Paddlers make waves at annual Middleboro canoe race

May 5, 2025

MIDDLEBORO – Canoers managed to stay right-side up in their boats, but that doesn’t mean Middleboro’s annual canoe race on Saturday, May 3 was all smooth sailing.

Only eight boats participated in the race this year, likely since the event was postponed from its original date of April 26 due to rain, said Middleboro Parks Department Director Fran Cass. The canoe race was followed by the annual duck race, both of which are fundraisers for the Middleboro Parks Department.

Many canoers got stuck on rocks due to the river’s low water levels. But on the sidelines were eight-year-old Teigen and his aunt Wendy Freitas offering them words of encouragement. Freitas remembered how she used to bring her children to the event every year. “Now, I bring my nephew,” she said, adding “this is our Saturday adventure. We’re lucky Middleboro has so much to offer.”

The day may have yielded a low turnout among boaters, but those who showed up had a great time, for many reasons.

“I just enjoy being on the water. It’s my safe space,” said Middleboro resident Crystal Winslow, who traversed the river in a bright pink kayak. She kayaks the Nemasket all year round and loves the sense of peace she experiences when she’s surrounded by nature, she said.

The wildlife along the route was also a highlight for Middleboro School Committee member Allin Frawley.

“It’s amazing out there,” said Frawley, noting that he got to see osprey, blue heron and a lot of turtles, as he and his twelve-year-old son Sullivan paddled up the river. The Frawley family makes it a point to show up to the race every year.

The first time Sullivan, “Sully,” participated in Middleboro’s canoe and duck race, he was just four years old, according to his father. “I bought him his first kayak when he could spell his name,” he said.

The Frawleys’ were the first team to cross the finish line at Oliver Mill Park.

For Fran Cass, the best part of this event, which has been held in Middleboro since 1969, is hearing the stories that come out of it — of families, partners, and kids getting competitive with each other. “If you can do this race with someone, you know you can get along with them,” he noted with a chuckle.

The canoe race was followed by the duck race, in which numbered rubber ducks that registrants have bid on are dumped in the river; the first three ducks to cross the finish line earn a $100, $75, and $50 prize, respectively.