At the annual meeting in January 1939, a Mr. Thomas B. McAdams proposed to the Board that the Society bestow, at an annual meeting one or possibly two suitable plaques or award to outstanding Virginians for meritorious accomplishments.  The Board approved this idea and authorized the President to appoint a committee to work out a definite plan.  In January 1940, the first Medallion of honor was presented to the Honorable Carter Glass, U.S. Senator from Virginia and posthumously to Dr. Wm. A. R. Goodwin. Hence forwarded a long-standing tradition of annually honoring at least one outstanding Virginian with a Virginians of Maryland Medallion was begun and remains so to this day.

In addition to honoring outstanding Virginians, at the annual meeting in 1945, the Society approved the sponsoring of an annual scholarship to be awarded to a high school graduate who will be attending a university in Virginia.  Both traditions of awarding of a Medallion to outstanding Virginians for meritorious accomplishments and a scholarship to a high school graduate who will be attending a university in Virginia remain today.

In addition to the above, the Virginians of Maryland have a long and distinguished tradition of providing great literary and other prominent, public persons a forum in which to impart their knowledge upon the group and others in the general public, so that we may all learn as a society.

• 2022 – Aubrey M. Daniel III
• 2020 – Dominic Dennis Starsia
• 2019 – Thomas F. Farrell, II
• 2018 – General John P. Jumper
• 2017 – S. Waite Rawls III
• 2016 – Dr. Edward L. Ayers
• 2015 – Haswell M. Franklin, Sr.
• 2014 – Alexander Brit Hume
• 2013 – George Catlett Marshall
• 2012 – John B. Adams, Jr.
• 2011- Dr. Gary W. Gallagher
• 2010 – John Casteen
• 2009 – G. Gilmer Minor III
• 2008 John Stewart Bryan III
• 2007 Oliver L. North
• 2006 William W. Berry
• 2005 Colonel John W. Ripley
• 2004 Coach Robert J. ‘Bobby’ Ross
• 2003 James W. Brinkley Background of James W. Brinkley
• 2002 Larry J. Sabato, Ph. D.
• 2001 Malcolm U. ‘Buck’ Pitt
• 2000 Roy Clark
• 1999 Dr. James I. Robertson, Jr.
• 1998 Earl Hamner
• 1997 Dr. Ronald E. Carrier
• 1996 George J. Collins
• 1995 Dr. Thomas Ransone Price
• 1994 John M. Barber
• 1993 Lewis B. Puller, Jr.
• 1992 General J. H. Binford Peay, III
• 1991 Augustus Robbins, III
• 1990 Raymond A. Mason
• 1989 James C. Wheat, Jr.
• 1988 Dr. H. Mebane Turner
• 1986 Frank L. Hereford, Jr.
• 1985 John O. Marsh, Jr.
• 1984 Josiah Bunting, III
• 1983 Lieutenant General Samuel V. Wilson
• 1982 Honorable Albertus S. Harrison, Jr.
• 1981 Robert B. Pamplin
• 1980 Honorable W. Graham Claytor, Jr.
• 1979 Honorable Lewis F. Powell, Jr.
• 1978 Dr. Robert Q. Marston
• 1977 Brigadier General Frank McCarthy
• 1976 John D. DeButts
• 1975 Senator Hugh Scott
• 1974 James Jackson Kilpatrick
• 1973 Honorable Mills G. Godwin, Jr.
• 1972 W. Thomas Rice
• 1971 E. Claiborne Robins
• 1970 Dr. Thomas G. Pullen Background of Dr. Thomas G. Pullen Jr.
• 1969 Dr. Christopher C. Kraft, Jr.
• 1968 Edward Hudson Lane
• 1967 Honorable Henry H. Fowler
• 1966 Major General George R. E. Shell
• 1965 Rear Admiral Charles S. Minter, Jr., U.S.N.
• 1964 Dr. Edgar F. Shannon, Jr.
• 1963 Frank Talbott, Jr.
• 1962 Robert H. Porterfield
• 1961 Virginius Dabney
• 1960 Senator A. Willis Robertson
• 1959 Harry Ashby Debutts
• 1958 Honorable William M. Tuck
• 1957 Lieutenant General Lewis B. Puller
• 1956 Dr. G. Foard McGinnis
• 1955 Reverend Dr. John Henry Day
• 1955 Honorable T. Coleman Andrews
• 1954 Honorable Walter S. Robertson
• 1953 General Lemuel C. Shepherd, Jr.
• 1952 Howard Bruce
• 1951 Admiral Lewis L. Strauss
• 1950 Thomas B. McAdams
• 1949 Governor Colgate W. Darden
• 1948 Admiral Richard E. Byrd
• 1947 Homer L. Ferguson
• 1946 Lady Nancy Astor
• 1945 Bishop Henry St. George Tucker
• 1944 Dr. Frederick W. Boatwright
• 1943 Senator Harry F. Byrd, Sr.
• 1942 John Stewart Bryan
• 1941 Dr. Douglas S. Freeman
• 1940 Senator Carter Glass
• 1940 Dr. Wm. A. R. Goodwin (Posthumously)