Name: Holiday Cheers: Seasonal Sip & Soups at Truro Vineyards
Start: 2025-12-05
End: 2025-12-05
Location: Truro Vineyards

The nation’s largest and oldest LGBTQ+ Holiday Celebration, Holly Folly, first began in 1997 as an opportunity to gather and celebrate the Holiday season with our chosen family in Provincetown. Today the queer community travels from far and wide to enjoy great performance art, fine dining and holiday shopping experiences from the truly unique shops, boutiques and galleries that line Commercial Street.

Celebrate the Holidays in Provincetown Holly Folly Kickoff Weekend: December 5-7, 2025 Plus Expanded Holly Folly Weekends: December 12-14 & 19-21, 2025

Scroll down to see pics from previous Holly Folly celebrations and plan to join us in Provincetown this holiday season for our 2025 celebration kicking off December 5th-7th and expanding for the first time ever, through the entire month of December!

Plan Your Holly Folly Trip to Ptown

First Light: New Year's Weekend

Ring in the New Year on the tip of Cape Cod with fireworks, the annual Polar Plunge & more.

December 26, 2025 - January 1, 2026

Thank You to Our Community Partners + Sponsors

Featured Holly Folly 2025 Events

It's Ornamental Henny! A Holly Folly Decorating Contest

This year, Let it Glow and show off your Holigay Spirit by joining the "It's Ornamental Henny!" Holly Folly Decorating Contest! Here's your chance to showcase the Best Retail Window Display, Best Interior Business, Best Exterior Business (and) Best Exterior Home in town! We know you have the skills to Sleigh it Ptown!

More Information to Come!

Holly Folly Follies: A GAY Holiday Extravaganza!

Bring in the holidays with a super special holiday version of the Provincetown Follies presented by The Crown & Anchor in historic Town Hall. Many of Provincetown’s iconic performers usher in the holiday season in true Provincetown style - do not miss this show! Tickets available SOON at onlyatthecrown.com

Friday, December 5th at 8:30pm

Holly Folly Gallery Stroll Saturdays

Find the perfect Provincetown gift on this special holiday-edition gallery stroll by roving Commercial St. through our many unique gallery spaces. This event is hosted by the Provincetown Art Gallery Association.

Saturdays, Dec 6th, 13th, 20th & 27th from 1-4pm

Annual PBG Holly Folly Jingle Bell Fun Run & Brunch Fundraiser (NEW LOCATIONS)

One-horse-open-slay your way down Commercial Street in as little clothing as you dare for this frosty fun-run! Folks will gather this year at the newly remodeled The Mews restaurant for coffee, strip down, and run through Provincetown to the Lobster Pot Tree at Lopes Square before climbing into their favorite onesie for a celebratory Holly Folly Brunch and Live Music at Bay Cafe!

Saturday, December 6th from 9am-12pm

Provincetown's Famous Holly Folly Inn Strolls

Pop your antlers into some of Provincetown's most iconic inns for warm decor, treats & more! Make sure to map out your stroll and swing by one of the many artisan markets available on the same day to find your favorite stocking stuffers.

Saturdays, Dec. 6th & 20th from 1-5pm

The Boston Gay Men's Chorus: Holigays!

Get ready to ring in the holiday season with the Boston Gay Men’s Chorus like never before! We’re thrilled to invite you to HOLIGAYS! an electrifying holiday show to dazzle and delight! Tickets on sale in mid-September!

Saturday, December 6th at 8pm

Holly Folly BINGO

Come together on the Sunday of Holly Folly and frolic in the Bingo Balls to help make the holigays even more merry & bright!

Sunday, December 7th at 1pm

The Snowball Bar Crawls

Wine & wassail your way through the streets of Provincetown hitting your favorite watering holes with tons of friendly, holiday revelers, drag queens (and maybe even glimpse a sighting of St. Nicholas while snowballing your way through Provincetown!)

Saturday, December 13th & 27th from 1-5pm

All Holly Folly 2025 Events

Holiday Cheers: Seasonal Sip & Soups at Truro Vineyards

Raise a glass as we unveil a new Pinotage and wine label by Pete Hocking, and enjoy seasonal spirits from Truro Vineyards paired with warm soups from Blackfish Bistro – all within the newly winterized pavilion.

