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1989 Ken Smith (Deceased)
1989 Ginny Roach
1998 Leonard MacEwen
1998 Charlie Hansen
1998 Laurie Blue (Deceased)
1999 Ralph Kneabone (Deceased: 2005)
1999 Guy Cormier (Deceased)
2000 Glenda Johnston
2000 Gary Johnston
2001 Ivan Bulger (Deceased)
2003 Bob Sharples (Deceased)
2004 Bill MacEwen (Deceased)
2006 Alan MacRae (Deceased 2013)
2007 Bruce Martin
2009 Emery Gillan (Deceased)
2011 Francis & Vincent Cormier
2012 Andy Mooney
2017 Vans Bryant
2018 Audrey & John Barlow
2019 Shirley Smedley Jay
2022 Ann Hay
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Chesley MacDougall Award Recipients: This award is presented annually at the PEI Bluegrass & Old Time Music Festival, to the person who best exemplifies the spirit of Bluegrass & Old Time Music.
1987 Laurie Blue (Deceased)
1988 Leonard MacEwen
1989 Richard Roach (Deceased) / Helen Roach
1990 Charlie Hansen
1991 Guy Cormier (Deceased) & Janet MacEwen
1992 Glenda Johnston
1993 Ralph Kneabone (Deceased)
1994 Kris MacDougall
1995 Lem Roach (Deceased)
1996 Glenda Johnston
1997 Emery Gillan (Deceased)
1998 Eileen & Frank Brown
1999 Bluegrass Island – Hosts: Roger Wightman, Serge Bernard & Charlie Hansen
2000 Jericho Road – Marnie & Harold Noye, Emily & Vans Bryant, and David Miller
2001 Arnold Wagner
2002 Ivan Bulger (Deceased)
2003 Gary Johnston
2004 Yvonne Pitre & Al Pitre (Deceased)
2005 Alan MacRae (Deceased 2013)
2006 Shirley Smedley Jay
2007 Emery Gillan (Deceased)
2008 Bob Sharples (Deceased)
2009 Emily Bryant, Audrey Barlow, Edith Creighton, Shirley S. Jay (Cookbook Committee)
2010 Wayne Brown (Posthumously Awarded; Died 2010)
2011 Angela MacCormac
2012 John Barlow
2013 Albert Shepard
2014 Patricia MacKinnon
2016 Carolyn Jones
2017 Peter Richards
2018 Norman Bowser
2019 Wilson Moore
2022 Fern & Gerald Heustis
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