2025 Damariscotta Pumpkinfest & Regatta

It’s no secret that fall is the time to celebrate all things pumpkin, but Damariscotta’s Pumpkinfest and Pumpkin Regatta have truly mastered the art.

This annual celebration promotes local talent, businesses and produce with a highly memorable series of pumpkin-themed events. As an added bonus, the festival is 100% volunteer-run and always free to the public.

One of the biggest events is the Pumpkin Regatta, where brave souls take to the Damariscotta River in hollowed out gargantuan gourds, like a real-life Thumbelina.

 This year the regatta was on Sunday, Oct. 12. The hollowed-out makeshift boats were “built” on Saturday, created from Atlantic Giant Pumpkins, planted by local schoolchildren and grown by local volunteers. 

The pumpkins were decorated with care, and christened with fun names like “Red Baron” and “The Gnome Boat.”

The contestants arrived on Sunday decked out in elaborate costumes, many with wetsuits underneath to guard against the cold waters. Costumes ranged from crazy colorful cowboys with giant hats, to cartoon characters, witches and everything in between.

The events kicked off with the Star-Spangled Banner, sung by Lincoln Academy students, followed by the blessing of the fleet in the form of a fun poem.

Next were five heats of races, where participants raced from the docks to a buoy and back – if their good ships made it, that is. Some took on water or flipped over almost immediately, amid cheers, applause and laughter. 

While some contestants took an early lead, unexpected collisions some sinking vessels meant the winners of each heat was anyone’s guess.

Winners included Todd Sandstrom, piloting the pumpkin “Naked and Afraid” – named for a lack of decorations, and Robert Watts paddling the Red Baron.

Following the heats were two rounds of a relay race, where paddlers took their boats to the buoy and back, then disembarked and changed pilots for a second race around the buoy and back.

In the first relay, Briar Bouthot and Sean MacCarthy, in bright orange suits and matching giant cowboy hats, came out as the winners. In the second relay, the winners were Alice Andrenyak and Jessica Goodwin, decked out as Witches and paddling a giant pumpkin decorated as a black cauldron.

Of course, the process of exiting the vessel and a new paddler getting in was the hard part, where good leads turned into a second-place finish.

Finally, the regatta ended with the motorboat races, also known as the “power pumpkin” division. These good ships were also carved from hollowed pumpkins. The race involved a loop around the bouy, followed by a slalom, capturing a flag, and returning to the dock.

Buzz Pinkham, piloting a ship dubbed the Pink Pony and painted like the same, won the motorboat event against Josh Felter in the Rubber Duck and Tom Lishness in his Gnome Boat. 

In the end, though, everyone was a winner – both in the crowd and participating – with this fun and festive October event.