9 Fall Fest’s We Love on Cape Cod!

Excellent Blob by Kristin Amico

Local artists, succulent oysters and homegrown brews set the stage for some of autumn’s most celebrated festivals on Cape Cod. Fall is also one of the best times of year to visit – with its crisp air, crimson cranberry bogs and winding nature trails –  so mark your calendar now for these best bets.

Local artists, succulent oysters and homegrown brews set the stage for some of autumn’s most celebrated festivals on Cape Cod. Fall is also one of the best times of year to visit – with its crisp air, crimson cranberry bogs and winding nature trails –  so mark your calendar now for these best bets.

One of the Cape’s most beloved celebrations is Eastham Windmill Weekend (September 6-8) – the historic Eastham Windmill is the oldest of its kind on Cape Cod, and the festival dates to 1977. Nosh on local food on the Windmill Green, while watching a parade, perusing a craft fair and checking out the antique car show. There’s also a dunk tank (a great relief from the high temps) and daily entertainment from local bands, ranging from blues to jazz.

The reason folks love the annual Fall for Harwich festivities is because it spans a glorious two months, so you don’t have to cram all the fun into just a day or two. Throughout September and October, there are historic walking tours of the town, evening lantern tours, a parade, farmers’ markets, and plenty of other outdoor fun. One of the most popular events is the Harwich Cranberry Arts & Music Festival (September 14-15), featuring craft vendors, food trucks and evening fireworks.

A toast to the area’s booming craft beer movement, Cape Cod Brew Fest is on tap for its 7th year (September 21) under the tent at the Cape Cod Fairgrounds in Falmouth. Sample pours from more than 100 breweries featuring 300 styles of beer, from sours and seasonals to lagers and ales. Tickets (for those 21+) include all beverage samples and live music. Food vendors are also on hand to keep you well fed!

Does sipping wine while reveling in Americana bluegrass and folk music sound like a good time? Then the Vinegrass Music Festival (September 29) is the thing for you. The boot-stomping fun at Truro Vineyards is a fitting farewell to summer on Cape Cod. It’s a full day of live music from such bands as Smooth Hound Smith,The Mammals, Monica Rizzio & The Even Keel and headliner Parsonsfield. Sample local wine or cocktails from Twenty Boat Rum and Dry Line Gin, and enjoy savory snacks from the Blackfish food truck. Attendees are encouraged to bring beach chairs and blankets.

For more than 30 years, the Mashpee Oktoberfest (October 5) has ushered in the festive autumn season on the Village Green at Mashpee Commons. Celebrate with a traditional beer garden, German food, authentic German music, and local craft vendors. And there’s plenty of fun to keep the kids busy and smiling, too. They can decorate pumpkins and gourds, dance to family-friendly bands or catch a kiddie train ride around the Commons.

Farther down Cape, another Oktoberfest celebration will draw people to Chatham (October 26) for old-fashioned games, tasty German fare and beer, live music at Kate Gould Park, where the much anticipated Pumpkin People in the Park will also be on full display!

Columbus Day Weekend buzzes with activities at the Yarmouth Seaside Fest (October 12-14). Now in its 41st year, the annual celebration brings together tourists and locals alike for everything from food contests and 5k races to an art sale featuring 125+ artists and crafters from across the country. Live music, a kayak and canoe race, pie‐eating contests, sand sculptures, a festive parade and harborside fireworks round out the fun.

We might be biased, but we think Wellfleet oysters are the best in New England with their bright, briny flavors! Every year, these famous bivalves are celebrated at the Wellfleet OysterFest (October 19-20). Devour oysters, clam chowder, stuffed clams, and other traditional New England fare. In addition to food, there are cooking demos, live music, family activities, an arts & crafts sale, and craft beer and wine vendors. Don’t forget to belly up to the raw bar for the annual shuck-off, where local amateurs compete for the coveted prize.

Provincetown is always throwing a party, and Halloween is one of the biggest. The annual Halloween in Provincetown (October 31-November 3) celebration includes adult dance parties, spooky evening tours, the well-attended Saints and Sinners Costume Ball, and the Day of the Dead Performing Arts Festival, which culminates with a procession down Commercial St through town. There are family-friendly events too, including a kids’ parade and trick or treating for the little ones.

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