The son of a Scottish immigrant father and a Mi'kmaq aboriginal mother, Don was born in Montreal in 1960 into a musical family. He first started experimenting with the solo possibilities of the acoustic guitar at the age of eight. By age ten he was playing in alternate tunings and exploring "fingerstyle" technique, a right hand discipline similar to classical guitar playing. Preferring to write original music and develop a personal style, Don's self-taught journey on the instrument has encouraged him to follow his musical intuition. The result is an unclassifiable musical style that borrows from jazz, folk, rock and classical music. When asked, Don usually pigeonholes his music as "Heavy Wood"!

Don graduated from the Music Department of Toronto's York University in 1983, but waited until 1986 to start pursuing a career as a performer. After his first win at Winfield, Don was asked to sign with Duke Street Records. He recorded three CDs for Duke Street over the course of the next four years: Bearing Straight, Don Ross and Three Hands. The CDs met with unanimous critical acclaim and numerous tours across Canada and the U.S. Don even played at the Montreux Jazz Festival in Switzerland.

Don signed a new recording deal with Columbia/Sony Music in 1994, releasing his first album for the label, This Dragon Won't Sleep, in 1995. In the fall of 1996 Don released Wintertide, an instrumental album of traditional Christmas tunes played in his trademark style. Lynn Saxberg of the Ottawa Citizen called the CD a "masterpiece," and the public response was no less enthusiastic. Don's next record, Loaded. Leather. Moonroof. was released in November, 1997. The album "...is a further exploration for a rich sense of harmony and groove," according to Don. The CD treats Don's listeners to a compilation of diverse sounds that reflects his influence by all types of music. On this album, Don passionately plays the six-string and seven-string guitars as well as the dobro. He is often accompanied by several other musicians whom all add their specialty. Don considers the first track, "Loaded. Leather. Moonroof." one of the most powerful tunes he has recorded to date, due partly to a great solo by bassist Mark Egan, who asked to play with Don that year. Mark's previous work includes collaborations with guitar great Pat Metheny, singer Joan Osbourne and countless others. The collection of tunes on Loaded. Leather. Moonroof. carries Don further past the usual style boundaries associated with acoustic music.