Edgartown Yacht Club Regatta
Winners of First Day
| Year | Yacht | Skipper |
| 1928-1953 | No Record | |
| 1954 | Roweida VII (95) | Gordon Beggs |
| 1955 | Quip (101) | Lee Hunter |
| 1956 | Hermanos (76) | Allan L. Priddy |
| 1957 | Bettayet (117) | Ross W. Richards |
| 1958 | Dungolphin (109) | Durban A. McGraw |
| 1959 | Marna (120) | John T. Fallon |
| 1960 | Marna (120) | John T. Fallon |
| 1961 | Marna (120) | John T. Fallon |
| 1962 | Nonchy (65) | J.W. Scarborough, Jr. |
| 1963 | Venture (85) | David D. Steere |
| 1964 | Marna (120) | John T. Fallon |
| 1965 | Venture (85) | David D. Steere |
| 1966 | Sovereign IV (83) | Harrison P. Bridge |
| 1967 | Marna (120) | John T. Fallon |
| 1968 | Marna (120) | John T. Fallon |
| 1969 | Bettawin (141) | Ross W. Richards |
| 1970 | Bettawin (141) | Ross W. Richards |
| 1971 | No Record | |
| 1972 | Bettawin (141) | Ross W. Richards |
| 1973 | Pertelote (143) | Boardman Lloyd |
| 1974 | Pertelote (143) | Francis V. Lloyd, III |
| 1975 | Pertelote (143) | Boardman Lloyd |
| 1976 | Victura (167) [194] | Joseph P. Kennedy, II |
| 1977 | Cirrus (136) | George P. Edmonds, III |
| 1978 | Invader (169) | Lewis J.H. Gunn |
| 1979 | Invader (169) | Lewis J.H. Gunn |
| 1980 | No Record | |
| 1981 | Madeline (148) | Richard W. Burnes, Jr. |
| 1982 | Victura (167) [194] | Edward M. Kennedy, Jr. |
| 1983 | Pertelote (143) | Francis V. Lloyd, III |
| 1984 | Cirrus (136) | George P. Edmonds, III |
| 1985 | Cochenoe (125) | Donald F. Law, Jr. |
| 1986 | Marna (120) | John T. Fallon, Jr. |
| 1987 | Invader (174) | Lewis J.H. Gunn |
| 1988 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1989 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1990 | Scarlet (163) [173] | Thomas H. O’Toole |
| 1991 | Eight Ball (142) | Karl E. Anderson |
| 1992 | Cirrus (136) | Alden Edmonds |
| 1993 | Molly (158) | John T. McDonough |
John T. Fallon Trophy
Presented by the Class Association in Honor of John T. Fallon
| Year | Yacht | Skipper |
| 1994 | Touch o’ Gray (180) | Lee S. Williams |
| 1995 | Eight Ball (142) | Karl E. Anderson |
| 1996 | Cirrus (136) | Holly Edmonds |
| 1997 | Eight Ball (142) | Karl E. Anderson |
| 1998 | Rapparee (177) | Peter L. O’Keeffe |
| 1999 | Chanzia (157) | Lloyd M. McManus, Jr. |
| 2000 | Yankee Dime (145) | Alden Edmonds |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Yankee Dime (145) | B. Francis Saul |
| 2003 | Eowyn (169) | George Largay |
| 2004 | Lindy (182) | David McDonough |
| 2005 | Aurora (200) | Holly Edmonds |
| 2006 | Cochenoe (197) | John Kiley |
| 2007 | Heritage (199) | John T. Fallon, Jr. |
| 2008 | Cochenoe (197) | Donald F. Law, Jr. |
| 2009 | Mad Jack (206) | Jack Hamilton |
| 2010 | Mad Jack (206) | Jack Hamilton |
| 2011 | Mad Jack (206) | Jack Hamilton |
| 2012 | Smoke (214) | Richard Feeny |
| 2013 | Beltane (222) | Jim Cunningham |
| 2014 | Heritage (199) | John T Fallon, Jr. |
| 2015 | Smoke (214) | Joe Lotuff |
| 2016 | Aurora (200) | Holly Edmonds |
| 2017 | Heritage (199) | John T Fallon, Jr. |
| 2018 | Mad Jack (206) | Jack Hamilton |
| 2019 | Madeline (207) | Eli and Henry Burnes |
| 2020 | Smoke (214) | Joe Lotuff |
| 2021 | Race abandoned | |
| 2022 | Kerplunk (225) | Kent Plunkett |
| 2023 | Aria (213) | Peter Shope |
| 2024 | Aria (213) | Peter Shope |
