Pumpkinfest in Damariscotta: When Pumpkins Take to the Water

A favorite autumn tradition from a corner of Maine we know well.

Autumn in Maine has plenty to recommend it: the changing leaves, the clear, cool air, and the small towns that seem particularly pleased to welcome the season. In Damariscotta, there is one more reason to visit. Every October, giant pumpkins take over the town.

We have a longstanding affection for this part of the coast. I have been coming to Maine since I was nine months old, and although our place is in tiny New Harbor, Damariscotta is the town we think of as our Maine hometown. For nearly anything beyond a loaf of bread or a gallon of milk, it’s where we go.

During Pumpkinfest, the familiar streets become a gallery of enormous painted and carved pumpkins. Artists turn these remarkable specimens into imaginative creations, displayed outside shops and along the sidewalks. We’ve had the pleasure of seeing the carvings many times, and photographs hardly convey their scale.

But the event that has made Damariscotta famous is the Pumpkinboat Regatta.

Yes, the boats really are pumpkins: giant ones, hollowed out and launched into the river, where costumed competitors paddle—or occasionally motor—their improbable craft while spectators crowd the waterfront. Some skim along surprisingly well. Others are rather less cooperative. Either way, the enthusiasm is contagious.

The story goes back to local growers Buzz Pinkham and Bill Clark, who helped turn a fascination with enormous pumpkins into a community tradition. Pinkham took an early pumpkinboat onto the water in 2005; the idea grew into the festival that Damariscotta celebrates today.

What we particularly love is the spirit of the occasion. There is real skill in growing the pumpkins and real artistry in decorating them, but nobody seems to have forgotten that the whole thing should be fun. It takes a town full of willing participants to make something this unusual work.

Here is a wonderful glimpse of the races, with the docks, the crowd, and the gloriously unlikely boats all in action.

Watch the Damariscotta pumpkinboat races on YouTube

It is one of the pleasures of returning to a familiar place: there is always something new to appreciate, and sometimes something delightfully peculiar. For anyone planning an autumn trip to Maine, Damariscotta deserves a place on the itinerary.

And if you happen to be there for Pumpkinfest, save a little time for the carvings. They’re worth the trip all by themselves.

Learn more about Damariscotta Pumpkinfest & Regatta.