Anything Goes at the Archipelago Rally

For southern New England sailors who just love getting out on the water, the anything goes Archipelago Rally is a must-do event.

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Boats and sailors of all stripes participate in the Archipelago Rally, held each fall in New England. To enter, the boat needs to be powered by wind.Peter McGowan

15-foot wooden tender, in three separate pieces, sitting on a seaweed-covered launch ramp. That’s how George and Lindsey Hill started their morning one day last October, preparing for their favorite regatta of the year. The couple bolted their home-built nesting dinghy together as kids skipped rocks across Massachusetts’ Westport River. Forty-eight other craft, all equally as unique as the Hills’ classy, varnished pulling boat with its lug rig, began to appear on the sandy riverbank. This was the Hills’ seventh time at the Archipelago Rally, held annually across Rhode Island and last fall in Massachusetts. For those in southern New England who love just messing about in boats, this late-season event induces giddiness.

“I never had a lesson. I just played around in boats,” says George, who spends the summers racing the famed 12-Meter Weatherly for his company, America’s Cup Charters in Newport, Rhode Island. “This is like so much of my youth. Rowing into breaking waves, swamping the thing, doing stupid stuff and learning from it on the water.”

Like many of the sailors who have been attending the rally over its 10-year history, George looks forward to this thrown-together event each fall so he can have his own relaxed racing experience. Started in 2006 by seven ex-college sailors looking to extend their season, the rally has taken on a life of its own, with well over 100 sailors on the water each year.

The concept is simple: Bring anything with a sail, and a “Portsmouth Yardstick” rating is given along with a start time for the pursuit-style race. The slowest boats start first, from the beach, in hopes of everyone finishing around the same time. A BBQ awaits finishers, and awards include a coveted last-place trophy and the Pine Needle Award, given to the craft with the most amount of yard debris remaining on the boat from storage.

In 2015, the quaint Spindle Rock Club hosted the rally. Many boats in the contest are summer tenders; this year, craft ranged from a diminutive Cape Cod Frosty to a Polynesian sailing canoe. A family of four aboard their Hobie 16 won after many years of trying. With children accounting for more than half the ralliers, it was no surprise to see kids passing their parents in the cool, swirling river waters.

“We’re trying to provide a fun on-the-water experience,” says Tracy Hayley Smith, who crammed into a Beetle Cat with five kids and an old friend. “Towing the Opti, flipping it, having raft-ups with friends in the summer, that’s the base line, and the rally is just an extension of that.” Hayley Smith and her crew never finished, but the children licked happily through a bag of Tootsie Pops. Like George Hill, she is a competitive sailor. But the rally is the only regatta where that tendency gets shut off. “The ratings are impossible,” she says. “Just roll with it. Sail as far as you can and enjoy it.”