Let's Go to the Fair, by Island musician and Vineyard Gazette photographer Mark Alan Lovewell, was named Ag Fair Theme Song in the fair's first-ever awards for recorded music.

Special awards also went to Logan Camaranna's rendition of Twinkle, Twinkle, Little Star for Best Under 8 years and to fiddler Aidan Weiland's Irish Reel Set for the Best 8 to 16.

In the Best Original Song category, Tristan Israel won the blue ribbon for Monarch on Milkweed Leaving Aquinnah. Eric Mulhern took second place with Coalfire and Douglas Finn third for Once Upon a Time.

Best Cover Song awards went to Casey Hayward for her rendition of Sinéad O'Connor's Black Boys on Motorcycles and to composer Dean Rosenthal for a performance by two friends of his work Stones/Water/Time/Breath.

In the Spirit of the Island awards, Rachel Elion Baird took the blue ribbon for Island Girls, Jan Hulka the red for Perception and Luke Dunlap the white for Invisible Man.

Phil Spillane's Long Way Home, inspired by John Lewis and the Black Lives Matter movement, won the blue in the Song for 2020 category, followed by Rob Lytle's Pull Together and Richard Giaimo's Small Island.

In the category Almost Fair Famous, a cowboy-costumed video cover of Leon McAuliffe's Steel Guitar Rag from Ghost Island Farm won first place, followed by Skylar Hall's funk-flavored Mango Chutney and Rick Padilla's Choosing Love.

Self Accompanied Production awards went to Brian Weiland, who won blue for his cover of Janis Ian's Better Times Will Come; Sarah Piazza, with the red ribbon for her four-part adapatation of Babatunde Olatunji's Akiwowo and Paul Thurlow for his original Painting Again.

— Louisa Hufstader