^{Valerie June will be onstage at Payomet.}

2026 Entertainment Season Preview

by Steve Desroches

Several years ago, the Merriam-Webster dictionary named “authentic” the word of the year, and that word continues to be one of the top Internet searches, not just in English, but also its translation into a variety of languages. It’s no wonder. The world can be a complicated and confusing place. With so many deliberate misinformation campaigns, corporate gobbledygook, Internet bots and trolls, and social media companies fueling outrage things are bad enough, but now AI, ChatGPT, fake videos, and questionable bylines that blur the lines between real reporting and just jazzing up press releases create further mistrust of journalism. These days it can be hard to differentiate what is real and what is manufactured and manipulated. That is why now, more than ever, Provincetown and the Outer Cape are so important. Here you still find original ideas, imagination and curiosity, risk and experimentation. Provincetown is the real deal. Even though private equity, uninspired chains, and corporate giants come knocking, the art colony and the creative community-at-large is so powerful as to overcome attempts at censorship, suburbanization, or uniformity. And in large part, it’s because of the support of the residents of Provincetown and the thousands who visit who take none of it for granted. 

Come June, Provincetown Magazine will present our annual Art Gallery Season Preview outlining the artists and their work that will be presented this year, which is always a remarkable offering and reminder of the art that is created here. As is tradition, this Memorial Day issue, we present a large sampling of who will grace the many stages of the Outer Cape as it becomes a veritable summer-long fringe festival, especially in Provincetown. In a world that can feel increasingly virtual instead of visceral, lived through small screens and robot voices, attending a live performance experienced with others creating an audience is good for the culture, the economy, and the soul. Every ticket you buy supports not only those on stage and the venue, but a grand tradition that is over a century old and continues to thrive.

Art House

There are some changes over at the Art House as Kevin Levesque and Prescott Seymour, perhaps better known as Miss Conception and Sutton Lee Seymour, respectively, take over as producing partners. Miss Conception presents Scream Kween a drag homage to the best of horror films while Seymour gives us Super-Ma’am: Saving the World is a Drag, as she transforms into a drag superhero. Both shows run now through September 12. Provincetown’s own burlesque star, Spookey returns with his Helltown Burlesque (now through September 11) featuring a rotating cast of guest stars performing aerial acrobatics, pole dancing, drag, and more. Beatrix Eglantine Aurthurson goes on a deep-sea dive with Call Me Ursula (now through August 26) a show all about the delicious villain from Disney’s The Little Mermaid. Dancing drag superstar Edie returns with an update of last summer’s smash hit live gameshow, Are You Smarter Than a Drag Queen (July 2 – September 13), a stars-and-stripes edition as it celebrates America’s 250th birthday.  And speaking of hit shows, the fellas from Puppetry of the Penis (now through September 13) swing back into town with their genital origami. In addition to their summer headliners, the Art House also welcomes guest spots throughout the season with showtune songster Seth Sikes (August 16 and 18), vocal powerhouse Hilarie Tamar (July 23 and 26, August 16 and 27), rock-and-roll drag queen Jizzelle (July 7 and 9, August 29 and 30), the wonderfully blonde Scarlett Strauss (July 5 and 12, August 2 and 6) with Trannah Montana, and global vagabond musician Zoe Lewis (July 28
and August 9).

Crown & Anchor

From the sounds of hammers and saws it’s clear that the Crown & Anchor is going through a major transformation. Recently purchased by Tryst Hospitality, founded by Tristan Schukraft, an LGBTQ travel and nightlife company, the Crown & Anchor joins LGBTQ hotels and nightclubs in Tryst’s portfolio in Fire Island, Rio de Janeiro, Puerto Vallarta, San Juan, Wilton Manors, and Chicago, as well as The Abbey in West Hollywood. The closing date on the Crown & Anchor took five months longer to achieve than previously planned and, as such, the iconic party palace will do a phased re-opening throughout the summer. 

While the hotel portion will not operate this season, as the rooms are all undergoing major renovations, Paramount, the Vault, the Courtyard, the Wave Bar (including Sundays and Wednesdays with Tom Yaz) will all be open this Memorial Day weekend. And come mid-June drag favorite Varla Jean Merman, Dina Martina, and Tina Burner all return to the Crown for summer-long runs as will piano man Jon Richardson, gorgeous vocalist Qya Cristal backed-up by the Bart Weisman Trio, and Broadway great James Jackson, Jr. And Ryan Landry’s Showgirls opens at the Crown on June 15 before heading back to the Provincetown Inn where it will be every Monday night throughout the summer.  Stay tuned for more news from the Crown & Anchor as well as a fully operational Provincetown staple come 2027.

