the 32nd annual Great ’Round Gerrish Island Race and Cruise 

Almost 400 years ago, English settlers sailed into Portsmouth Harbor to set up camp at Strawbery Banke, the third English settlement in the New World. They disembarked from their great ships and rowed the final distance to shore in tiny rowboats, starting a tradition that would continue for centuries.

In 1972, Michael Gowell moved to the Seacoast and purchased a wooden dory instead of the septic system he needed for his new house. After discovering the circumnavigation route of Kittery’s Gerrish and Cutts islands, he decided in 1975 to share that experience in the form of an annual race. Wooden dories (rowed, poled or sailed) raced around the island. Modern rowing shells that could handle moderate seas were rare, and kayaks were still foreign to local waters. Thirty-two years later the race still exists, with a greater variety of boats but in the same spirit and with the same simple rules: row, paddle, push or sail your vessel around the island as you best see fit, and don’t throw rocks at competitors.

At 11 a.m. on Saturday, Oct. 7, hundreds of people flooded the road at the head of Chauncey Creek in Kittery Point, Maine. Spandex-outfitted athletes with carbon fiber paddles mingled with wool-clad rowers hefting wooden oars. Dogs sniffed each other from the ends of leashes. Parents held children and pointed out unique boat designs. Grandmothers paddled canoes along the calm, protected headwaters of the creek with their grandchildren. Kayaks now account for the majority of the participants, though they’re more tolerated than embraced by the traditional wooden boaters.

The bang of a miniature cannon marked the noon start. The streamlined rowing shells took off first, with wooden dories similarly equipped with sliding seats close on their heels. Lightweight carbon fiber and fiberglass kayaks came next as a wild, colorful, splashing flotilla. Strung out behind the more standard crafts came the one-of-a-kinds: the lumbering giants, the viking ships.

The course offers a greatest-hits version of paddling on the Seacoast. Distinct settings surrounding Gerrish Island range from calm creek to salt marsh to open ocean to tidal river. The first part of the race route snakes north through the Rachel Carson National Wildlife Refuge between the island and the mainland. At low tide, the salt marsh is unnavigable: steep muddy banks are exposed to daylight, and the deepest part of the creek beds are all but revealed. But at high tide, the swollen creek meanders its way across the wide expanse, and egrets and an occasional heron perch among the eelgrass and seaweed. At the height of an especially high tide, as during the race, the marsh creek is transformed into a wide, solid, shallow expanse of water, the boats and kayaks able to paddle in a straight line, only occasionally bumping into a patch of water too shallow to navigate.

The marsh soon opens up into the wider bay of Brave Boat Harbor and the changes character completely. The boats passed a column of pilings, remnants of an elevated train line that once crossed the water from York to the island. A northeasterly wind blew right into the mouth of the harbor, bringing a battering headwind and ocean swells into the inlet. The wind and waves kept the boats close to shore as they rounded the northern end of the island and entered the open sea, rocky beaches lining the numerous coves along the coast, the flux and movement of the waves hiding granite boulders just below the surface. After a long pull down the coast, the course hugs the sandy shore at Fort Foster, crosses under the pier between the forts and Wood Island, and enters the mouth of the Piscataqua River.

The finish line—uninhabited Fishing Island, just off Kittery Point Town Landing in Pepperell Cove—is about a mile away from the start as the gull flies, though the trip is about six miles by boat. For one afternoon each fall, the tiny island becomes the hottest spot on the Seacoast. The race’s $15 entrance fee includes steamers from Finestkind Fish and beer from Smuttynose Brewery, and the clams are steamed in a metal garbage can right on the beach.

The Gerrish Island race is more about camaraderie than racing, though there are a handful of competitors vying for the winning times in each of the categories.

The competitive spirit dies away as the bulk of the participants trickle onto the rocky island by 1 p.m., and the finish line becomes a party. Like a triumphant viking raiding party, the victors—meaning all who made it to the finish line—feast and linger for hours on a sunny Saturday afternoon, before getting back into their boats to head back to the mainland and the 21st century.