Stamford Yacht Club is the proud sponsor and host of the Vineyard Race. This classic yachting event began in 1932, and typically attracts over 100 boats of all sizes from all over New England. The 238-mile course stretches from Shippan Point in Stamford, Connecticut to the light tower at the entrance to Buzzard's Bay, and then returns to the finish in Stamford Harbor, leaving Block Island to starboard on the way out and back.  There are two shorter courses that run 116 nm and 143 nm for those who would like to be part of the event without going the entire distance. Those who are successful often credit local knowledge of these tricky waters, along with a good deal of luck. 
 
The Vineyard Race was described in Yachting Magazine as follows: "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."
 
There are many who feel that no sailing resume is complete without the Vineyard Race. The saltiest sailors, who have completed ten or more Vineyard Races, have earned entrance into The Buzzard Society.

The race begins on the Friday before Labor Day each year, followed by the always-epic awards party which is held on the SYC lawn that Sunday.