Although the small town of Damariscotta, Maine has a population of just over a thousand people, the annual Pumpkinfest draws in nearly 15,000 people from all over the U.S. The 16th Annual Pumpkinfest took place from October 11 to 13. In preparation, farmers around the state grow pumpkins as large as possible. The largest pumpkins from their farmers were submitted in the preliminary weigh-off competition, which took place on October 6. This year, the largest pumpkin set a state record, weighing in at 2,365.5 lbs. The world record pumpkin, grown in October 2023 in Minnesota, weighed 2,750 lbs, to put this year’s Maine winner into perspective. The growers of the three largest pumpkins were awarded $2,500, $1,300, and $750 respectively and were displayed for the rest of the week in a massive farm trailer in the downtown area. The smaller, un-awarded pumpkins adorn the sidewalks of downtown Damariscotta.

It is a yearly Pumpkinfest tradition for local volunteer artists to take on painting, carving, and decorating these pumpkins. However, there is a time crunch between the pumpkin “canvases” being distributed and the start of the festivities— just two days in total. It is truly impressive how quickly the artists complete their work in time for the festival go-ers. In years prior, pumpkin art has taken the form of lobsters, a pizza oven, The Beatles’ yellow submarine, Mike Wazowski, and many more creative, unconventional designs.
The most attended Pumpkinfest event is the regatta. Once pumpkins have been distributed for artists, the remaining pumpkins that are large enough for a human to fit in are hollowed out and transformed into boats. The regatta begins with a relay race with up to six teams captaining a pumpkin boat from the town dock to a buoy offshore. Once they make it to the buoy, they turn around and head back to the dock to bail all the water out of their pumpkin. Then their partner hops into the pumpkin boat for round two. It should be noted that the pumpkins are not tested for performance before the race, resulting in at least one team each year immediately flipping over into the river. It’s all in good fun, as each team dresses up in costume with a different theme, featuring Thing 1 and Thing 2, gnomes, Minions, kings and queens and many more zany combinations.
This year’s fleet included five teams, dressed as butterflies, bananas, pirates, strawberries, and a bridal party. There was also a race between four local police chiefs, but two flipped their pumpkins before the race began. Those crafty enough to combine a pumpkin and an outboard motor competed in the next race, which was a feat of engineering. Boaters follow the same format of the relay, but must complete five laps from dock to buoy to win the race. These pumpkins are heavily modified to make them more buoyant to accommodate the extra weight from the motor and increase stability.
In 2022, one of the pumpkin motorboats was built with a small wooden house on top, and miraculously didn’t flip over. Last year, a unique rowable pumpkin raft was captained by a woman from Anchorage, Alaska. Her boat was built from many small pumpkins attached together, and the first of its kind, so she did not compete in a race, but rather showcased her craftsmanship. The boat was originally intended to be rowable, but oars were swapped for a kayak paddle in the end. This year’s motored pumpkins featured a rubber ducky, a unicorn, and a gnome.
On October 10, 2005, a Damariscotta native was the first to captain a motored pumpkin boat on the Damariscotta River. His friend at the start of pumpkin growing season, read a how-to book about growing large pumpkins and inside was an image of a pumpkin with a motor attached. Thus, the first pumpkin regatta was formed. In 2005, it was just one person, but two boats were captained in 2006. By 2008, the two founders had convinced the town of Damariscotta to make it an official weekend-long event.
Damariscotta’s Pumpkinfest is an incredible combination of testing the laws of pumpkin physics, local artistry, and boosting Maine’s tourist industry outside of the usual summer months.