The 12 best things to do in Outer Cape this weekend
August 7–9, 2026 · handpicked from everything on across Outer Cape.
Sunday on the Outer Cape leans hard into cabaret, drag, and live music — Provincetown alone offers a Sasha Colby pool party, a Post Office Café double bill, and Dina Martina's singular brand of chaos — while music and theater spread out from Truro's vineyards to the Wellfleet Pearl, Brewster's chamber stage, and Orleans.
SASS with SASHA COLBY – Pool PartySunday · 8:00 AM · ProvincetownRuPaul's Drag Race Season 15 winner and Miss Continental legend Sasha Colby headlines this poolside benefit for Summer of Sass, with music from P-town favorite KT.Drag BrunchSunday · 11:00 AM · Post Office Cafe & Cabaret · ProvincetownSome of Provincetown's finest drag entertainers take the stage for lip-syncs and laughs at this long-running Post Office Café brunch tradition.Hey Bitch!Sunday · 7:00 PM · Post Office Cafe & Cabaret · ProvincetownQueer icon Bitch (of Bitch and Animal) brings her wild musical memoir — feminist awakening, indie rock stardom, and all — to the Post Office Café cabaret stage.AN EVENING WITH JOY BEHAR & JUDY GOLDSunday · 7:00 PM · ProvincetownThe View's Emmy-winning co-host Joy Behar sits down with fellow comedian Judy Gold for a night of conversation and laughs at Ptown Town Hall.ABSOLUTE DINA MARTINASunday · 6:00 PM · Crown & AnchorCult cabaret figure Dina Martina brings her singular blend of song and delightful bewilderment to Crown & Anchor.Patty Larkin & Lucy KaplanskySunday · 6:00 PM · Payomet Performing Arts Center · TruroTwo celebrated singer-songwriters, Patty Larkin and Lucy Kaplansky, share the Payomet stage for an evening of folk craftsmanship in Truro.Mr. Gotcha!Sunday · 3:00 PM · Wellfleet Pearl · WellfleetThis high-energy Cape Cod band turns the Wellfleet Pearl into a dance floor with a set spanning rock, funk, soul, and dance favorites.Consonare Chamber Players in ConcertSunday · 7:30 PM · Arts Empowering Life Inc. · BrewsterThe Consonare Chamber Players close out their Brewster concerts with piano quintets by Florence Price and Amy Beach — a chance to hear both American composers side by side.Summer in the City: the Circus that Never SleepsSunday · 4:00 PM · Cirque by the Sea at WHAT · WellfleetWHAT's Cirque by the Sea brings acrobatics and spectacle under the open sky in Wellfleet with this touring circus production.Sunday FundaySunday · 5:30 PM · Truro Vineyards of Cape Cod · TruroTruro Vineyards keeps things easy with DJ Emerson, a food truck, and an ice cream truck — no reservations needed, just wander in.Girl from the North CountrySunday · 2:00 PM · All performances will be in Cape Rep’s Indoor Theater · EasthamCape Rep stages Conor McPherson's Depression-era drama set to the songs of Bob Dylan in their intimate indoor theater in Eastham.Disney's DescendantsSunday · 2:00 PM · The Academy of Performing Arts · OrleansThe Academy of Performing Arts brings Disney's hit musical about the teenage children of Maleficent, the Evil Queen, Jafar, and Cruella de Vil to the Orleans stage.
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