The Vineyard Race was established in 1932 and is one of the premier distance races on Long Island Sound. The Race now has three courses – Vineyard (238 nautical miles), Seaflower Reef (143 nautical miles) and Cornfield Point (116 nautical miles). All courses start and finish off Stamford, Connecticut. The traditional Vineyard Course starts from Shippan Point around the Buzzard Bay Light Tower then leave Block Island to starboard on the return trip back to Stamford. Currents play a role in exiting and entering Long Island Sound as well as in Block Island Sound. The Race is held Labor Day weekend with the start of the race beginning Friday afternoon. The Race always attracts a competitive fleet and experienced sailors.
Bob Bavier of Yachting magazine described the race as a miniature Fastnet Race, as the Vineyard has a combination of a coastal cruising, where currents pay a big role, a stretch of ocean sailing and a mark to round – the Buzzard Bay Tower – before returning.