Presented in memory of Past Commodore Hugh Kilmer and rededicated in 2026, this trophy is awarded to the best-performing yacht 30 years of age or older, sailing exclusively in a handicap class, as determined by the Organizing Authority at Block Island Race 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
2025 - Blitzen - John Storck, Jr.