Presented in memory of Past Commodore Hugh Kilmer. To the best Yacht at Block Island Race week 25 years old or older, substantially unaltered, with the best point score for the week.

1971 - Callooh - Jack M. Brown
1973 - Rhubarb - Benjamin B. duPont
1975 - Dolphin - Bruce & John Lockwood
1977 - Dolphin - Bruce & John Lockwood
1979 - Swift - US Naval Academy
1981 - Storm - Bruce Barnard
1983 - Pampero - R.S. Andrews, Jr.
1985 - Rabbit - Daniel P. Dyer, III
1987 - Jonrob - John Storck, Jr.
1989 - Rabbit - Danirl P. Dyer, III
1991 - Nicole - T. Coleman duPont
1993 - Orion - Robert Norton
1995 - Nicole - T. Coleman duPont
1997 - Arrow - Bruce Lockwood
1999 - New Wave - Paul Hewitt
2001 - Sugar - Brad Parker
2003 - Zephyr - Roy Sherman
2005 - Chinook - Ed Austin
2007 - Cabady - Matt & Randy Baldwin
2009 - XLR8 - Brad Porter
2011 - Settler - Tom Rich
2013 - XLR8 - Brad Porter
2015 - Hustler - John & Tony Esposito
2017 - Rascal - Christopher Schineider
2021 - Deja Voodoo - William Zartler
2023 - Kenai - Chris Lewis