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The 238-mile race was started in 1932 and takes racers from Stamford east to Buzzards Bay and back. The first race had 23 starters with five finishers. The race has been held every year since its founding, except for three years during World War II.
It is also the final race of the Northern Ocean Racing Trophy series, the New England Lighthouse Series and the Doublehanded Ocean Racing Trophy.
In 1982 the race was described by Bob Bavier in Yachting as one of the "yachting classics." and:
- The greatest distance races of the world have several things in common -- a challenging course, competitive fleets and an interesting array of famous yachts. By those standards, the Stamford Yacht Club's Vineyard Race rates close to the top. Like a miniature Fastnet, the Vineyard has a combination of coastal cruising, where currents play a big role, a stretch of ocean sailing, and a mark to round -- the Buzzards Bay tower -- before returning.
The fastest time to complete the Vinyard course was set by Fujin in 2017. The Bieker 52 catamaran, skippered by Greg Slyngstad of Seattle Yacht Club, broke the old course record by five hours, finishing the course in 15 hours, six minutes and 50 seconds, 15:06:50 hours. The fastest time by a monohull was set by the US Merchant Marine Academy Foundation's Volvo 70, WARRIOR, the same year. Skippered by Stephen Murray, Jr., WARRIOR covered the course in 17 hours, 42 minutes and 9 seconds.
The race is several races in one. Competitors must navigate Long Island Sound before passing into Block Island Sound through one of several narrow passages where there are tough tidal currents. After rounding the tower they must leave Block Island to starboard before heading back into the Sound. A typical race involves a variety of conditions.
In 2019 Stamford Yacht Club held the 85th running of The Vineyard Race.