Little can prepare you for paddling a boat made out of a 600-pound pumpkin. 

“I was told to ignore my kayaking experience,” said Michael Ball, 30, of Avon, Colo. 

For his first time competing in the Damariscotta pumpkin regatta, Ball paddled his pumpkin decked out as the “Red Baron” plane from the “Peanuts” comics while dressed as the character Linus. His aunt, Jaja Martin of Bremen, wore a Snoopy costume and has participated in the regatta for over 15 years. 

For professional sea kayak guide Alice Bean Andrenyak, 72, the difficulty of steering a pumpkin boat was part of the fun. 

“I kayak all summer. At the end of the season, I want more of a challenge,” said Bean Andrenyak of Brunswick. 

Bean Andrenyak has paddled in the regatta for 10 years. She has dressed as a lobster, butterfly and disco queen with hollowed-out gourds decorated to match. This year, she competed as a witch with a curly green wig and pumpkin boat painted black like a cauldron.

Bean Andrenyak said the event isn’t just fun for the racers, but the spectators as well. Several hundred people crowded the launch area to get a view of the race, many donning pumpkin hats to match the weekend’s festivities. 

“Sure we like our trophies when we win,” said Bean Andrenyak. “But the more we capsize, the more fun they have.” 

Over the holiday weekend, the annual Damariscotta Pumpkinfest and Regatta includes a pumpkin pancake breakfast, a pumpkin parade, a soapbox-style pumpkin derby where kids race pumpkins with wheels and a pie-eating contest. 

The most notable event is the pumpkin boat regatta, in which contestants race carved-out pumpkins weighing between 500 and 800 pounds around buoys on the Damariscotta River. Steering their organic crafts and racing in heats of either motorized or paddle-powered, contestants go out and back from a dock, knocking each other like bumper cars to the cheers of the crowd. 

Some pumpkin boats were painted as silver pots of soup complete with vegetables, the green horse of “Pumpkinhead Pete” and a pink pony, with contestants costumed as chefs, Shrek, a banana and a loon. 

Not all pumpkin boats needed a competitor’s shove to be out of the running, with some riders flipping out almost immediately after launching. Rescue divers were at the ready to help them back to the dock. 

Hannah Aisling, 30, came to watch the pumpkin regatta for the first time this year after growing up in Maine. 

“I put this event on my vision board for this year,” said Aisling, of Biddeford. “It’s so fun and quirky, I felt I really wanted to make it this year.” 

“And all the locals have been so nice, I really want to make it back next year too,” she said. 

Over the years, one pumpkin regatta contestant in particular has made his mark with a red pointed hat. Tom Lishness competes in the motorized pumpkin boat race year after year dressed as a gnome. 

Lishness, 67, was in the first pumpkin boat to float down the Damariscotta River in 2005, after some friends grew a 700-pound pumpkin and were inspired to make a craft from it. The lone pumpkin and its captain on the water drew spectators, and the next year there were two pumpkin boats on the river. 

“It really gave them something to look at when they drove over the river,” said Lishness, who lives in Windsor. 

In the following years, the complete Damariscotta Pumpkinfest and Regatta emerged from the excitement around this event. 

As for his iconic costume, Lishness said the theme was borne of competitive pumpkin growing. While photographing his own large pumpkins in the 2000s – including a 1,014-pound monster that broke the state record – Lishness set up garden gnomes to show the size comparison. Paying homage to the gnomes, he would stand them on the edge of his pumpkin boats as he raced them. 

Over the years, the statues on his pumpkin boats were recognizable. 

“The MCs would call it the ‘gnome boat,’” said Lishness. “They eventually said ‘Tom, you need to dress up as a gnome too.’” 

After some resistance, Lishness donned the gnome costume in 2018 and has taken it out every year since. With his white beard, gardening clothes and short stature, he already had many elements of the whimsical getup. His gnome hat? He ordered it from Etsy. 

“They convinced the gnome to finally put on a hat,” said Lishness.