This story has been updated to include the winners in each category, and other recognitions. 

ROCHESTER – Before the first crack of the starting gun at the Rochester Memorial Day Boat Race, two-and-a-half-year-old Leeland MacGregor wanted to join his dad, Ian MacGregor, in his boat.

“He wanted to come along for the ride,” said Ian MacGregor, who was one of 100 people who registered for the 90th annual race on Monday, May 27.

Forty-seven teams of two racing in homemade canoes and six single kayakers took on this year’s challenge.

For many Rochester residents, like David Souza, the 12-mile race down Mattapoisett River is “a thing you have to do if you live in Rochester.”

Souza, who said he has attended the boat race his whole life, watched boaters emerge from a culvert under Wolf Island Road – the halfway point of the race.

There, racers carry their boats over land for several yards while traversing a cranberry bog.

Also along that stretch was Rochester resident Sue Moore who waited for her grandson and son-in-law to pass by in Boat 18.

According to Moore, her grandson, Wyatt Harding, has diabetes, so she waited along the river with a Gatorade bottle in each hand, ready to toss them into the boat.

“Last year I climbed a tree to drop Gatorade into their canoe,” she said. “I knew they needed a drink, so I got over there and dropped it in.”

At the corner of Route 6 and River Road in Mattapoisett, a crowd gathered to watch boaters cross the finish line.

One spectator, Rochester resident and former boat race competitor David Watling, waited for his son, daughter-in-law and two grandchildren to finish the race.

“It’s great seeing three generations [compete],” said Watling. “It’s really fun to see a Rochester tradition [keep going strong].”

The first team to cross the finish line was Ian MacGregor and Eli MacGregor in Boat 1. They finished third in the open division with a time of 1:55:21.

Ian MacGregor said he has competed in the race for over 25 years.

“Practice definitely makes a difference,” he said. “This year we only got practice in once … the more you practice the better you get.”

Boat 6 – which pulled in right behind the MacGregor’s – was piloted by Paul Milde and Alex Milde. The pair came in first in the open division with a time of 1:50:47.

“It’s hard, it’s a lot of fun,” Alex Milde said.

After the race, Paul Milde said that he was going to take down his storm windows. Meanwhile, Alex Milde said he’ll be taking a nap.

Placing first in the Co-Ed division were Heather Veilleux, Rochester, and C.J. Hedges IV, Marion, with a time of 2:01:48.

In the Parent/Child Division Katelyn Watling, Rochester, and William D. Watling III, Rochester, finished first with 2:01:05

Anthony Coelho, Middleboro, finished first in the Kayak Division with a time of 2:27:22.

Ellsea Roy, Rochester, and Kristen Roy, Rochester, finished first in the Women’s Division with a time of 3:00:16.

And in the Junior Boys Division, Henri Roy, Rochester, and Mason Zell, Rochester, finished first with a time of 2:42:28.

Every year, the oldest person finishing the boat race receives the Old Man River Award, and this year it went to Roland Martin of South Carolina.

Finally, Peter MacGregor, Jeffrey Eldridge and William D. Watling III were honored for participating in the boat race for 50 consecutive years, 41 consecutive years, and 25 consecutive years, respectively.