The Devil Wears Payless

Matt Alber returns to Provincetown for Bear Week, making his Post Office Cabaret debut! Matt is a two-time Grammy® Award-winning recording artist, filmmaker and youth mentor based in Portland, OR. His original songs and reinterpretations of pop classics appear regularly on television series' like 911 (FOX), The Fosters (ABC Family) & 911 Lonestar (FOX.) Notable appearances include sold out performances at Lincoln Center in New York on the esteemed American Songbook Series and featured soloist at the opening ceremonies of the Gay Olympic Games in Chicago at Soldier Field. As a filmmaker, Matt focuses on the stories of LGBTQ+ youth & elders. His current docu-series, Queer As Fundamental (Queer AF*) features the life stories of six young Queer artists on a journey to express how they fundamental to the fabric of life. To learn more, visit: www.queeraf.tv

Matt Alber brings his sharp wit and musical talent to the Post Office Cabaret stage—a performer who knows how to work a room and make you feel seen. Expect clever storytelling woven through original songs and covers, the kind of show that lands somewhere between cabaret intimacy and comedy club energy. It's the type of Sunday night that reminds you why live performance matters, especially in a room full of people who get it.

Mike Flanagan's taking over the Post Office Cafe & Cabaret stage for Bear Hug, and you're in for a night of pure entertainment magic at one of Provincetown's most iconic venues. This isn't just a show—it's a celebration of community, talent, and the kind of energy that makes Bear Week unforgettable, all happening on the legendary cabaret stage that's been launching careers for nearly 50 years. Grab a craft cocktail, settle in, and get ready to be absolutely charmed by one of the best nights of the week.

Mike Flanagan takes over Town Hall for Bear Week 2026

Jeremiah Harmon returns to Provincetown for an intimate evening of story-songs and chamber pop rooted in folk blues and Southern gospel. Accompanied by a small string band and joined by special guests from the local scene, this is music drawn from family history and early childhood memory—the kind of performance that reminds you why people travel to hear artists like this.

Darren Criss brings his Tony Award-winning talent to an intimate solo evening at the historic Provincetown Town Hall. Expect a kaleidoscopic mix of Broadway favorites, timeless standards, and original pieces woven together with his signature humor and storytelling. This is the kind of rare, up-close performance that reminds you why his voice and artistry have captivated audiences across Glee, Broadway, and beyond.