The Donald Richardson deLoriea Memorial Trophy was given in memory of a former treasurer of the Pleon Yacht Club, who also served as a trusted friend and advisor of the Pleon with Arthur Goodwin Wood and Henry Appleton Knowles during the pre-war era.
It is competed for each season on corrected time in the annual Chowder Race of the Pleon Yacht Club over a long distance course of not less than 12 miles that tests the junior skippers in coastwise navigation. It is open to suitable yachts of less than 16-feet waterline length and the helmsman must be a member of the Pleon Yacht Club.
The names of the winning yacht and its owner are inscribed on the deLoriea Memorial Trophy Shield, which remains in the possession of the winning owner through the ensuing year. A suitable permanent prize is also awarded to the owner of each winning yacht.
1928 Phantom, Class O, C. Cushman Clapp, Jr.
1928 Shark, Class T, Albert Boodhue, Jr.
1929 Sea Beast II, Class T, John J.Perkins, Jr.
1930 Chandra, Star Class, Jeanie Paine
1931 Rita H., Star Class T, Paul Jacobs
1932 Ilex, Class T, Willliam T. Haley Jr.
1933 Bandit, Class T, Arthure J. Santry, Jr.
1934 Small Fry, Class T, Bud Boutwell
1935 Formosa, Class T, David O. Ives and Robert C. Seamans, Jr.
1936 Sabrina, Class T, Lorne MacKinnon
1937 Sabrina, Class T, George D. O'Day
1938 Mons Meg, Town Class, Clinton McKim
1939 Good News Too, Town Class, George D. O'Day
1941 Vincemus, 110 Class, George D. O'Day
1942 Dorset, 110 Class, Gerry Tierney
1943 Wis-By, Snipe Class, Byron Wiswell
1944 Aero, 110 Class, Bruce Hood
1945 No Competition
1946 The Reason?, 110 Class, Edwin C. Stephenson and John H. Blodgett Jr.
1947 Victory, 110 Class, Donald W. and John H. Blodgett, Jr.
1948 Ragamuffin, 110 Class, Grace Loring
1949 Arundel, 110 Class, John B. Newhall, II
1950 Tinker Too, 110 Class, Phillip Tierney and Thomas V. Loring
1951 Lady Luck, 110 Class, Randolph P. Barton
1952 Calypso, 110 Class, Thomas Townsend and John B. Newhall
1953 Swifty II, 110 Class, Gengean Keating
1954 Swifty II, 110 Class, Gengean Keating
1955 Swifty II, 110 Class, Gengean Keating
1956 Storm Trysail, 110 Class, Richard M. Barton and Stephen C. Newhall
1957 Black Mariah, 110 Class, Jonathan Wales and Stephen Newhall
1958-59 No Competition
1960 Thomas Bernard
1961 No Competition
1962 Flying Dutchman, 110 Class, Nicholas Kip
1963 Black Magic, 110 Class, David Curtis
1964 Sundowner, 110 Class, Alan Bell
1965 Kippecanoe, 110 Class, Kip Curtin
1966 Winston, 110 Class, William Owens
1967 No Competition
1968 210 Class, Lawrence Burkmeyer
1969 Feather, Soling Class, J. Kenneth Baxter, Jr.
1970-1972 No Competition
1973 Bonnie Wiencke, 470 Class
1974 Peter Fernberger, Laser Class
1975-1978 No Competition
1979 Rob Hallawell, 420 Class
1980-1997 No Competition
1998 Sean Leake and Colin Fraser, JY 15
1999 Jamie Leake and R. Hawkins, JY 15
2000 Robbie Gorman and Jamie Leake, JY 15
2001 Grace Bacon and Michelle Tariverdian JY15
2003 Justin Forster , John Howie and Josh Sargent JY15
2003 Annie Boldys and Katie St. George JY 15
2004 Robbie Gorman and crew Viper 640