Maynard MA man will cover 86 miles in 48 hours by canoe. Why he’s doing it

June 10, 2025

by Ruth Thompson | June 10, 2025 | MetroWest Daily News

Every year, Chester “Ozzy” Osborne takes on a paddle or bike trip that really tests his endurance. Two years ago, for example, he took two days to retrace the path, by canoe, of a raindrop from his yard in Maynard through several bodies of water until he got to the ocean.

This year, Osborne plans to paddle the entire 86 miles of navigable waters in the Sudbury, Assabet and Concord rivers in 48 hours. It’s a challenge he took on through OARS 3 Rivers, a nonprofit that focuses on protecting, improving and preserving the three rivers and their watershed.

“People have this great recreation area (right) in their backyard,” Osborne said. “My goal is to draw attention to it, get more people activated to go out and to be stewards.”

Maynard resident Chester “Ozzy” Osborne will attempt to paddle 86 miles through the Sudbury, Assaber, and Concord river in 48 hours to benefit OARS 3 Rivers, a nonprofit that protects, improves, and preserves the three rivers and their watershed. Photo Credit Chester Osborne

Trek begins with 3 a.m. launch from Marlborough

Osborne canoed frequently as a child, both with his family and through his association with the Boy Scouts. As he grew older, he didn’t get out on the water as often until he met a mentor on the job who reengaged his interest.

“My mentor was really into canoeing and wilderness hiking, and that motivated me,” said Osborne, who is currently chief operating officer at the Massachusetts Executive Office of Energy and Environmental Affairs.

He will launch about 3 a.m. on Saturday, June 21, from Hillside School Wildlife Sanctuary and River Access in Marlborough. He will travel along the Assabet River, but avoid the white water by carrying his canoe on land for about two miles in Maynard. Then he’ll drop back into the water and paddle to Talbot Hills Dam in Billerica.

“That’s a 30-plus mile paddle,” he said. “That’s a really big day.”

He’ll turn around and head up the Concord River to Scout Island in Fairhaven Bay in Lincoln, where he’ll spend the night. On day 2, Osborne will head out about 6 a.m. to paddle onto the Sudbury River to the Carol Getchell Reservation in Framingham. The last leg of the trip has him going back to the Concord River and to Route 225. The event ends at the Bedford boat ramp.

Chester “Ozzy” Osborne, a former Green Beret, enjoys the physical aspect of canoeing, as well as being able to enjoy the surrounding nature and scenic beauty. Photo Credit Chester Osborne

A good friend will run a support camp on the island with water and hot food.

“I will be very responsible for myself,” Osborne said. “If I need to pull over and take a nap, that’s what I’ll do.”

For his 48-hour trek, Osborne will have company at various sports along the way.

OARS executive director calls trip a ‘great undertaking’

Matt Brown, executive director of OARS, will join Osborne for about 22 miles. “We have pacers along several sections who will paddle with him,” Brown said.

He said Osborne’s 86 miles in two days is a “great undertaking.”

“I think it’s a great idea,” he said. “I hope he can do it. It’s a cool thing.”

He explained that Osborne’s route will spotlight the beauty and accessibility of the rivers, and the urgent need to remove barriers, like aging dams, to restore ecological health and resilience.

“Our rivers have historically not been given the best care,” Brown said. “We’ve done a lot of work to clean them up. They are important habitats for our local fish and other creatures, and a number of communities either directly or indirectly get their drinking water from these rivers.”

Osborne describes the skill—and comfort—of canoeing

Osborne said he enjoys “these micro-adventures” he undertakes.

“I used to be a big-time adventurer, but now I’m a husband and a father and I just don’t have the time,” he said.

Physical activity is nothing new for Osborne, 47. He served 21 years in the military, most of them as a Green Beret. But he acknowledges the challenge that paddling that distance in such a short period of time can be.

“Canoeing is so easy to do that people don’t realize how much skill can go into it,” Osborne said. “With this, I wanted to get a little out of my comfort zone.”

To prepare for the trip, Osborne has been getting up at 3AM on Saturdays and heading to the river.

He enjoys canoeing because it “allows you to travel incredible distances and see so much of nature—the sky, the land, the water.”

“I get to see muskrats, beavers, water snakes and all types of birds,” Osborne said. “My brain never stops, but when I’m canoeing it’s the only time my mind is quiet. There is something about paddling down a river that has you present in the moment in a way nothing else does.”

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River Log

~30%

of the SuAsCo rivers watershed is wetlands, crucial for wildlife habitat and water quality

~30%

of water samples in the SuAsCo rivers watershed contain PFAS, leading to increased monitoring and remediation by local authorities and environmental groups

~70%

of dams in the SuAsCo watershed are over a century old, requiring extensive upkeep and presenting obstacles to river restoration and fish passage

>40%

of the land within the watershed is publicly accessible, offering recreational opportunities such as hiking, boating, and birdwatching to the community

~15%

of the land in the SuAsCo rivers watershed is covered by impervious surfaces such as roads, rooftops, and parking lots. This contributes to stormwater runoff and water pollution issues

>40%

of the land within the Sudbury, Assabet, and Concord rivers watershed is publicly accessible, providing endless opportunities for paddling, hiking, and wildlife exploration.