The Holiday Season on the Outer Cape

^{Tammie Brown}

by Steve Desroches

The world seems a rather bleak place these days. So, it’s perhaps a good time to ask ourselves, “What would Auntie Mame do?” When the fabulous, free-spirited title character from the 1966 Broadway musical Mame loses her fortune in the stock market crash of 1929 and hard times are upon her, she decided that what’s needed to lift everyone’s spirit is the sparkle of the holidays. As the song “We Need a Little Christmas” says,  “Haul out the holly, Put up the tree before my spirit falls again, Fill up the stocking, We may be rushing things, but deck the halls again now.” The end of the year, being the darkest time in the Northern Hemisphere, is full of traditions, holidays, and customs that are not only about light, but community, generosity, and kindness. Those are all values that seek to unite us. As the fun of Halloween and the Spooky Season has passed the Outer Cape shifts towards the Sparkle Season. The coziness dial turns way up and the good times keep rolling. As is customary, with this being the last issue of Provincetown Magazine for the 2026 publishing season, we offer a run-down of some of the many things happening on the Outer Cape this holiday season. 

When we return in April it will be in part a celebration of 50 years of Provincetown Magazine! What began in 1977 continues to thrive, evolve, and reflect the arts and culture of the Cape tip. So, happy holidays and best wishes in the New Year. See you all again in spring of 2027! 

 

November / Thanksgiving

It’s appropriate enough that November kicks off with the sixth annual Provincetown Food and Wine Festival as we enter a season of frequent feasts. Tastings of all kinds take place at various restaurants and bars and a grand event at Town Hall that Saturday with accompanying parties and events. Special events include a pie eating contest at The Commons and the Miss Decanter Pageant at the Post Office Cabaret to find who has the Wit, Intelligence, Nuance, and Oenophilia to earn the title (for those following that spells out WINO). The contest will be hosted by Vivienne Fontaine and Raquel Blake, who also host Tringo, a mix of bingo and trivia, as well as Winter Break, a seasonal take on their Summer Camp events. Both are at the Post Office Café until they make a move over to Tin Pan Alley through to the spring. And speaking of drag and dining, the Post Office Café continues its drag brunches every Saturday through to the New Year.

Music abounds in November as the Coffeehouse at the Mews hosted by Peter Donnelly begins and continues every Thursday night through March. Donnelly also has two collaborations with local musicians as he and Jon Richardson perform their tribute to Simon and Garfunkel at the Provincetown Theater November 8 and Donnelly performs with singer-songwriter Grant King at the Provincetown Public Library on November 14. The Payomet Performing Arts Center goes on the road with Latin Grammy-nominated group Making Movies, with performances at the former Wellfleet Harbor Actors Theater (WHAT), now known as Outermost Performing Arts Center, on November 13 and in Provincetown at Fishermen Hall on November 14. The Center also hosts flutist Jessi Rosinski on the 14th with her show Between the Notes, a program that features music crossing cultures, centuries, and points of view. 

Wellfleet Preservation Hall on November 7 hosts Duo Andalus, performing in styles from Sephardic to Flamenco, Arabic to Ladino, their music bridges cultures across the Mediterranean Sea and North Africa in a performance that is as tender as it is powerful. The following night at Prez Hall features Walter Parks & The Unlawful Assembly, which reimagines and tributes historic spirituals and hymns which universally inspire, empower and unite.

The End End Music series presents Shadows on November 20, with performances by Brian Calhoon, Chan Collins, Claire Annette, Loren Lee, Marissa Miller, and Brian Raiche. And Tin Pan Alley is a musical hotspot all winter long. November also features some exciting theatrical offerings as the Provincetown Theater presents their production of The Search for Signs of Intelligent Life in the Universe, running November 19 through December 6. Just in time for Thanksgiving, William Mullin present his storytelling night The Tell at the Provincetown Theater on November 22 with the theme “Family Recipe” returning on December 12 with “Miracles” and again on January 16 with “Heroes.” And over at Outermost Performing Arts Center in Wellfleet, there is an exciting new theatrical pursuit with Paige O’Conner and Cody Sullivan called Readings, Readings, Readings Fest on November 22, a day-long theater-making and sharing event.

The holiday season goes into high gear with the annual lighting of the Pilgrim Monument, on November 25, the night before Thanksgiving in a tradition that marks a bit of a homecoming, too, for those from the Cape oiginally, who’ve returned for the holiday. The strings of light remain illuminated as a beacon through to the Epiphany on January 6. Another cherished tradition is the lighting of the Lobster Pot Christmas Tree in Lopes Square, scheduled for November 28. The day after Thanksgiving the Provincetown Business Guild presents Pink Friday, a day that promotes shopping at locally owned businesses as well as those that are LGBTQ owned and allied. And on November 27 the beloved Canteen Holiday Market opens on weekends through to the New Year offering locally made goods, with special holiday tea dances scheduled throughout the season.

Holly Folly / Christmastime

Founded by the Provincetown Business Guild (PBG) in 1997 Holly Folly is celebrating its 29th year. But as has become custom the LGBTQ holiday celebration, which kicks off on the first weekend in December, now takes every weekend up until the New Year, when Provincetown offers its First Light festivities. Holly Folly offerings includes Tammie Brown’s Holiday Sparkle show at Red Room on December 5, while over at the Post Office Cabaret Mike Flanagan and Sheree Marcelle present A Soulful Christmas that Saturday while Paige Turner presents Make The Yuletide Gay on December 4 and 11. Meanwhile A Woman Named Carlos performs Carlos on Carols every Saturday night November 21 through December 19 and Drag Brunches are scheduled for every Saturday in November and December. Over at the Pilgrim House Jon Richardson brings back his popular show Bing: The Holiday Hits as he sings Christmas songs made famous by Bing Crosby, featuring special guests Peter Donnelly, Dan McGhie, Brittany Rolfs, and Peter Toto. Other Holly Folly events includes the annual Jingle Bell Run, the Inn Stroll,  a Holiday Bar Crawl, Holiday Bingo, a sing-along trolley ride, and a special screening of the 1958 film Auntie Mame. 