Great Music Provincetown

Now entering its 28th season what was Great Music on Sundays @ 5 is now Great Music Provincetown as it expands to offer concerts on Saturday as well at the Unitarian Universalist Meetinghouse. Produced by musician John Thomas the series opens on June 21 with 1930s Radio Show Live! featuring Jo Brisbane, Arian Carlos, Marcy Feller, Loren Lee, Paige O’Connor, Mozelle, Fermín Rojas, Hilarie Tamar, Eric Auger, Sam Sewell, and John Thomas. Broadway-themed concerts are presented on Sundays (August 2, 16, 30) and an international offering titled Music Without Borders is on Saturday (July 11 and 25, August 8 and 22). The Great Music Provincetown series goes through September and closes with a special holiday concert during Holly Folly, the first weekend in December.

Gifford House

The Gifford House has sat atop Mill Hill for over 140 years, and over this past winter the hot spot on Carver Street got a makeover with a major external renovation. The Wilde Playhouse once again is a performance space home to some of the most innovative and unconventional acts in town. The theatrical wunderkind Cody Sullivan continues his wildly popular Cody Plays every Monday on into the autumn, in which he and a rotating guest cast perform a play created in a day. Yaron Spiwak and Josie James present You’ve Got a Friend (July 9 – August 20), a tribute to James Taylor and Carole King. Singer-songwriter Matthew Darren (July 17) returns for Bear Week, RuPaul’s Drag Race superstar Raja (June 19 – 20) takes to the Wilde as do stand-up comedians Jake Cornell (June 21) and Conor Janda (June 25), performance artist Jibz Cameron (June 26), The Duchess Improv (July 21 – 24) from New York City,  the World’s Most Interesting Sisters (July 29 – 30) a drag comedy hour featuring musical parodies, and drag firecracker Marti Gould Cummings (September 3 – 4). 

The Love Lounge hosts music nightly throughout the summer including Lily Mae Harrington (Monday), Hilarie Tamar and Peter Toto (Tuesday), Tori McClain and Chris Grasso (Wednesday), Brittany Rolfs and Clint Morris (Thursday), Liza Lott and Yaron Spiwak (Friday) James Jackson, Jr. (Sunday) with Saturday nights a wild card of special guests.

Harbor Stage Company

While sadly the Wellfleet Harbor Actors Theater (WHAT) cancelled their 2026 due to financial issues, the dynamic Harbor Stage Company is always a great reason to visit the small theater down by the harbor. The season opens with Prize Fight (June 18 – July 11) a new play by Brenda Withers about an uncompromising writer who wants to refuse a distinguished award while their silver-tongued agent must convince them to choose prestige over principle. Next is Agatha Christie’s The Mousetrap (July 16 – August 8), a classic in which eight strangers are trapped in a blizzard and race to solve a desperate puzzle; who among them is behind a twisted killing spree and who might be the next victim? And closing out the season is The Realistic Jonses (August 13 – September 4) by Will Eno. In this contemporary play two sets of suburban neighbors navigate marriage, mortality, and midlife melancholy in this delicately dark comedy.

Payomet Performing Arts Center

Want a break from the hustle and bustle of Provincetown? Head over to the Payomet Performing Arts Center in North Truro to enjoy music under their seasonal tent at the old Air Force base. Payomet brings a wide array of performers and a diverse offering of musical styles including Cécile McLorin Salvant (June 14), who blends jazz, blues, folk, and baroque music, reggae legends Black Uhuru (June 19), the Cape Cod Women’s Music Festival (June 27), the legendary Mavis Staples (July 9), the always hilarious Paula Poundstone (July 11), singer-songwriter Martin Sexton (July 17), Los Lobos (July 24), masterful songwriter Dar Williams (July 29), guitar virtuoso Duane Betts and Palmetto Motel (July 30), comedian and late night talk show host Seth Meyers (August 2), Ukrainian traditional music performers DakhaBrakha (August 5), Patty Larkin and Lucy Kaplansky (August 9), and the psychedelic folk of Valerie June (August 30).

Pilgrim House

Starting the 2026 season with new management, Pilgrim House has scheduled an expanded offering of entertainment brining back long-time favorites and inviting a slew of performers to town for their Provincetown debut. A hilarious twofer kicks off the summer when actor and comedian Joel Kim Booster (June 26 – 27) and Emmy and Golden Globe-winning comedian Guy Branum (June 5 – 7) hit the storied stage at Pilgrim House. A peppering of some of the best from RuPaul’s Drag Race spices things up asPlasma (June 4 – 17, June 23 – July 1) brings her Bernadette Petters show to the P House followed by Latrice Royale (July 2 – September 5) in her first full summer run, and Provincetown favorite Sapphira Cristal (July 16 – August 19) in Mother Knows Breast. And speaking of drag legends, Anita Cocktail has a new home at Pilgrim House where she’ll present Anita Cocktail’s Variety Hour (now through August 29) every Saturday night. 

