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Cape Cod Events Calendar

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Cape Cod offers more than world famous beaches. Whether you are looking for something to do today, this weekend or planning an itinerary for an upcoming vacation, there's something for everyone to find and explore!

Looking for Martha's Vineyard or Nantucket events? View these calendars: Martha's Vineyard events and Nantucket events.

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View events on Cape Cod on or after 9/18/2025

11th Annual Vinegrass Music Festival

Where: Truro Vineyards, 11 Shore Rd., Truro

When:

How Much: $55

Categories: Music

The Vinegrass festival will feature (4) nationally touring bands on the main stage, and several regional musicians on the pavilion stage. The eclectic mix of music, steeped in the Americana & Bluegrass styles, will showcase innovative songwriting, musicians who have mas...read more

Nauset Youth Alliance "The Bash" Fundraiser

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

When:

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

Bonsai Workshop at High Limb Cider

Where: High Limb Cider, Village West Shopping Center, Carver Rd, Plymouth

When:

How Much: $85

Categories: Arts

Beginner workshops are perfect for you to grab your friends, grab a drink and come make tiny trees! We're bringing the awesome art of bonsai out of the hedged in gardens and into the streets! Or at least into your favorite bars/breweries/pubs. Bonsai Bar is a night of f...read more

Brewster's Historic Main Street Walking Tour

Where: Meet at , 1993 Main St, Brewster

When:

How Much: $15, $12members/15 non-members

Categories: Historical

Join us for an hour-long journey through history along Brewster's iconic Main Street, also known as the Old Kings Highway! Take a step back in time as our guide leads you through this charming street, brimming with stories of brave sea captains, antique homes, and long-...read more

Outermost Friday Market in the Park

Where: The Village Green, Orleans

When:

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.

Annual Yarmouth Seaside Festival

Where: Joshua Sears Memorial Field, 1175 Rt. 28 South, Yarmouth

When:
Sunday, October 12, 2025,
Monday, October 13, 2025,

How Much: Free

Categories: Festival

The Festival features a huge Arts & Craft Show that brings crafters from all over New England, great food, live music, children’s entertainment tent, games and rides, and much more. Over 125 juried craft people present a wide variety of beautiful and unique items rangin...read more

Sandwich Glass Museum Annual PumpkinFest

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

When: -

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

Outermost Roots & Blues Festival

Where: Nauset Beach, Orleans

When: -

How Much: Adults $208, Children $59, Tickets range from $59-$342

Categories: Music

The Outermost Roots & Blues Festival is a celebration of roots, blues, Americana, and folk music, bringing together national touring acts and regional talent for a day of live performances, food, drinks, and community on the Cape. Join us on Nauset Beach for this epic e...read more

Cape Cod Marathon

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

When: -

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: -

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


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