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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Amy and her staff are incredible. The attention to detail is hands down the best. Given all that is going on in this Covid-19 world, we felt safe and comfortable. Check-in was contactless. Our room was perfect. The breakfasts were wonderful and loved the cookies in the afternoon. The icing on the cake was Sweet Pea, Amy's dog, an absolute love! Amy, thank you, we'll be back!

— TripleAMom, July, 2020


Outstanding getaway!

This was our second time staying at this lovely inn. The rooms are tastefully decorated and the grounds are both spacious and tranquil. There is even a pool which is an excellent way to cool off after a day exploring the nearby trails or bike path. The breakfasts are creative and delicious and very filling. Amy, the owner and innkeeper is wonderful. She takes great care of the property and is so welcoming to her guests. She is very gracious in helping with advice on what to do in the area and making dinner reservations. We were among her first guests as Massachusetts began to "open up" during the Covid 19 crisis. She took great care to assure that everything was done to make her guests safe and comfortable. We look forward to returning.

— Pat I., June, 2020


A very enjoyable and relaxing stay

We had another wonderful experience here at Brewster By The Sea.  Lovely walks on the Flats and enjoying the local food!  In spite of COVID, Amy & staff helped us feel SAFE and at home!

— Ross & Patricia, Delmar, NY    6/26/20


Another Memorable Weekend

Thank you for everything, Amy!  We had a wonderful getaway.  Your Inn and all of your extra touches make this place so special.  We look forward to returning soon. 

— Patti & Joe, North Readin, MA     06/14/20