First awarded in 1965, it commemorates the link between Block Island Race Week and Britain’s Cowes Week, after which Block Island Week is patterned. In 2005 the trophy was rededicated and will be awarded to the overall winner in the Round the Island Race.

1965 - Julie - Paul Campbell
1967 - Wild Goose - Bob Derecktor
1969 - Good News - Jakob Isbrandsten
1971 - Puff - A.M.B. Syndicate
1973 - Robin - F.E. Hood
1975 - Salty Goose - Robert E. Direcktor
1977 - Cascade - J.H. Milgram
1979 - Robin - F.E. Hood
1981 - Infinity - John B. Thomson, Jr.
1983 - Infinity - John B. Thomson, Jr.
1985 - Class 1 - Jubiliation - Jack S. James
1985 - Class 3 - Drumbeat - Blaire Brown
1985 - Class 4 - Full Tilt Boogie - Brenden Kelley
1985 - Class 5 - Devil's Fiddle - Lipkin/Fisk
1985 - 40 Class - Carronade - Robert James
1985 - Class 8 - Diogenes - M & K Clarke
1985 - Class 10 - UH-OH - Charles Smith
1987 - Class 2 - Gem - William Ziegler, III
1987 - Class 4 - Max Max - W. Musser
1987 - Class 10 - Free and Clear - John Schimenti
1989 - Class 1 - Carat - Wictor Forss
1989 - Class 2 - Blue Yankee - R.C. Towse
1989 - Class 3 - Menace
1997 - Kima - Nelson Weiderman
1999 - Jazz - John Fisher
2001 - Dynamo - Eriq Moog
2005 - Titan - Tom Hill
2007 - Blue Yankee - Bob & Farley Towse
2009 - Rosebud - Roger Sturgeon
2011 - Interlodge - Austen & Gwen Fragomen
2013 - Rival - David Curtis
2015 - Interlodge - Austen & Gwen Fragomen
2017 - Spookie - Steve & Heidi Benjamin
2019 - IRC - Beau Geste- Karl Kwok
2019 - All Other Classes - Bird - Ed Steedman
2021 - Emoticon - Jonathan Rechtschaffer
2023 - Cool Breeze - John Cooper