This story was originally published in October 2023. The 2025 Damariscotta Pumpkinfest and Regatta is being held Oct. 10-13.
DAMARISCOTTA, Maine — In 2005, Buzz Pinkham was the first person to captain a pumpkin in the harbor in Damariscotta. Two decades later, people come from all over the country to race pumpkin boats in Damariscotta’s Pumpkinfest Regatta.
The Damariscotta Pumpkinfest happens annually on Indigenous Peoples’ Day weekend to honor the first day Pinkham took his pumpkin boat into the harbor. The festival includes a contest for the largest pumpkin, Maine artists decorating and displaying giant pumpkins, a parade, a derby and of course, the regatta. The festival has been going on for 15 years after Pinkham and his friend, Billy Clark, convinced the town to make the Pumpkinfest official.
Pinkham, a Damariscotta native, wanted to grow giant pumpkins. He and Clark picked up “How-To-Grow World Class Giant Pumpkins III” by Don Langevin, and in the book was a picture of someone with a giant pumpkin attached to a motor. Pinkham decided that day that he was going to make a boat out of a pumpkin.
Clark said he would make the boat, but he wouldn’t get in it. Pinkham happily volunteered to pilot the boat.
“I says, ‘Alright, I’ll get in it, I’ll get in it,’” Pinkham said. “So that whole first growing season, that whole summer, I was like a kid waiting for Christmas.”
One of the paddlers sits on an overturned pumpkin boat to spectate the race at the Damariscotta Pumpkinfest Regatta on Oct. 9, 2023.
A pumpkin captain dressed as a viking races other motorized pumpkin boats at the Damariscotta Pumpkinfest Regatta on Oct. 9, 2023.
Two paddlers battle for second place at the Damariscotta Pumpkinfest Regatta on Oct. 9, 2023. The regatta is a tradition in the coastal Maine town where people come from all over the country to race boats made out of giant pumpkins. The pumpkins are weighed and painted, and the racing teams often dress up to race their pumpkin boats in the harbor.
The Pumpkin Queen leads the paddlers to their pumpkin boats at the Damariscotta Pumpkinfest Regatta on Oct. 9, 2023.
So, on what was then Columbus Day 2005, Pinkham and Clark took the pumpkin boat they made for a spin in the harbor. The following year, there were two boats in the water. By 2008, Clark and Pinkham convinced the town of Damariscotta to make the Pumpkinfest official. By bringing in vendors and cash prizes for the largest pumpkin, people flocked to Damariscotta for the festival.
This year, the festival had over 300 volunteers, and they’ve been planning it since March, said Clark, who is director of the festival. Clark said the purpose is to bring money into Damariscotta businesses before the winter.
“Everybody is a volunteer,” Clark said. “The reason we do it is to try and help some of these businesses get over the hump and make it through the winter. Because it’s a long, cold, dry winter around here and some of these little businesses need all the help they can get.”
