Boats lined up at the start. —Chace Lewis

The salty sailors of Holmes Hole have enjoyed an exciting season of racing thus far. Every Thursday evening at 5 pm and Sunday afternoon at 2 pm, week in and week out, sailboats of all different classes, with remarkably different hulls, sail areas, and intended purposes, set out into the Vineyard Sound to race one another. Here, a Sonar — a beginner-friendly 23-foot keelboat — can compete confidently against a boat like Zebra, an elegant W-Class twice her length that might finish the same race 30 minutes ahead.

That’s the beauty of Holmes Hole sailing. Through a unique rating system, each boat is assigned a handicap based on factors like her waterline, sail area, cruising speed, and performance week to week. The result is an eclectic fleet of boats, skippers, and crews, bound by the Corinthian spirit, that compete in animated, good-natured racing on relatively even footing each week. There are sailors not yet 20 years old, many of whom teach sailing at the Vineyard Haven Yacht Club in the summertime, lining their bows up against seasoned skippers with decades of experience sailing and racing their boats all over the world. After the racing on Thursdays, sailors gather over dinner to hear the highly anticipated results and to debrief the day’s events.

Sunday provided a proper test for the fleet. A strong breeze built out of the southwest up into the 20-knot range, with blustery gusts swirling down the harbor. Eleven boats lined up to race Course 7, which would send them zigzagging back and forth between East and West Chop, sailing out around RGN (a red-and-green navigation buoy, one of many that the organization utilizes as course marks, in an area of the sound known as Hedge Fence West), and finally beating their way back into the harbor to finish at Nun 6, a red buoy that marks the ferry channel in Vineyard Haven Harbor. With the breeze on and an ebbing tide, the fleet made quick work of the 10-mile route. Campana, a bright yellow Pogo 30 skippered by Eric Widra, was first across the line, nearly an hour before the last finisher. Once handicaps were assessed, the fleet finished within eight minutes of one another, and Bob Simons and his J9, Easy Rider, won the day.

Clinging to the top spot on the season’s current overall leaderboard is Maitland — a Herreshoff Buzzards Bay 25 raced by the Hammarlund family. Two races remain for Maitland to defend her position — two more opportunities for the rest of the fleet to make a run at the cup.

Sailors curious about getting out on the water and in on the action are encouraged to visit holmeshole.org to learn about getting involved. We warmly welcome any monohull sailboat over 15 feet in length, and our skippers are often looking to enlist the help of willing crew. This is a great community of passionate sailors, and we’re all fortunate to enjoy time on the water together in this special harbor.

Rawson Clough is fleet captain for Holmes Hole.

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