beloved Canteen Holiday Market opens Thanksgiving weekend, returning each weekend until the New Year. And of course local restaurants offer special Thanksgiving menus and clubs and bars like the Crown & Anchor, Atlantic House, the Gifford House, Shipwreck Lounge, Tin Pan Alley, and more offer places to dance the night away or sit for a cozy drink with friends. 

Holly Folly

Nearing its 30th anniversary, Holly Folly has become a significant celebration on the Provincetown calendar of events. Presented by the Provincetown Business Guild, this year Holly Folly is expanding with the kickoff December 5 – 7 and additional celebratory weekends December 12 – 14 and 19 – 21. Events for the kickoff weekend include the Holly Folly Follies: A Gay Holiday Extravaganza, a variety show presented by the Crown & Anchor at Provincetown Town Hall on Friday, December 5, and the following night the Boston Gay Men’s Chorus takes over Town Hall with their concert, Holigays!  During the day on Saturday strip down to your Speedo or bikini and join in the Holly Folly Jingle Bell Run down Commercial Street starting at the Mews Restaurant and ending at the Bay Café for a chance to warm up at the Holly Folly Brunch and close out the weekend with Holly Folly Bingo Sunday afternoon at the Crown & Anchor. And don’t miss the fabulous Thirsty Burlington in Christmas is Cher-ing, December 6. 

Throughout weekends in December take in the Holly Folly Gallery Stroll, the Snowball Bar Crawls, and the Holly Folly Inn Strolls for a chance to explore the galleries, bars and lounges, and guest accommodations in Provincetown. And don’t forget that the Crown & Anchor, Atlantic House, the Gifford House, and the Shipwreck Lounge are hopping on weekends.

Also starting the first Holly Folly weekend is Anita Cocktail at the Crown & Anchor with a brand new holiday show that runs every Saturday in December. Returning to Pilgrim House is Plasma with her show Have Yourself A Plazzy Wazzy Christmas, running December 4 through 21. Red Room keeps the holiday cheer in motion with Jackie and Jan’s Jingle Jam: The Remix Tour featuring RuPaul’s Drag Race stars Jackie Cox and Jan Sport on Friday, December 5 and Saturday, December 6, and A Young and Original Christmas, a TikTok musical sensation, with a holiday concert with special guest Yaron Spiwak Saturday, December 6 and Sunday, December 7. And every Saturday in December Red Room hosts Santa Con Tea Dance where everyone is invited to come in festive attire for this ho, ho, ho of a tea dance. The Post Office Café and Cabaret present the musical styling of Mike Flanagan with Lauren Scales on Saturday, December 6 for A Soulful Christmas, with Flanagan performing every Friday in December with Keb Hutchings, followed by Vivienne Fontaine and Raquel Blake presenting Homo for the Holidays, and every weekend is the café’s popular Drag Brunch. Also tapping into the season of music and merriment is the Outer Cape Chorale with their concert performance Points North!, featuring the work of Canadian composers on Friday, December 12 and Saturday, December 14 at Provincetown Town Hall. And in Wellfleet at WHAT, the Lower Cape Outreach Council raises money for their Fuel Assistance Program with Yule for Fuel, a benefit variety show hosted by Stephen Russell on December 13 and 20.

Christmas/New Year/First Light

The week between Christmas and New Year’s Day feels a bit like an old school vacation week as the town jingles and jangles with shows, hopping nightclubs and bars, and good times galore. As the Provincetown Business Guild produces First Light, and businesses across town present their own contributions. Pilgrim House gets things going with RuPaul’s Drag Race star Eureka O’Hara and her holiday show The Divorce Claus: Mrs. Claus As You’ve Never Seen Her with eight performances between December 23 and January 3. Getting in on the fun is Latrice Royale with Why It Gotta Be White Christmas?! Friday, December 26 through Sunday, December 28, also at Pilgrim House, where she will also host the New Year’s Eve Fantasy Ball with a guest performance by Lakia Mondale on December 31. And remember on New Year’s Eve last call is at 2 a.m., giving revelers an extra hour to party into 2026 at the bars and nightclubs around town. 

