The 10 best things to do in Outer Cape this weekend
October 23–25, 2026 · handpicked from everything on across Outer Cape.
Provincetown carries the weekend with drag brunches, cabaret, and piano bars, while Orleans and Wellfleet offer live music, a Halloween stroll, and library and gallery happenings. Friday through Sunday has plenty for a mix of nights out and slower daytime plans.
CROWN GHOULS: Drag Brunch – 10:30AM – Spooky BearSaturday · 10:30 AM · ProvincetownA Halloween drag brunch at the Crown & Anchor with CROWN GHOULS, a full singing-and-dancing show that makes for a lively Saturday late morning. The 10:30 AM seating is the earlier of the two.Dark Rooms:Jackie CoxSaturday · 7:00 PM · Red Room · ProvincetownJackie Cox returns to the Red Room with DARKROOMS, an adults-only cabaret billed as her filthiest yet. It's a sharp pick for a Saturday night out in Provincetown.Brittany & Clint – Piano BarSunday · 3:00 PM · ProvincetownBrittany Rolfs and Clint Mo... share a piano bar night at the Sunday evening slot, with Brittany billed as a Broadway-caliber vocalist. A good way to close the weekend.SOLID GOLD TEASunday · 4:00 PM · Boatslip Resort & Beach Club · ProvincetownDJ Maryalice spins 70s and 80s disco at the Boatslip on Sunday night, with a dress-up theme of sequins, satin, and bell-bottoms. Expect a fun, high-energy finish to the weekend.SIRENSFriday · 3:00 PM · ProvincetownThree local Provincetown singers, Marissa, Darlene and Lily Mae, share a night of live music on Friday. A low-key way to start the weekend in town.Johnny Spampinato & The Value LeadersFriday · 6:00 PM · Hog Island Beer Co. · OrleansJohnny Spampinato & The Value Leaders play Hog Island Beer Co. in Orleans on Friday, with food and drinks on site. A relaxed brewery night with live music.Front Street Jazz EnsembleSaturday · 1:00 PM · Parish Park · OrleansThe Front Street Jazz Ensemble plays danceable and listenable jazz at Parish Park in Orleans on Saturday evening. A good outdoor option if the weather holds.Halloween StrollSaturday · 3:00 PM · Main Street, Orleans, MA, USA · OrleansThe annual Halloween Stroll along Orleans Main Street is a family-friendly evening of candy, costumes, and seasonal fun on Saturday.So Percussion ConcertSaturday · 7:30 PM · Performing Arts Center, Brewster · EasthamGrammy-winning percussion quartet So Percussion performs at the Performing Arts Center in Brewster on Saturday night. A standout concert for fans of adventurous music.Roots: A Farm to Circus ShowSaturday · 1:00 PM · Payomet Performing Arts Center · TruroRoots: A Farm to Circus Show at the Payomet Performing Arts Center in Truro runs both Saturday and Sunday. A distinctive one-off show that suits a daytime or early evening outing.
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