Friday December 5th

5:30 pm – 7:30 pm

Truro Vineyards

11 Shore Road (Route 6A) North Truro, MA 02652

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BING: The Holiday Hits with Jon Richardson

Bing Crosby’s voice will forever define the music of the Holiday season! Joined by a talented cast of musicians, Jon Richardson will take you for a walk down memory lane and will bring you nostalgia, hope, and Christmas cheer.

Friday December 5th

6:00 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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Tina Burner’s LOW ELF ESTEEM

This holiday season, RuPaul’s Drag Race All-Star and National Miss Comedy Queen Tina Burner has Low Elf-Esteem. While everyone else is helping themselves to candy canes and festive fun, this melancholy elf is just hoping to put the (self) help back in Santa’s Little Helper.

Friday December 5th

7:00 pm

Paramount Room @ Crown & Anchor

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Tammie Brown’s Holiday Sparkle

Tammie Brown’s annual Christmas Show- The Holiday Sparkle. Featuring Tammie’s Holiday hits and special guest appearances.

Friday December 5th

7:00 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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Holly Folly Follies

Get ready to spread queer cheer as The Crown & Anchor and Prouder Together kick off their Spread Queer Cheer Tour with the Holly Folly Follies — a super special holiday edition of the Provincetown Follies, live at historic Provincetown Town Hall.

Friday December 5th

8:00 pm

Provincetown Town Hall

260 Commercial Street, Provincetown

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2025 Annual Jingle Bell Fun Run & Holly Folly Brunch

One-horse-open-slay your way down Commercial Street in as little clothing as you dare for this frosty fun-run! Folks will gather at The Mews (429 Commercial Street) for coffee, strip down, and run through Provincetown to Lopes Square / The Lobster Pot Tree before climbing into their warmest onesie for the Jingle Bell Brunch at Bay […]

Saturday December 6th

9:00 am – 12:00 pm

The Mews

429 Commercial Street

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Souper Saturday

Join us for a warm cup of soup from over 25 of our local restaurants and businesses at our annual Holly Folly fundraiser, SOUPER SATURDAY.

Saturday December 6th

11:00 am – 2:00 pm

Tin Pan Alley

269 Commercial Street, Provincetown, MA 02657

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SANDY CLAUS: Santa’s older, gayer, drunker sister

Kristen Becker’s Sandy Claus (Santa’s Gay Older Sister) returns in a new interview-style show with Marissa Miller!

Saturday December 6th

2:00 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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Clove & Creek Wreath Making Workshop

Join Jeffrey Pratt from Farm and Son for a wreath making workshop at our Provincetown location on December 6, 3-5p. All wreath making materials and refreshments will be provided.

Saturday December 6th

3:00 pm – 5:00 pm

Clove & Creek

353 Commercial, Provincetown MA

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Santa Con Tea Dance

Ho,Ho,Ho it’s the Holly Folly Tea Dance, back with one every weekend in December. Throw on your best Santa style and come have a twirl in the decked halls of Red Room. A annual tradition. Rotating DJS playing classic dance hits with a touch of Holidays.

Saturday December 6th

4:00 pm – 7:00 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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BING: The Holiday Hits with Jon Richardson

Saturday December 6th

5:30 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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Mike Flanagan’s ‘A Soulful Christmas’ with Lauren Scales

From Mike’s arrangements of Christmas classics, singalongs, movie visuals, gifts, and more, this show will put you in the holiday spirit!

Saturday December 6th

6:00 pm

Post Office Cafe & Cabaret

303 Commercial Street, Provincetown, MA 02657

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Tina Burner’s LOW ELF ESTEEM

Saturday December 6th

7:00 pm

Paramount Room @ Crown & Anchor

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Tammie Brown’s Holiday Sparkle

Tammie Brown’s annual Christmas Show- The Holiday Sparkle. Featuring Tammie’s Holiday hits and special guest appearances.

