Lightfoot was born in Orillia, Ontario, to Jessie Vick Trill Lightfoot and Gordon Lightfoot, Sr., who owned a local dry cleaning business. He had one older sister, Beverley (1935-2017). His mother recognized Lightfoot's musical talent early on and schooled him into a successful child performer. His first public performance was "Too Ra Loo Ra Loo Ral" (an Irish lullaby) in grade four, which was broadcast over his school's public address system on a parents' day event. As a youth, he sang, under the direction of choirmaster Ray Williams, in the choir of Orillia's St. Paul's United Church. According to Lightfoot, Williams taught him how to sing with emotion and how to have confidence in his voice. Lightfoot was a boy soprano; he appeared periodically on local Orillia radio, performed in local operettas and oratorios, and gained exposure through various Kiwanis music festivals. At the age of twelve, after winning a competition for boys whose voices had not yet changed, he made his first appearance at Massey Hall in Toronto. As a teenager, Lightfoot learned piano and taught himself to play drums and percussion. He held concerts in Muskoka, a resort area north of Orillia, singing "for a couple of beers."