Lightfoot performed extensively throughout high school, Orillia District Collegiate & Vocational Institute (ODCVI), and taught himself to play folk guitar. A formative influence on his music at this time was 19th-century master American songwriter Stephen Foster. He was also an accomplished high school track-and-field competitor and set school records for shot put and pole vault, as well as being the starting nose tackle on his school's Georgian Bay championship winning football team. His athletic and scholarly aptitude earned him scholarships at McGill University's Schulich School of Music and the University of Toronto, Faculty of Music.