| 2025 | Patience (179) | Ben Blum |
Winners of the Second Day
| Year | Yacht | Skipper |
| 1928-1953 | No Record | |
| 1954 | Sea Dog(8) | Heywood Fox |
| 1955 | Bettayet (117) | Ross W. Richards |
| 1956 | Hermanos (76) | Allan L. Priddy |
| 1957 | Bettayet (117) | Ross W. Richards |
| 1958 | Ebb (56) | A. Leighton |
| 1959 | No Record | |
| 1960 | Sovereign IV (83) | Harrison P. Bridge |
| 1961 | Ebb (56) | George Rockwood |
| 1962 | Venture (85) | David D. Steere |
| 1963 | Hermanos (76) | Allan L. Priddy |
| 1964 | Marna (120) | John T. Fallon |
| 1965 | Marna (120) | John T. Fallon |
| 1966 | Uncle Benny (73) | Stanley W. Moore |
| 1967 | Marna (120) | John T. Fallon |
| 1968 | Marna (120) | John T. Fallon |
| 1969 | Race Abandoned – Light Air | |
| 1970 | Bettawin (141) | Ross W. Richards |
| 1971 | No Record | |
| 1972 | Marna (120) | John T. Fallon |
| 1973 | Cirrus (136) | George P. Edmonds, Jr. |
| 1974 | Pertelote (143) | Francis V. Lloyd, III |
| 1975 | Pertelote (143) | Boardman Lloyd |
| 1976 | We’re Here (129) | Connie M. Tracy |
| 1977 | Molly (158) | Alan T. McDonough |
| 1978 | Madeline (148) | Richard M. Burnes, Jr. |
| 1979 | Cirrus (136) | George P. Edmonds, Jr. |
| 1980 | Cirrus (136) | George P. Edmonds, Jr. |
| 1981 | Molly (158) | Alan T. McDonough |
| 1982 | Venture (85) | David D. Steere |
| 1983 | Victura (167) [194] | Edward M. Kennedy, Jr. |
| 1984 | Race Not Scored | |
| 1985 | Snow Goose (161) | Lewis J.H. Gunn |
| 1986 | Cochenoe (125) | Donald F. Law, Jr. |
| 1987 | Victura (167) [194] | Edward M. Kennedy, Jr. |
| 1988 | Intuition (147) | James H. Light |
| 1989 | Cochenoe (125) | Donald F. Law, Jr. |
| 1990 | Eight Ball (142) | Karl E. Anderson |
| 1991 | Lucky Lady (172) | Bradford W. Tracy |
| 1992 | Eight Ball (142) | Karl E. Anderson |
| 1993 | Cirrus (136) | Holly Edmonds |
David D. Steere Trophy
Presented to the Class Association in Memory of
David D. Steere by the Steere Family
| Year | Yacht | Skipper |
| 1994 | Invader (184) | Lewis J.H. Gunn |
| 1995 | Eight Ball (142) | Karl E. Anderson |
| 1996 | Race cancelled – High Winds | |
| 1997 | Lente Festina (184) | G. Kent Plunkett |
| 1998 | Cirrus (136) | Holly Edmonds |
| 1999 | Lente Festina (184) | G. Kent Plunkett |
| 2000 | Yankee Dime (145) | Alden Edmonds |
| 2001 | Pieces of 8 (188) | Karl E. Anderson |
| 2002 | Yankee Dime (145) | B. Francis Saul, III |
| 2003 | Pieces of 8 (188) | Todd Kittredge |
| 2004 | Pieces of 8 (188) | Todd Kittredge |
| 2005 | Pieces of 8 (188) | Todd Kittredge |
| 2006 | Pieces of 8 (188) | Todd Kittredge |
| 2007 | Eowyn (202) | George Largay |
| 2008 | Cochenoe (197) | Donald F. Law, Jr. |
| 2009 | Eowyn (202) | George Largay |
| 2010 | Pieces of 8 (188) | Heather Gregg |
| 2011 | Eowyn (202) | Tim Wadlow |
| 2012 | Smoke (214) | Richard Feeny |
| 2013 | Beltane (222) | Jim Cunningham |
| 2014 | Mad Jack (206) | Jack Hamilton |
| 2015 | Mad Jack (206) | Jack Hamilton |
| 2016 | Scout (220) | Kelsey Wheeler |
| 2017 | Madeline (207) | Henry Burnes |
| 2018 | Madeline (207) | Henry Burnes |
| 2019 | Kerplunk (225) | Kent Plunkett |
| 2020 | Scout (220) | Fraser Pesek |
| 2021 | Smoke (214) | Jack Howard |
| 2022 | Smoke (214) | Clark Lotuff |
| 2023 | Not Sailed | High Winds |
| 2024 | Three Sticks (212) | Peter McAvoy |
| 2025 | Scout (220) | John Fallon |