The 10 best things to do in Outer Cape this weekend

August 21–23, 2026 · handpicked from everything on across Outer Cape.

Late August on the Outer Cape leans hard into cabaret and drag, with Provincetown hosting a run of headline queens alongside touring rock and folk acts up the coast, while Orleans wraps its craft-fair season and Truro keeps the vineyard party going.

Jackie Cox: Beam Me Up Jackie!Sunday · 7:00 PM · Red Room · ProvincetownRuPaul's Drag Race alum Jackie Cox, the self-proclaimed "Persian Princess of Drag," brings a new show to the Red Room — a reliable spot for big-personality drag with a devoted following.LATRICE ROYALESunday · 7:30 PM · Show Room · ProvincetownLatrice Royale headlines the Show Room, a rare chance to catch one of drag's most beloved and warmest performers in an intimate P-town room.Judy Gold - Call of JudySunday · 8:30 PM · Post Office Cafe & Cabaret · ProvincetownComedian Judy Gold marks her 35th year performing at the Post Office Cabaret with Call of Judy, her signature blend of sharp stand-up and free-speech-fueled storytelling.MELISSA ERRICO w/ BILLY STRITCH in THE STREISAND EFFECTSunday · 8:30 PM · ProvincetownTony nominee Melissa Errico teams up with Billy Stritch for The Streisand Effect, a Provincetown Theater show built around her singing Barbra — a good pick if you want polished vocal cabaret over drag or comedy.THE REAL HOUSEWIVES OF TEA DANCESunday · 4:00 PM · Boatslip Resort & Beach Club · ProvincetownThe Boatslip's Sunday tea dance goes full Real Housewives with DJ Maryalice at the helm — dress for drama and expect the deck to be packed.Nauset Summer Craft FestivalSunday · 10:00 AM · Nauset Regional Middle School · OrleansThis juried outdoor craft festival at Nauset Regional Middle School wraps its two-day run with American-made crafts, art, and specialty foods — an easy, low-key way to spend a late-summer afternoon.The Samples LIVE at Hog Island Beer Co.Sunday · 10:00 PM · Hog Island Beer Co. · OrleansColorado road-trip band The Samples make a one-night stop at Hog Island Beer Co., a solid excuse to catch touring live music with a beer in hand on the patio.Cheap VoovaSunday · 3:00 PM · Wellfleet Pearl · WellfleetCheap Voova, a Cape and South Shore fixture for over 25 years, plays the Wellfleet Pearl — dependable bar-band energy from a group that's been doing this since 1995.Back in the Saddle – Burlesque!Sunday · 7:00 PM · Payomet Performing Arts Center · TruroPayomet Performing Arts Center in Truro hosts a burlesque cabaret night, a good option if you want a theatrical, adults-only alternative to the drag-heavy P-town lineup.Girl from the North CountrySunday · 7:30 PM · Cape Rep Theatre · East BrewsterCape Rep Theatre continues its season with Girl from the North Country, the Conor McPherson play set to Bob Dylan's music and lyrics — a distinctive theatrical pick for anyone craving something other than drag or comedy this weekend.

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