The 11 best things to do in Outer Cape this weekend

September 18–20, 2026 · handpicked from everything on across Outer Cape.

This weekend the Outer Cape leans hard into cabaret and drag, with Provincetown's clubs in full swing alongside a strong slate of live music from Wellfleet to Truro and Orleans.

DIVA!: "3 Times A Broad"Saturday · 7:00 PM · Post Office Cafe & Cabaret · ProvincetownProvincetown favorites Delta Miles, Qya Cristál, and Roxy Pops return to the Post Office Cabaret for the fourth year of this live-singing drag spectacular, now retitled "3 Times A Broad."ABSOLUTE DINA MARTINASaturday · 6:00 PM · Crown & Anchor · ProvincetownAbsolute Dina Martina brings her singular brand of deadpan comedy to the Crown & Anchor for a late-night Saturday show.PIANO BAR - Brittany Rolfs and Chris GrassoSaturday · 7:00 PM · Pilgrim House · ProvincetownBrittany Rolfs and Chris Grasso team up for Pilgrim House's Piano Bar, a laid-back spot to catch two skilled performers trade songs at the keys.NOW THAT'S WHAT I CALL DRAG BRUNCHSunday · 11:00 AM · Show Room · ProvincetownSunday brings another round of the Show Room's drag brunch, a reliably lively way to start the day in Provincetown.Isabelle O'Connell in ConcertSaturday · 7:00 PM · Wellfleet Preservation Hall · WellfleetInternationally acclaimed pianist Isabelle O'Connell performs music from her new solo album Cocteau at Wellfleet Preservation Hall, exploring musical connections in a rare solo recital.Johnny and the Value LeadersSaturday · 3:00 PM · Wellfleet Pearl · WellfleetThe Value Leaders bring their raw, high-energy rock 'n' roll to Wellfleet Pearl, a good pick if you like NRBQ, the Spampinato Brothers, or the Incredible Casuals.Wellfleet Gallery StrollSaturday · 5:00 PM · Wellfleet Cultural District · WellfleetWellfleet's galleries throw open their doors for Saturday evening receptions and extended hours across the Cultural District, an easy way to wander and see what's new.BIKEMANSunday · 3:00 PM · Wellfleet Harbor Actors Theater · WellfleetThomas F. Flynn's BIKEMAN gets a Sunday matinee performance at Wellfleet Harbor Actors Theater.Josh Ritter: A Book Of Gold Thrown OpenSaturday · 7:00 PM · Payomet Performing Arts Center · TruroJosh Ritter brings his songwriting to Payomet Performing Arts Center in Truro for "A Book Of Gold Thrown Open," a headline-caliber show worth planning around.Power LoadSaturday · 2:00 PM · Hog Island Beer Co. · OrleansPowerload tears through a night of AC/DC favorites at Hog Island Beer Co. in Orleans, the kind of loud, riff-heavy set that turns a brewery into a rock show.Cape Symphony Presents: Hot Tamale Brass BandSunday · 12:30 PM · Aplaya Kitchen + Tiki Bar · OrleansCape Symphony presents the Hot Tamale Brass Band at Aplaya Kitchen + Tiki Bar in Orleans, a fun way to close the weekend with some brass-driven energy.

Looking for the current weekend? See what’s on in Outer Cape this weekend →