Edgartown Yacht Club held its first race around Martha's Vineyard Island in the summer of 1938, and except for the years of the Second World War the race has been an annual event since then. For a number of years the course was extended to round the Buzzards Bay Tower, but today the traditional tight course around Martha's Vineyard Island is used.
Normally it is possible for both cruising and racing boats to finish the 52¼ nautical mile course by late afternoon or early evening. If the tidal currents or wind conditions make going slow, the Race Committee will finish the race just north of Menemsha.
The course itself is a splendid sail. It is reminiscent of the race around the Isle of Wight in England, which was the course of the first America's Cup. The distance around Martha's Vineyard is similar (only a few miles longer); both courses have views of cliffs, headlands, villages and open water; and the tidal currents and wind effects are important in both. The course around the Vineyard passes in sight of the seven lighthouses of Cape Poge, Gay Head, Tarpaulin Cove, Nobska, West Chop, East Chop and Edgartown. In the morning the fleet sails between Martha's Vineyard and Nantucket along the east beach of Chappaquiddick. At midday they are in the open Atlantic Ocean with views of the south coast of the Vineyard. In the afternoon, rounding the gorgeous cliffs of Gay Head, the fleet sails up Vineyard Sound which was the second busiest body of water in the world during the age of sail.
The 'Round the Island race has always been a part of the sailing calendar for both the great names of yacht racing and also the cruising sailor.
In addition to class prizes, there are a number of distinguished awards based on perpetual trophies.
- The VENONA Trophy is presented to the yacht in the spinnaker divisions with the best overall corrected time. The trophy was given in 1938 by Commodore E. Jared Bliss and named after his ocean racing yacht which won the Bermuda Race in 1908.
- The UPBEAT Cup is for the best overall finish in the non-spinnaker division. In recent years about half of the entries in the 'Round the Island Race have been in this division. In 2011 Commodore Owen C. Smith gave this cup, named after his yacht which had done this race more often than any other boat -- always in the non-spinnaker division.
- The CONCORD Cup is awarded to the first yacht to finish -- the Line Honors winner. The Cup was given in 2000 by Commodore Robert F. Hoerle and named after Gosnold's ship which, in 1602, was the first recorded sailboat to get around Martha's Vineyard.
- The OCEAN RACE Trophy goes to the best finish in each division by a yacht entered by an Edgartown Yacht Club member. It was given by Commodore Hugh Bullock in 1959.
- The COOK Award is for the best finish among Service Academy yachts. It was named in memory of Hobart A.H. Cook, by his wife, Molly, who was for many years the Secretary of the Club.
- In addition, there is the TEAM Trophy which is awarded to the 3-yacht team made up of entries from a given club representing both divisions with the best combined corrected time.