The 12 best things to do in Outer Cape this weekend

October 16–18, 2026 · handpicked from everything on across Outer Cape.

Women's Week and Oyster Fest dominate the Outer Cape this weekend, bringing drag brunches and live comedy to Provincetown alongside a full celebration of shellfish culture in Wellfleet. Whether you're catching cabaret acts, live music at local breweries, or heading to the marina for oyster shucking, there's energy and flavor across the region.

25 Years “In Pursuit of the Groove: The Highs, The Lows, and The Original Music That Kept Them Standing."Friday · 3:30 PM · Red Room · ProvincetownSister Funk, the legendary all-female band, takes the stage for an intimate cabaret celebrating 25 years of groove and original music. A rare chance to experience this powerhouse in a close setting at the Red Room.THE BEST OF LEA DELARIA – FRI 16 – Women’s WeekFriday · 7:00 PM · Paramount · ProvincetownLea DeLaria brings slick jazz and outrageous comedy to the Paramount for Women's Week. She's as sharp and irreverent as ever—a Friday night highlight not to miss.Sophie B. HawkinsFriday · 7:30 PM · Provincetown Inn · ProvincetownGrammy-nominated Sophie B. Hawkins, known for 'Damn I Wish I Was Your Lover,' plays the Provincetown Inn Friday night. A rare headlining appearance from a '90s icon with real staying power.Crown Jewels – Drag Brunch 10:30 AM – Women’s WeekSaturday · 10:30 AM · ProvincetownCrown Jewels is Provincetown's all-singing, all-dancing drag brunch with Delta Miles, Roxy Pops, and Qya Cristal. Two seatings Saturday—10:30 AM and 1 PM—let you pick your timing for this fabulous Women's Week staple.THE PLAYMATES: CALLING ALL COWGIRLS – Women’s WeekSaturday · 4:00 PM · ProvincetownThe Playmates, a Nashville-based female acoustic duo, blend folk-rock, country, and originals with rich harmonies on Saturday at the Crown & Anchor. Award-winning songwriter Jess Leary leads a warm, intimate set.Wellfleet Oyster FestSaturday · 12:00 AM · Wellfleet, MA · WellfleetWellfleet OysterFest is the Cape's marquee fall festival, featuring a raw bar, live music, kids' activities, local vendors, and the famous oyster shuck-off. It's a full day of food, fun, and community pride in the region's signature shellfish.Oyster Fest Saturday Special! Live Jazz with the Salt Marsh Jazz QuartetSaturday · 3:00 PM · The Wicked Oyster · WellfleetAfter OysterFest Saturday, settle into dinner at the Wicked Oyster with the Salt Marsh Jazz Quartet. Local live jazz paired with fresh seafood is a perfect post-fest wind-down.Paula ColeSaturday · 8:00 PM · Provincetown Inn · ProvincetownPaula Cole, Grammy Award winner behind hits like 'Where Have All the Cowboys Gone?' and 'I Don't Want to Wait,' closes the Mayflower Series at the Provincetown Inn Saturday night. A significant artist in her own right.The Grab Brothers FULL BANDFriday · 3:00 PM · Wellfleet Pearl · WellfleetThe Grab Brothers full band kicks off Friday at Wellfleet Pearl with a mix of Boston energy and Americana—Larry and Marc Grab bring multi-instrumental versatility and genuine warmth to the stage.Full Moon SomewhereSaturday · 3:00 PM · Wellfleet Pearl · WellfleetFull Moon Somewhere, a Boston-based power trio, plays Saturday at Wellfleet Pearl with rock, pop, country, folk, and traditional Irish music. Barry Hynes (of Shoot The Moon) leads a band that spans genres with ease.Creare Symphonia in ConcertSunday · 3:30 PM · Performing Arts Center, Brewster · EasthamCreare Symphonia performs Vaughan Williams' The Lark Ascending and Finzi's music for Shakespeare Sunday at the Brewster Performing Arts Center. English 20th-century classics rendered in autumn light.Small Mouth SoundsSunday · 2:00 PM · Provincetown Theater · ProvincetownSmall Mouth Sounds, the wordless theatrical comedy that's taken the country by storm, plays Provincetown Theater through the weekend. Pure physical comedy and charm—no dialogue required.

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