Kicking off the festivities on New Year’s Eve is the annual fireworks display over Provincetown Harbor at dusk, and if you’re the adventurous sort, you can participate in the Provincetown Polar Bear Plunge on New Year’s Day where hundreds take a dip into the cold waters of the harbor. The holiday season in Provincetown of course has its own unique end. Every January 7, artist Jay Critchley presents Re-Rooters Day. Started in 1983, people gather on the beach in the East End at sunset to re-root themselves back to the Earth by symbolically discarding things from the previous year as Critchley leads the crowd in Dr. Seuss like recitations and finally by lighting an old Christmas tree aflame as it floats off into Provincetown Harbor.

Off Season/Winter

Some call it the off season, but that term seems to be fading in use as it’s a misnomer that Provincetown is dead in the winter. In addition to Provincetown being beautiful in the winter, it’s often also when the town can be intensely creative as writers, artists, and performers use the time to focus and present their work without the distraction of tourists and day jobs. The Fine Arts Work Center (FAWC) hosts monthly FAWC Fridays, featuring live music and food trucks as the public is invited to see and hear the work produced by the fellows in residence. The Provincetown Art Association and Museum (PAAM) features exhibitions year-round, as well as speakers and special events. 

If you’re a film lover, you are in luck, as Provincetown is home to several special film series all winter, including the Film Art Series, a partnership between PAAM and the Provincetown Film Society now in its 19th year that brings art-house cinema and conversations to the Waters Edge Cinema, November through May. Provincetown’s community radio station WOMR also hosts movie nights every Thursday through March, screening classic films shown on actual reel-to-reel film, and silent movies are shown with live musical accompaniment. Also on Thursday nights all winter and spring the Crown & Anchor hosts Two Queens and a Movie, hosted by Liza Lott and Anita Cocktail, showing camp and cult classics. 

Opera fans assemble monthly in Wellfleet as WHAT hosts live HD broadcasts from the Metropolitan Opera in New York through May, and lovers of RuPaul’s Drag Race can get their fix with weekly viewing parties at the Crown & Anchor starting in January. Over at the A-House, Thirsty Burlington hosts bingo every Wednesday in what has become a beloved community tradition. 

Leather enthusiasts fill the town for Snowbound Leather Weekend February 20 to 22 and the bears take over for Out of Hibernation set for March 6 through 8. The wildly talented and creative Cody Sullivan continues his Cody Plays, in which an original play is created in just a day, at the Gifford House the last Monday of every month through May. And Wellfleet Preservation Hall hosts live music, film screenings, readings, and theatrical events all year long, being an important community gathering spot throughout the winter.

Venues

Atlantic House, 4 Masonic Pl., 508.487.3169, ahouse.com.
Canteen Holiday Market, 225 Commercial St., 508.487.3800. canteenholidaymarket.com.
Crown & Anchor, 247 Commercial St., 508.487.1430, onlyatthecrown.com.
Fine Arts Work Center, 24 Pearl St., 508.487.9960. fawc.org.
Gifford House, 9 Carver St., 508.487.0688. gifford.house.
The Mews Restaurant, 429 Commercial St., 508.487.1500. mewsptown.com.
Provincetown Art Association and Museum, 460 Commercial St., 508.487.1750. paam.org.
Pilgrim House, 336 Commercial St., 508.487.6424. pilgrimhouseptown.com.
Pilgrim Monument and Provincetown Museum, 1 High Pole Hill Rd., 508.487.1310. pilgrim-monuement.org.
The Post Office Café and Cabaret, 303 Commercial St., 508.487.0006. postofficecafe.net.
Provincetown Business Guild, 115 Bradford St., 508.975.6394. ptown.org.
Provincetown Theater, 238 Bradford St., 508.487.9793., provincetowntheater.org.
Red Room, 258 Commercial St., redroom.club.
Shipwreck Lounge, 10 Carver St., 508.487.9005. brasskey.com.
Tin Pan Alley, 269 Commercial St., 508.487.1648. tinpanalleyptown.com.
Waters Edge Cinema, 237 Commercial St., 508.487.3456. provincetownfilm.org.
Wellfleet Harbor Actors Theater, Rte. 6, 508.349.9428, what.org.
Wellfleet Preservation Hall, 335 Main St., 508.349.1800. wellfleetpreservationhall.org.
WOMR, 494 Commercial St., 508.487.2619. womr.org.