The dunes are alive with the sound of music as The Stephens: Sondheim & Schwartz: A Broadway Cabaret (June 28) celebrates these two musical giants and Broadway Supper Club (now through August 31) hosted by Brittany Rolfs and Marissa Miller takes over the newly renovated front room every Monday night. Music and comedy meld in Vexed (now through September 7) a wickedly funny Broadway-inspired parody musical that gives a Sapphic twist to Wicked, written, produced, and starring Tori McClain. And the laughs keep coming when the devastatingly funny Liza Treyger (July 23 – 26) makes her Provincetown debut and the hilarious Roz Hernandez (August 26 – September 7) returns.

Post Office Café and Cabaret

The funky and fun attic theater the Post Office Cabaret has been a staple of the Provincetown performance scene for over 50 years. And this summer they build on that legacy with a packed schedule that includes the dynamic and daring queens of Diva!, with Qya Cristal, Delta Miles, and Roxy Pops (now through September 2) in an all-new show featuring all live vocals. The iconic Illusions (June 30 – August 25) returns with Billie Jean and Lakia Mondale presenting glamorous classic drag, and after an impressive Provincetown-debut, A Woman Named Carlos (now through September 12) returns for another full season with her modern take on classic drag. The Showbiz Spitfire Paige Turner (now through September 2) brings Drag Me to the Movies with her take on Hollywood. Provincetown legend Miss Richfield 1981 (now through September 19) performs her carpe-diem-inspired show, You Can’t Have Ice Cream When You’re Dead. 

Also at the P.O. is feminist indie rocker Bitch (now through September 13), Emmy-winning comic Judy Gold (now through September 13), RuPaul’s Drag Race sweetheart Nina West (May 28 – August 25) with her Oh, Mary! spoof Oh, Scary! Comedic playwright Jamie Morris is reviving a trio of his clever and campy plays with The Devil Wears Payless (now through September 13), The Golden Mean Girls (June 26 – September 11), and Shartt$ Creek (July 1 – September 9). And in the realm of theatrical comedies, Sabrina the Middle Aged Witch (May 29 – October 10) flies back into town to do battle with menopause. Stephen Colbert was forced off of late -night television, but Bob Keary returns with his live talk show Goodnight Provincetown (June 29, September 28, and October 26). And in the realm of music, Tianna Esperanza (May 31 – July 26) present her smooth as velvet stylings while the always amazing singer-songwriter Matt Alber (July 12 – 13) comes to town for Bear Week and Australian neo-cabaret star Kim David Smith (August 13) presents some torch songs for tough times.

Provincetown Town Hall

With 700-plus seats the historic auditorium in Provincetown Town Hall is the largest venue on the Outer Cape and as such hosts the biggest acts to come our way earning the nickname of Provincetown’s Carnegie Hall. Independent production organizations and smaller venues use Town Hall to bring in an array of stars. This summer Payomet Performing Arts Center continues their Provincetown Road Show series with the Talking Heads tribute band Start Making Sense (June 20), the Pope of Trash John Waters with Going to Extremes (July 23), hilarious stand-up comic and actress Robby Hoffman (July 25), Almost Queen: A Tribute to Queen (August 1), fabulous comedian Matteo Lane (August 7 – 8), and RuPaul’s Drag Race sensation Bob the Drag Queen (August 22).

Mark Cortale continues his Town Hall series with Broadway’s Megan Hilty (July 5), RuPaul’s Drag Race dynamo Alyssa Edwards (July 12), the devastatingly handsome and talented Cheyenne Jackson (August 2), the comedic duo of Joy Behar and Judy Gold (August 9), the wonderfully insulting comedy of Bianca Del Rio (August 16), the beautiful voice of Melissa Errico (August 23), and the indefatigable Marilyn Maye (August 30) who takes to the stage at age 98.

The Provincetown Portuguese Festival presents a fado concert (June 27) featuring masters of what is sometimes called the “Portuguese blues” and music man Mike Flanagan (July 16) takes over during Bear Week for another night of special guests and sounds to blow the roof off of the place. Funny man David Sedaris (August 5) returns to town and the Provincetown Business Guild brings the fab glam rock band Tony and the Kiki (August 19) to town as the Carnival headliners performing the night before the parade.

Tin Pan Alley

Tin Pan Alley is the musical Cheers of Provincetown. A place where everybody knows your name and invites you to pull up a seat and listen to some of the best musicians and singers Provincetown has to offer. All summer long Tin Pan Alley will host a variety of people tickling the ivories and belting out high notes including, Mike Flanagan, Peter Toto, Clint Morris, Jizzelle, Jacob Glass, Jim Brosseau, Michael Ryan, Kyle Broady,Frankie Campofelice, Robbie Pate, Dicky Ryan, Sarah Glassman, and more. All are on rotating schedules so check Provincetown Magazine’s Happenings section each week or just drop in as all are fabulous.

