Arts, Hearts, Leather, and Bears in Provincetown

The Provincetown Business Guild (PBG) welcomes visitors to Provincetown for the first events of 2023 this February and March, including Valentine’s Day, a Winter leather and fetish gear gathering, and an inclusive, welcoming weekend for the bear community. 

The Provincetown Schools, the PBG, and the Commons are partnering to raise funds for Middle Year students to travel to London in May of 2023. Art with a Heart is a Valentine’s Day Art Fair at the Commons on Saturday, February 11, and Sunday, February 12, 10:00 am – 2:00 pm. Pieces for sale start at just $50. 

Artist and Commons board member Mark Adams has donated his time to hold a Drawing Workshop on January 28 for students, parents, and community members. During the workshop, participants will create pieces of art that will be donated to the Art Fair and help raise funds for the students’ trip to London. Additional work will be donated and available for sale at the Fair. Provincetown Schools students (between the ages of 11-13) will serve as docents at the art fair to showcase their art and the works of local artists and community members.  

March in Provincetown

“We jumped at the chance to work with the Commons and the Provincetown Schools to support the students and encourage the next generation of Provincetown artists,” said Stephan Hengst, executive director of the Provincetown Business Guild.

The popular Provincetown Follies variety show returns Friday, February 10, with a Saint Valentine edition at the Crown & Anchor’s Paramount Club. Local performers will ignite the senses with singing, dancing, drag, burlesque, comedy, and more. Proceeds from this show’s ticket sales benefit the Provincetown Performing Arts Fund.

On Saturday, February 11, the Crown & Anchor presents Dall’Italia Con Amore (From Italy with Love), a 5-course prix fixe dinner with wine pairings. Dishes will be prepared using Crown & Anchor’s co-owner, Paolo Martini’s treasured Italian family recipes, with Jonathan Hawkins adding to this valentine’s feast with live entertainment from Provincetown performers Jon Richardson, Mackenzie, Hilarie Tamar, João Santos, Spookey, Austin Tyler, and more. 

Later in February, “Get Outta The Cold And Into The HEAT!” at the fifteenth Snowbound Leather Weekend filled with brunches, parties including White Out, Chaps & Straps, Hops & Bottoms, and a good old fashioned Beer Blast. Ahead of the weekend, attendees are encouraged to submit photos in their best winter-themed leather/fetish gear to be displayed at the Snowbound events for attendees to vote for their favorite. Suggested donations of $10 will serve as a vote for the best photo. The man with the most votes (money raised) will be Mr. Snowbound 2023. All funds raised will be donated to ASGCC (AIDS Support Group of Cape Cod). 2022’s Snowbound Leather weekend raised almost $18,000, the most ever raised in the event’s 14-year history.

“Last year was the first time I had attended Snowbound Leather Weekend in Ptown, and I felt so welcomed and accepted,” said Cameron Peirce, Mr. Snowbound 2022. “I was thrilled to fundraise and give back to the community that had accepted me with open arms. It has been an honor to wear the sash and represent the Provincetown and leather/fetish communities across the country, communities I care deeply about.” 

Another anticipated winter weekend in Provincetown is Out of Hibernation. Organized by the Northeast Ursamen and the Crown & Anchor, the event is a celebration of the coming spring for the Bear community and their friends featuring parties, contests, games, and more, including Tough Drag Bingo and the Bears and Boxers Party.

“Out of Hibernation is a great opportunity to experience a Bear-centric getaway in Provincetown that is less crowded, more affordable, and more intimate,” said Hengst. “We love July’s Bear Week celebration, but also know that it is not for everyone and encourage Bears, Cubs, Otters, Wolves, and their friends to enjoy Provincetown during Out of Hibernation.”

Many Provincetown businesses welcome visitors year-round. For the complete list of lodging, dining, bars, galleries, retail, attractions, and services open in Provincetown during the winter, visit


Art with a Heart Valentine’s Art Fair

February 11 & February 12

10:00 am – 2:00 pm

The Commons

46 Bradford Street

Provincetown’s Follies Saint Valentine’s Edition

8:00 pm

The Paramount Club at the Crown & Anchor

247 Commercial Street

$25 general admission/$35 VIP preferred seating 


My Slutty Valentine Underwear Party

9:00 pm

The Vault at the Crown & Anchor

247 Commercial Street

$5 cover donated to ASGCC (AIDS Support Group of Cape Cod)

Dall’Italia Con Amore (From Italy with Love)

7:00 pm

5-course Prix Fixe Italian Dinner with wine pairings and entertainment

The Restaurant at the Crown & Anchor

247 Commercial Street



My ______ Valentine, Comedy at the Crown

7:30 pm

The Wave Bar at the Crown & Anchor

247 Commercial Street



Tunnel of Love, a Valentine’s Day Queer Formal

9:00 pm

The Paramount Club at the Crown & Anchor

247 Commercial Street

$5 advance/$10 door


Snowbound Leather Weekend XV

February 24-26

Various venues

Tickets and schedule:

Out of Hibernation

March 10-12

Various venues

Tickets and schedule:

About the Provincetown Business Guild

The Provincetown Business Guild is a nonprofit organization promoting and supporting the lesbian, gay, bisexual, transgender, and queer business community in Provincetown, MA. The Guild is committed to improving the Provincetown community by advocating for the acceptance of diversity and tolerance through projects, programs, and education. The Guild welcomes residents and visitors to experience America’s first LGBTQ+ tourist destination. For more information about the Provincetown Business Guild, visit and on Instagram @VisitPtown.

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