Windholme Trophies
Awarded annually to the Barrington Yacht Club yachts with the best elapsed time in Spinnaker Class and Cruising Class in the Spring Race (occasionally known as the Cuttyhunk Race). These trophies were given to the 2000 Club by Frederick T. Moses.
Spinnaker Class Winners
| 1954-55 | Lord Jeff | Charles Chapin |
| 1956-58 | Whisker | John R. Fales |
| 1959 | Lord Jeff | Charles Chapin |
| 1960 | Whisker | John R. Fales |
| 1961 | Lord Jeff | Charles Chapin |
| 1962 | Swizzle | E. Russell Davis |
| 1963-66 | Tango | Ernest H. McVay |
| 1967 | Banshee | Bob Almeida |
| 1968 | Quartette | Russell W. Field. Jr. |
| 1969 | Tango | Ernest H. McVay |
| 1970 | Mahi Mahi | William H. Shaw |
| 1971 | Demitasse | AJ Migliaccio |
| 1972 | Banshee | Bob Almeida |
| 1973-74 | Vamoose | W. Donald Wilson |
| 1975 | No Award Presented | |
| 1976 | Mariah | Charles V. Cox. MD |
| 1977-81 | Banshee | Bob Almeida |
| 1982 | Banshee | Bob Almeida |
| 1983 | Banshee | Bob Almeida |
| 1984 | No Award Presented | |
| 1985 | Banshee | Bob Almeida/John Dunn |
| 1986-89 | No Award Presented | |
| 1990 | Banshee | Bob Almeida |
| 1991 | Loose Cannon | John Dunn |
| 1992 | No Award Presented | |
| 1993-95 | Banshee | Bob Almeida |
| 1996 | Banshee | Bob Almeida |
| 1997 | Avanti | Vince Albee |
| 1998 | ||
| 1999 | ||
| 2000 | ||
| 2001 | ||
| 2002 | Who’s Your Daddy | Peter Manickas |
| 2003 | ||
| 2004 | No Award Presented | |
| 2005 | Falcon | Charles Stoddard |
| 2006 | No Award Presented | |
| 2007 | Falcon | Charles Stoddard |
| 2008 | No Award Presented | |
| 2009 | Falcon | Charles Stoddard |
| 2010 | No Award Presented | |
| 2011 | Falcon | Charles Stoddard |
| 2012 | Falcon | Charles Stoddard |
| 2013 | Falcon | Charles Stoddard |
| 2014 | No Award Presented | |
| 2015 | No Award Presented | |
| 2016 | Falcon 2.0 | Charles Stoddard |
| 2017 | Falcon 2.0 | Charles Stoddard |
| 2018 | epiphany | Nick Bowen |
| 2019 | Falcon 2.0 | Charles Stoddard |
| 2020 | Falcon | Charles Stoddard |
Cruising Class Winners
| 1956-57 | Tango | Ernest H. McVay |
| 1958 | Povanne | R. Read Shaw |
| 1959 | Dog Star | Prescott Gustafson |
| 1960 | Swizzle | E. Russell Davis, Jr. |
| 1961 | Nimbus II | Hugh S. Wagner |
| 1962 | Bean Blossom | Alan V. Young |
| 1963 | Chickasheen | George A. Matteson |
| 1964 | Bay Blue | John R. Fales |
| 1965-66 | Southerly | Charles F. Gladding |
| 1967 | Shady Lady | G. Richard Westin |
| 1968-69 | Vamoose | W. Donald Wilson |
| 1970 | Responde | William McGurk |
| 1971 | Vamoose | W. Donald Wilson |
| 1972 | Sunshine | A. Bryson Dawson |
| 1973 | Amee | John Lawson |
| 1974 | No Award Presented | |
| 1975 | Mahi Mahi | William Shaw |
| 1976 | Triumphe | Roger W. Spence |
| 1977 | Petrel | Julian Gibbs |
| 1978-80 | Triumphe | Roger W. Spence |
| 1981-82 | Mariah | Charles V. Cox, MD |
| 1983 | Nepenthe | Robert W. Read |
| 1984 | No Award Presented | |
| 1985-86 | Nepenthe | Robert W. Read |
| 1987 | Mariah | Charles V. Cox, MD |
| 1988-91 | Nepenthe | Robert W. Read |
| 1992 | Avanti | Vince Albee |
| 1993 | Nepenthe | Robert W. Read |
| 1994 | Orion | Robert Norton |
| 1995 | Nepenthe | Robert W. Read |
| 1996 | Nepenthe | Robert W. Read |
| 1997 | No Award Presented | |
| 1998 | Nepenthe | Robert W. Read |
| 1999 | ||
| 2000 | ||
| 2001 | ||
| 2002 | First Light | Andre Laus |
| 2003 | ||
| 2004 | No Award Presented | |
| 2005 | No Award Presented | |
| 2006 | No Award Presented | |
| 2007 | No Award Presented | |
| 2008 | No Award Presented | |
| 2009 | No Award Presented | |
| 2010 | No Award Presented | |
| 2011 | No Award Presented | |
| 2012 | Caneel | Chip Hawkins |
| 2013 | Caneel | Chip Hawkins |
| 2014 | Epiphany | Nick Bowen |
| 2015 | Epiphany | Nick Bowen |
| 2016 | Caneel | Chip Hawkins |
| 2017 | Caneel | Chip Hawkins |
| 2018 | Caneel | Chip Hawkins |
| 2019 | Caneel | Chip Hawkins |
| 2020 | No Award Presented |