Provincetown Theater

The Provincetown Theater continues to flourish and shine as its stature grows to being a regional theatrical force. After the current production of Landford Wilson’s Fifth of July closes on May 31, the theater welcomes Cody Sullivan with his new play AUTOCRAT Inc., a madcap tale about two sets of twins and the tumultuous sale of the Autocrat Coffee Syrup company to Amazon, every Tuesday in June. And June also is home to the 4-Star Solo Show Festival presenting Prisontown by Lee Osorio (June 4 – 6), Beth by Marty Miller (June 11 – 13), Black Bastard by Jon Gentry (June 18 – June 20), Fair State by Megan Gogerty (June 25 – June 27). After selling out its October run in less than 24 hours, the Provincetown Theater is bringing back Jon Richardson’s musical The Jack of Hearts Club (July 16 – September 6), a veritable love letter to Provincetown set in a gay bar at the end of summer in 1963. 

Red Room

The hip and funky Red Room, with its intimate cabaret stage and larger Saki Stage, keeps summer sizzling with the fantastically vulgar Sherry Vine (June 10 – 12), the dynamic legend Candis Cayne (June 16 – 18), and the wonderfully off-the-wall Tammie Brown (June 17 – September 13), who offers her summer run of Bonkerz! and a special July performance of Tammie Brown’s Christmas in July (July 3 – 31), and Jackie Cox ( July 1 – September 13) goes intergalactic with Beam Me Up, Jackie. The stars of the new drag disaster spoof comedy, Stop! That! Train! Ginger Minj and Jujubee turn their attention to a different film with their spoof on Wicked, Licked for Gay (July 9 – July 26). 

The Red Room is the place to be for comedy with Tim Benzie’s Solve-Along-A-Murder-She-Wrote (June 27) where he plays a burly Jessica Fletcher who needs your help in solving a murder in Provincetown, the uber-funny stand-up comic Dylan Adler (July 2), Provincetown favorites Poppy Champlin (July 24 – July 26) and Suzanne Westenhoefer (July 24 – 26) come for GirlSplash, and the musical hilarity of Broadway Barbara Live! (July 21 – 25) keeps the laughs going as does comic Cheril Vendetti (August 7 – 8) and Alison Arngrim (August 4 – 6) with her bust-a-gut funny tell-all Confessions of a Prairie Bitch about her time as the villain Nellie Oleson on Little House on the Prairie. RuPaul’s Drag Race star Alexis Michelle (August 20 – 21, September 2) comes to town for a special Carnival Week appearance. And the Lucky Devil Theater Company presents their latest spoof I Know Who You Did Last Summer (July 5 – August 30) starring Liza Lott, Raquel Blake, and Mark Meehan every Sunday this summer.

For Tickets & Information

PROVINCETOWN

THE ART HOUSE thearthouseptown.com 214 Commercial St.
CROWN AND ANCHOR onlyatthecrown.com 247 Commercial St.
GIFFORD HOUSE giffordsprovincetown.com 9 Carver St.
GREAT MUSIC PROVINCETOWN ptownmusic.com 236 Commercial St.
MARK CORTALE at TOWN HALL ptowntownhall.com 260 Commercial St.
PILGRIM HOUSE pilgrimhouseptown.com 336 Commercial St.
THE POST OFFICE CABARET postofficecafe.net 303 Commercial St.
THE PROVINCETOWN THEATER provincetowntheater.org 238 Bradford St.
RED ROOM redroom.club 259 Commercial St.
TIN PAN ALLEY tinpanalleyptown.com 269 Commercial St.

NORTH TRURO

PAYOMET PERFORMING ARTS CENTER payomet.org 29 Old Dewline Rd.

WELLFLEET

HARBOR STAGE COMPANY harborstage.org 15 Kendrick Ave.

Theme Weeks & Special Events

Womxn of Color Weekend, June 3 – 8
Provincetown Pride, June 4 – 7
CabaretFest, June 8 – 14
Provincetown International Film Festival, June 10 – 14
Frolic: Men of Color Weekend, June 17 – 22
Juneteenth Celebrations, June 19
Provincetown Portuguese Festival, June 26 – 28
Independence Day Fireworks and Parade, July 4
Bear Week, July 11 – 18
Girl Splash, July 22 – 25
Family Week, July 25 – August 1
Jamaican Independence Day,  August 6
Provincetown Jazz Festival, August 11
Carnival Week, August 15 – 22
48th Annual Carnival Parade, August 20