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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 3/31/2025

Pumpkin People in the Park

Where: Kate Gould Park, Main Street and Beyond, Chatham

When: Daily, -

How Much: Free

Categories: Festival

Pumpkin People in the Park can be found in Kate Gould Park and the bandstand on Main Street. The creative and innovative Pumpkin People are fashioned by local businesses, organizations or just plain folk. They are on display from October 14-31! Come and see these outr...read more

Wellfleet OysterFest 2025

Where: Downtown Wellfleet, 300 Main St., Wellfleet

When: Daily, -

How Much: $20, Varies

Categories: Festival

The Wellfleet OysterFest will take place the weekend of Saturday and Sunday, October 18-19, 2025 in Wellfleet, MA. This two-day family festival celebrates the town's famous oysters, clams and shellfishing traditions bringing together locals and visitors alike for a week...read more

A Different Drummer Craft Fair ~ October 4 & 5 ~ Brewster

Where: Drummer Boy Park, 773 Old Kings Highway, Route 6A, Brewster

When: -

How Much: Free

Categories: Festival

A Different Drummer Craft Fair at Drummer Boy Park Route 6A Brewster Hours 10 to 4. Featuring select craftspeople from Cape Cod and New England, over 40 booths will be at Drummer Boy Park Saturday and Sunday. You will find a wide variety of quality handcrafted items mad...read more

Mashpee Oktoberfest

Where: Mashpee Commons Green, Mashpee

When:

How Much: Free

Categories: Food/Wine

Mashpee's Annual Oktoberfest is organized and presented by the Town of Mashpee Special Events Committee. Oktoberfest is Saturday October 4th from 10AM – 4PM. Come celebrate the start of fall at this FREE family-friendly event! ????Join us for a full day of fun at Mashp...read more

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

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

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.

Oktoberfest in Chatham

Where: Kate Gould Park, 15 Chatham Bars Ave, Chatham

When:

How Much: Free

Categories: Festival

Listen to live entertainment, drink delicious local beer, browse numerous craft booths, and eat iconic Oktoberfest bratwursts.One of the main highlights of Oktoberfest in Chatham is Pumpkin People in the Park. The park is filled with creative and fun "pumpkin people" th...read more


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