Things to Do on Cape Cod in September

Things to Do on Cape Cod in September

The best kept secret about Cape Cod? September is one of the top months to visit the Cape. The weather is still gorgeous, but the flocks of visitors and traffic have dissipated so you can explore all of the hidden gems in our area. There are tons of events going on all month long, so why not plan a getaway to Cape Cod this September?

Friday, September 6 – Sunday, September 8: Windmill Weekend (Eastham)

Windmill Weekend has something for everyone – live music, food vendors, a parade, car show, and road race. Check out the schedule and plan your stay so you can get to know one of our favorite towns on the Outer Cape!

Saturday, September 7: Cape Cod Comedy Fest (Falmouth)

Cape Cod Comedy Fest returns for its seventh year with talent like Jon Stetson, from The Mentalist. The performances take place both indoors and out, and food and beer trucks will be on-site, making it the perfect date night!

Saturday, September 14 – Sunday, September 15: Harwich Cranberry Arts & Music Festival (Harwich)

Browse the more than 150 vendors on site to try local foods and shop local crafts at the Harwich Cranberry Arts & Music Festival. Then, swing by the CranJam 2019 10th Anniversary Music Festival right next door to hit the dance floor or relax on the grass. 

Saturday, September 14: Cape Cod Roots and Blues Festival (Orleans)

Enjoy live music from G. Love & Special Sauce, Citizen Cope, Chadwick Stokes & The Pintos, Mihali, and Clearcola at Cape Cod Roots and Blues Festival by picturesque Nauset Beach in Orleans. The festival, which is in its second year, brings together locals and visitors alike for a day by the water with local food trucks, breweries, and wineries. And, a portion of the proceeds will be donated to Friends of Nauset Beach to protect the natural environment. 

Planning your Cape Cod vacation this September? We still have rooms available! Book yours today.


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This Valentine’s weekend 2020 I chose Brewster and the Cape to propose to my fiance! I could not have picked a better inn to stay at. In all ways the Inn by the Sea is warm, comforting, and fun for all ages. Amy helped plan my post proposal fun secretly with chocolate covered strawberries, flowers, champagne, and mimosas in the morning!! Thank you Amy and staff for an amazing, memorable trip!

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