Cuttyhunk Trophy
Awarded to the winner of the Cuttyhunk Race for Cruising Class.
| Winners | ||
| 1964 | Hornpipe | Ernest N. Swanson |
| 1965 | Sasu | John Elliot |
| 1966 | Marango | Adelbert A. Goff |
| 1967 | Curlew | Frederick W. Thomas |
| 1968 | Fleetwing | Henry P. Eldredge |
| 1969 | Hornpipe | Ernest N. Swanson |
| 1970 | Jena | Charles A. LaRoue |
| 1971 | Lone Ranger | David Giuliano |
| 1972 | Nepenthe | Robert W. Read |
| 1973 | Spot | Dick Fales |
| 1974 | Skal | Gordon Hagglund |
| 1975 | Keewaydin | Ken Weller |
| 1976-77 | Teal | Bruce Ferguson |
| 1978 | Bagpiper | Richard Duncan |
| 1,979 | Sugarfoot | John Westbrook |
| 1980 | Aurora | James Young |
| 1981 | Ralph Rotten | John Lavin |
| 1982 | Petrel | Julian Gibbs |
| 1983 | Petrel | Cora Lee Gibbs |
| 1984 | No Award Presented | |
| 1985 | Rabbit | Dan and Mimi Dyer |
| 1986-89 | Wings | Irving Sheldon |
| 1990 | Spunky | Philip Hecht |
| 1991 | Wings | Irving Sheldon |
| 1992 | Wandelaar | Nic Van Dongen |
| 1993 | No Award Presented | |
| 1994 | Wandelaar | Nic Van Dongen |
| 1995 | Rabbit | Dan & Mimi Dyer |
| 1996 | Bizzy Ball | Thomas Heald |
| 1997 | Wandelaar | Nic Van Dongen |
| 1998 | No Award Presented | |
| 1999 | No Award Presented | |
| 2000 | No Award Presented | |
| 2001 | No Award Presented | |
| 2002 | No Award Presented | |
| 2003 | No Award Presented | |
| 2004 | No Award Presented | |
| 2005 | Polaris | Peter Northup |
| 2006 | Wild Goose | Tom McLaughlin |
| 2007 | No Award Presented | |
| 2008 | Tamerlane II | Joseph Roszkowski |
| 2009 | No Award Presented | |
| 2010 | No Award Presented | |
| 2011 | No Award Presented | |
| 2012 Around Aquidneck | Clank | Joe Bovin |
| 2013 Around Aquidneck | Serendipity | Gary Venable |
| 2014 Around Aquidneck | Bramasole | Bob Catani |
| 2015 | Serendipity | Gary Venable |
| 2016 | Serendipity | Gary Venable |
| 2017 | Arigato | Thomas Gieseke |
| 2018 | Serendipity | Gary Venable |
| 2019 | Epiphany | Nick Bowen |
| 2020 | Serendipity | Gary Venable |
