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Each year at the second to last weekend in July the Edgartown Yacht Club hosts an annual regatta which includes the prestigious Round the Island Race. The 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.
Top racing teams have competed in this event.

Racing Teams that have stayed at the Captain Morse House.

2008 – Barking Mad – Jim Richardson – NYYC – 1st FARR 40 Class East Coast Championship

2013 – Barking Mad – Jim Richardson – NYYC – Farr 40

2014 – Interlodge – Austin & Gwen Fragomen – NYYC – 2012 First to Finish – 2014 3rd in TP52 Class

2017 – Spooky – Steve & Heidi Benjamin – Seawanhaka Corinthian & Noroton YC’s – First to Finish