A kaleidoscope of kayaks and paddleboards, along with one row boat, one Hawaiian outrigger, and one brave soul in a wetsuit all gathered at the mouth of Sengekontacket Pond in Oak Bluffs on Sunday morning.
Their goal?
Make it around the pond, under the Big Bridge, and through the yellow flag and stanchion on the ocean side of State Road before the last sausage made it off Mike Dowd’s grill. This was the 28th annual Oar and Paddle Regatta, and like the 27 that came before it, finishing the race was far more important than racing to the finish.
Unless your name was Dana Gaines.
“He’s only won 28 years in a row!” said event organizer and owner of Island Spirit Kayaks, Chick Stapleton.
Mr. Gaines finished the 2.4 mile course in just under 22 minutes, giving him enough time to dry off, claim his medal and, most importantly, his hot dog, before second-place finisher Brian Beasley made it ashore three minutes later.
All proceeds from the race went to Friends of Sengekontacket, an organization dedicated to the preservation of the beach and pond.
“It’s a beautiful day, the event sold out, and we had highest registration we’ve ever had online,” said Chris Hall, a volunteer from the organization. “The money goes to maintaining the banner beach, cleaning up litter, dredging, pretty much anything that will help this pristine piece of land.”
Ms. Stapleton’s company sponsored the regatta and provided their entire fleet of kayaks and paddleboards, ensuring everyone who paid the entrance fee had a ride. Of course, some, like Mr. Gaines and Mr. Beasley, came with boats of their own. Paddling a Stellar Fiberglass surfski and a hand-carved Randy Durbin cedar strip kayak respectively, the pair finished the race in first and second for the second year in a row.
“I like to say it’s all about the boat,” Mr. Gaines humbly attested afterward.
Some racers without kayaks modified boats from the Island Spirit fleet. Regatta veterans Bridgette Dunnigan and Roger Williams fashioned a plastic crate to the front of their kayak to hold Doki, their rescue dog. The makeshift captain’s box worked, as Doki’s Drift sailed ashore with a first-place canine finish.
Other racers, leaving the boats as-is, decided to modify their outfits instead. The Cramer family came over the finish line with bright-red lobster hats affixed to their heads.
“We had our dog last time, which made us the only boat in the ‘family with a dog category,’” Matt Cramer said. This year, the Cramers were the only boat in the ‘family in lobster hats’ category.
“We’ll do anything to support the health of Sengekontacket. It’s our playground,” Mr. Cramer said.
Suffice to say, the Cramer’s too came away with a first-place medal. Then again, medals in general weren’t hard to come by on Sunday.
“We’ve got medals for days!” Ms. Stapleton said. “Let’s go around and make sure everyone gets one.”
Island Spirit Kayak’s very own Megan Sonia was the first-place finisher for the women’s kayak category, winning with a handmade wooden boat her grandfather shipped from Canada. He even painted the 17 year old’s name on the bow.
Patricia Clark, who flew in from Long Island for the race, claimed second.
Collin Stapleton, at age seven, was the youngest solo-kayaker to ever finish the race. Was he scared to be in the boat alone?
“No, because I thought it would be a shorter race than it was,” Collin said. “But I’m happy I finished. And I stabbed two jellyfish!”
On the other end of the age spectrum, 90-year-old Herb Foster and his co-paddler Patricia Tyra received the senior paddlers award. Mr. Foster dedicated his medal to fellow veteran and Senator John McCain, who had died a day earlier.
Most of the stand-up paddleboarders went home with hardware. Anna Morin nabbed the first-place prize, besting friend Paul Hyzak by only 16 seconds. There was even a stand-up paddleboard family category, with father-son duo Tim and eight year old Beckett Sheran taking first.
“I just help the balance” Beckett admitted. After trying his hardest to stay dry for the hour-long journey, Beckett had different plans for the rest of the hot day.
“Now let’s go get a dip in the water,” he said.
As Beckett ran into the State Beach tide, a man in a wetsuit emerged onto the sand. At an hour and 12 minutes, swimmer Matt Coffey proved that it was the Oar and Paddle Regatta in name only, finishing the course with neither. Mr. Coffey’s daughter Ada and son Rye ran up to hug their dad before he could get out of the water, his hands free to hold them.
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