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Best Fall Festival in Maine – Damariscotta Pumpkinfest and Regatta

Giant pumpkin earns award for size


You may be wondering what on earth pumpkins have to do with regattas. Plenty, here in Damariscotta, Maine. The 13th Annual Damariscotta Pumpkinfest & Regatta, voted “Best Fall Festival in Maine” by Travel and Leisure magazine in 2017, is a widely popular event designed to educate the community on the best way to grow Atlantic Giant Pumpkins. This annual event is so popular, that it has been featured in multiple TV shows, such as ABC’s “The Chew” in 2012, CBS News “Sunday Morning” show in 2013, as well as The Travel Channel, The Discovery Channel, German Public Radio, and BBC’s “Global Guide,” among others. Held for ten days in early October through Columbus Day weekend, this fun family festival provides more than horticultural education. The 10-15,000 visitors enjoy a variety of activities, like pie-eating contests, pumpkin carving, a parade, and the Pumpkinboat Regatta, while raising funds for the coastal community.

Pumpkinboat Regatta

One of the highlights of this popular annual festival is the Pumpkinboat Regatta. Would you believe that participants paddle and race their 400-700 pound, hollowed-out pumpkins down the Damariscotta Harbor? This race is definitely one not to be missed, and will also be live-fed into the local theater for those who would like to watch it from there.

Pumpkinfest Events

Here are just some of the fantastic festival events.

View the full Pumpkinfest Events schedule


Located only a half-mile from downtown Damariscotta, the Newcastle Inn is the perfect place to stay during the Pumpkinfest. Our elegant and comfortable accommodations offer beautiful views of the Damariscotta River, a delicious homemade breakfast each morning, and plenty of amenities to enhance your stay. Book your room today or contact us for more information.

Small table and chairs set for two on deck overlooking the water.

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