Saturday December 6th

7:00 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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Anita Cocktail’s DRAG SHOW: HOLIDAY EDITION

Get into the holiday spirit with Anita Cocktail and friends in a BRAND NEW Holiday Themed Show! A mix of live singing, lip sync and comedy, Anita Cocktail’s DRAG SHOW: Holiday Edition will deliver killer vocals, incredible performances and holiday cheer sure to make your yuletide gay!

Saturday December 6th

7:30 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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Thirsty Burlington in Christmas is Cher-ing!

Holly Folly would not be the same without Thirsty Burlington. Please join Thirsty in her brand new Holiday spectacular “Christmas is Cher-ing!” With stunning costumes and featuring all your favorite classic holiday songs, as well as some new ones! This show is one not to be missed.

Saturday December 6th

8:30 pm

Paramount Room @ Crown & Anchor

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A Young and Original Christmas

This unforgettable show blends traditional and unconventional Christmas songs with the band’s own original holiday material, delivering a magical, heartwarming, and wildly entertaining night of music. Don’t miss these two special performances at The Red Room!

Saturday December 6th

8:30 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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Brunch with the Chorus Boys

Join the Boston Gay Men’s Chorus for a festive, gourmet brunch fundraising reception and help us sustain our mission to inspire change through music.

Sunday December 7th

11:00 am

Porch Bar @ Gifford House

9 Carver Street, Provincetown MA 02657

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A Very Merry Burner Brunch

HO HO HO – It’s A VERY MERRY BURNER BRUNCH. Rupaul’s Drag Race star and National Miss Comedy Queen Tina Burner welcomes all sinners to an offering of laughs, live singing and signature mixes.

Sunday December 7th

11:00 am – 3:00 pm

Provincetown Brewing Company

247 Commercial Street, Provincetown, MA 02657

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BING: The Holiday Hits with Jon Richardson

Sunday December 7th

2:00 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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A Young and Original Christmas

Sunday December 7th

3:00 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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The BIG GAY Holiday Movie Musical Extravaganza

Attend an exclusive screening of beloved Christmas films and TV specials, showcasing iconic scenes and interactive sing-alongs. Explore classic favorites, witty satire, Hanukkah celebrations, and romantic delights, complemented by live singing, popcorn and eggnog.

Sunday December 7th

5:00 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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The BIG GAY Holiday Movie Musical Extravaganza

Friday December 12th

7:00 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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The Outer Cape Chorale Presents “Points North!”

The Outer Cape Chorale’s free December 2025 concert titled “Points North” features stunning choral works by composers from above the 49th parallel. It will be performed Friday, Dec. 12 at 7PM and Saturday, Dec. 13 at 5PM at Provincetown’s beautifully restored Town Hall.

Friday December 12th

7:00 pm

Provincetown Town Hall

260 Commercial Street, Provincetown

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Santa Con Tea Dance

Saturday December 13th

4:00 pm – 7:00 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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The Outer Cape Chorale Presents “Points North!”

Saturday December 13th

5:00 pm

Provincetown Town Hall

260 Commercial Street, Provincetown

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BING: The Holiday Hits with Jon Richardson

Saturday December 13th

5:30 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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Anita Cocktail’s DRAG SHOW: HOLIDAY EDITION

Saturday December 13th

7:30 pm

Cabaret @ Crown & Anchor

247 Commercial Street, Provincetown, MA 02657

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A Very Provincetown Christmas

“A Very Merry Provincetown Christmas” is Provincetown’s brand-new holiday variety show — hosted by Bob Keary and musically directed by Yaron Spiwak! Think glittering lights, heartfelt duets, and just the right amount of camp — a festive throwback to the era when every star had their own holiday special.

Saturday December 13th

8:30 pm

Red Room

258 Commercial Street, Provincetown, MA 02657

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The Outer Cape Chorale Presents “Points North!”

The Outer Cape Chorale’s free December 2025 concert titled “Points North!” features stunning choral works by composers from above the 49th parallel. It will be performed on Sunday, Dec. 14 at 3PM at our NEW VENUE – the Nauset Regional High School!

Sunday December 14th

3:00 pm

Nauset Regional High School

100 Cable Rd, Eastham, MA 02642