Cape Cod Events 2026

View events on Cape Cod on or after 07/22/2018

Nauset Youth Alliance "The Bash" Fundraiser

Where: The Pelham House, 14 Sea St., Dennis

When: Sunday, October 5, 2025, 4:00 PM - 7:00 PM

How Much: $35, 21+ Event

Categories: Arts

Join Us for an Exciting Fundraiser!We are thrilled to announce our third BASH!, dedicated to supporting the Brewster Recreation and Nauset Youth Alliance Scholarship Programs. Your participation not only promises a fantastic experience but also plays a crucial role in m...read more

Tuesday Talks: Derek Bartlett: Haunted Cape Cod

Where: Atwood Museum, 347 Stage Harbor Rd. PB 709, Chatham

When: Tuesday, October 7, 2025, 5:00 PM - 6:00 PM

How Much: $10, Free for members

Categories: Holiday

Join us for our October 'Tuesday Talks' lecture on Tuesday, 10/07, at 5pm with Derek Bartlett. Derek will regale us with spooky tales of haunted happenings, stories, and locations of people and places around Cape Cod. He will tell us about his work as a tour guide and r...read more

Outermost Friday Market in the Park

Where: The Village Green, Orleans

When: Friday, October 10, 2025, 1:00 PM

How Much: Free

Categories: Festival

The Orleans Chamber of Commerce will host Outermost Friday in the Park on the village green at the corner of Main Street and Route 28. The free event will feature live music, DJs, food trucks, beer and wine and more than 30 local merchants and nonprofit groups.

Sandwich Glass Museum Annual PumpkinFest

Where: Sandwich Glass Museum, 129 Main St., Sandwich

When: Saturday, October 11, 2025 10:00 AM - Sunday, October 12, 2025 2:00 PM

How Much: Adults $12, Children $2, $11 Seniors, $11 retired Military, Free $0 active Military -Mass. Teachers’ Association

Categories: Festival

Fall has arrived! Join us at the Annual PumpkinFest to be held on the grounds of the Sandwich Glass Museum. Each year the Sandwich Glass Museum challenges local glass artists to craft one-of-a-kind or limited edition creations. Ranging from the petite to large scale an...read more

Cape Cod Marathon

Where: Cape Cod Running Club, 661 Main St, Falmouth

When: Saturday, October 11, 2025 - Sunday, October 12, 2025

How Much: Free

Categories: Sports

The 2025 Cape Cod Marathon Weekend will take place on October 11 & 12.

PumpkinFest

Where: Sandwich Glass Museum, 129 Main Street, Sandwich

When: Saturday, October 11, 2025 10:00 AM - Sunday, October 12, 2025 2:00 PM

How Much: Free

Categories: Festival

Our original and best outdoor festival fundraiser retail event of the year. Featuring glass pumpkins and other Autumn / Halloween themed handblown glass artwork from local and regional studio glass artists. Admission is free.Event will be held both Saturday and Sunday u...read more

Indigenous Peoples' Day: Film Screening: We Still Live Here - Âs Nutayuneân, by Anne Makep

Where: Atwood Museum, 347 Stage Harbor Rd. PB 709, Chatham

When: Saturday, October 11, 2025, 10:00 AM - 4:00 PM

How Much: Free

Categories: Film

Join us on Saturday, October 11th, to learn and listen during the Atwood Museum's Indigenous Peoples' Day Film Screening of We Still Live Here – Âs Nutayuneân, a documentary by Anne Makepeace about the incredible revival of the Wampanoag language. The film wil...read more

Live Music every Tuesday at the Wicked Oyster!

Where: The Wicked Oyster , 50 Main Street, Wellfleet

When: Tuesday, October 28, 2025, 6:00 PM

How Much: Free

Categories: Music

Join the Wicked Oyster team for live tunes every Tuesday, Thursday, and Saturday in October! On Tuesday's, Duo Mike Flanagan & Todd Baker alto sax/ double bass will take the stage for an, "adventurous musical ride," performing a range of styles, weaving through genres w...read more

Live Music every Thursday at the Wicked Oyster!

Where: The Wicked Oyster , 50 Main Street, Wellfleet

When: Thursday, October 30, 2025, 6:00 PM

How Much: Free

Categories: Music

Join the Wicked Oyster team for live tunes every Tuesday, Thursday, and Saturday in October! On Thursday's, The Volunteers / Quartet take over with Alex Hay on percussion, Rod McCaulley double bass, Asa Naduea on guitar and Andrew Staker on tenor sax. See the link below...read more

Live Music every Saturday at the Wicked Oyster!

Where: 50 Main Street, Wellfleet

When: Saturday, October 25, 2025, 6:00 PM

How Much: Free

Categories: Music

Join the Wicked Oyster team for live tunes every Tuesday, Thursday, and Saturday in October! Saturday's are a wildcard with rotating guest talent including Mozelle Andrulot, Mike Flanagan, and more. See the link below for reservations, as they are required for entry!