Provincetown Town Hall  is hopping the first weekend in December when on Friday night the PBG presents the Holly Dolly Follies. Hosted by Thirsty Burlington and Mackenzie this holiday variety show features more than a dozen Provincetown performers and will include a tribute to the late Dolly Parton. A portion of the proceeds will be donated to Dolly Parton’s Imagination Library. Come Saturday night at Town Hall the Boston Gay Men’s Chorus presents Holigays, performing pop anthems, diva moments, and holiday classics. Come December 11 and 12 the Outer Cape Chorale and Chamber Singers take over Town Hall and present Castles & Revelry: Baroque to Broadway, featuring excerpts from Handel’s Alexander’s Feast; selections from Les Miserables, Quest for Camelot, Man of La Mancha, Cinderella, a fun Gilbert and Sullivan ditty, and “Be Our Guest” from Beauty and the Beast. There’s more music over at the Provincetown Theater with their annual Townie Holiday Extravaganza taking place December 17 through December 20. The Great Music series at the Unitarian Universalist Meeting House presents Joy to All: Music for Happy Holidays on December 5 featuring a dozen musicians performing inspirational music and holiday classics. And throughout the month keep an eye out for holiday parties at the Atlantic House, the Crown & Anchor, Gifford House, Shipwreck Lounge, Pilgrim House, and Harbor Lounge. 

New Year / First Light

Provincetown is a fabulous place to ring in the New Year. It’s both cozy and quaint as well as lively and fun. Once again on New Year’s Eve a drone show will take place over Provincetown Harbor at 6 p.m. to get the evening’s festivities off to a gorgeous start. First Light, the Provincetown Business Guild’s New Year celebration, also features drag bingo and the Polar Plunge on New Year’s Day when the brave (or crazy) dive into the chilly waters of Provincetown Harbor as a fundraiser for the PBG, which not only produces First Light, but also Holly Folly, Provincetown Pride, and Carnival as well as promotes the town to the LGBTQ community. To celebrate the new year the Provincetown Bicycle Committee organizes the Light Bright Bike Ride on December 31. Those interested should meet at the Provincetown Public Library ready to roll out onto Commercial Street at 4:30 p.m. Come early to decorate your bicycle with lights or arrive ready to go. And make sure to check out the A House, Crown & Anchor, Gifford House and more as the bars and nightclubs of Provincetown are allowed to stay open until 2 a.m. on New Year’s Eve.

The holiday season comes to a close in Provincetown with Re-Rooter’s Day, a holiday started by artist Jay Critchley in 1983. On January 7 at sunset, revelers gather on the flats of the East End in a ceremony to “re-root” themselves back to the Earth after the excesses of the holiday season. Critchley leads the crowd in whimsical chants and songs before he drags a small cardboard boat with an old Christmas tree out into the water to light it aflame. 

Off Season / Winter

Ask anyone who lives in Provincetown and the most common question anyone gets asked is “What’s it like in the winter?” First of all, it’s absolutely beautiful and the season actually attracts visitors who prefer the town as its most quiet. Secondly, while it is certainly not as crowded as any other time a year, it’s one of the most creative and the artistic community dives into its works. 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. The Film Art Series curated by Howard Karren, a partnership between PAAM and the Provincetown Film Society now in its 20th year, brings art-house cinema and conversations to Provincetown November through May with screenings at the Waters Edge Cinema. Provincetown’s community radio station WOMR hosts movie nights every Thursday through March screening classic films shown on actual reel to reel film with silent movies shown with live musical accompaniment. Opera fans assemble monthly in Wellfleet as Outermost Performing Arts Center hosts live HD broadcasts from the Metropolitan Opera in New York through May. The A-House continues the ever-popular bingo every Wednesday hosted by Tiki Bronstein (Thirsty Burlington) as well as Liza Lott. Valentine’s Day falls on a Sunday in 2027, which means that weekend will be more crowded than usual as people come to town for a romantic getaway. The leather community fills the town for Snowbound Leather Weekend February 19 to 21 and the bears take over for Out of Hibernation set for March 11 through 14. 

Atlantic House, 4 Masonic Pl., 508.487.3169, ahouse.com.
Canteen Holiday Market, 225 Commercial St., 508.487.3800. thecanteenptown.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.
Outermost Performing Arts Center (formerly Wellfleet Harbor Actors Theater), Rte. 6, 508.349.9428, outermostpac.org.
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-monument.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.
St. Mary’s of the Harbor, 517 Commercial St., 508.487.2622. stmaryoftheharbor.org. 
Shipwreck Lounge, 10 Carver St., 508.487.9005. brasskey.com.
Tin Pan Alley, 269 Commercial St., 508.487.1648. tinpanalleyptown.com.
Unitarian Universalist Meeting House, 236 Commercial St., 508.487.9344. ptownmusic.com.
Waters Edge Cinema, 237 Commercial St., 508.487.3456. provincetownfilm.org.
Wellfleet Preservation Hall, 335 Main St., 508.349.1800. wellfleetpreservationhall.org.
WOMR, 494 Commercial St., 508.487.2619. womr.org.