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As a boy soprano in Orillia, Lightfoot performed on local radio, in oratorio and operetta, in weddings across Southern Ontario and in Kiwanis Music Festivals. He appeared at age 13 in a concert of Kiwanis festival winners at Massey Hall, the site of many of his later triumphs. In 1952, he won first place in the "soprano unchanged voices" class at the Kiwanis Festival.

At 14, Lightfoot began working at his father’s dry cleaning plant, where he worked throughout high school. In his teens, he was a star track and field athlete and played on the school football team. He also studied piano, taught himself to play drums and sang in a barbershop quartet called The Collegiate Four. In 1954, The Collegiate Four won first prize in a CBC Television talent competition called Pick the Stars. Lightfoot also won several competitions with the quartet the Teen-Timers in 1955.

? ?, 1951 (Kiwanis Music Festival. Gordon placed first in the solo class for boys under 13, and third in boys with unchanged voices, after performing "Alpine Song" & "Under the Greenwood Tree")

? ?, 1952 (Kiwanis Music Festival. Gordon placed first in the Boys, Unchanged Voices vocal category after performing "Who is Sylvia?" accompanied By Mary Wedlock on piano)

? ?, 1952 Massey Hall, Toronto, ON (As a result of his performance at the Kiwanis Music Festival, he was among those chosen to perform at a "Stars Of The Festival" grand concert)

December ?, 1955 Barbershop quartet, The Teentimers, with 17 year old Baritone Gordon Lightfoot, placed 2nd in an Ontario competition.

From 1959 to 1961, he appeared on CBC TV's variety show "Country Hoedown" with the groups the Singing Swinging Eight and the Gino Silvi Singers.

1962

In 1962, he teamed up with Teen-Timers member Terry Whalen and performed as the Two Tones in Southern Ontario coffee houses. The pair released a live LP domestically titled Two Tones at the Village Corner in 1962 and performed at the Mariposa Folk Festival that year.

January 20, 1962 Village Corner, Toronto, ON (live album recorded)

​Orillia, ON (Mariposa Folk Festival)

1963

In 1963, Lightfoot went to Europe and served for one season as the host of BBC TV's "Country and Western Show", staying in England for five months. Upon his return to Canada, he appeared in coffee houses and bars in Ontario, Québec and the eastern United States.

Fall 1963 ​​Clef, Toronto, ON

Fall 1963 ​​Embassy, Toronto, ON

​Fall 1963 ​Corner, Toronto, ON

​Fall 1963 ​Purple Onion, Toronto, ON

​Fall 1963 ​Village Gate, Toronto, ON

​Fall 1963 ​Fifth Peg, Toronto, ON

​Fall 1963 ​Gates of Cleve, Toronto, ON

​Fall 1963 ​The Cellar, Toronto, ON

Fall 1963 ​​Steeles Tavern, Toronto, ON

1964

? ?, 1964 ​Downstairs Club, Hamilton, ON

? ?, 1964 ​Riverboat, Toronto, ON

January ?, 1964 Steeles Tavern, Toronto, ON (over 30 gigs over 3 years)

? ?, 1964 Teachers College, Toronto, ON (performed all his material, no covers)

​? ?, 1964 Maple Leaf Stadium, Toronto, ON (Mariposa Folk Festival)

Fall 1964 Purple Onion, Toronto, QC

1965

June ​8-20, 1965 Riverboat, Toronto, QC

July 6-18, 1965 ​La Cave, Cleveland, OH

July 25, 1965 ​(Newport Folk Festival 1965)

August 6-8, 1965 Innis Lake Campground, Caledon East, ON (Mariposa Folk Festival. Unsure which day Gordon performed)

August ?, 1965 Mother Blues, Chicago, IL (2 week engagement)

September​ 3, 1965 NBC Studio 6B, New York City, NY (US TV "Johnny Carson’s Tonight Show" performing "Early Morning Rain")

Fall 1965 ​L'Hibou, Ottawa, ON

Fall 1965 Chess Mate, Detroit, MI

​Fall 1965 ​The Second Fret, Philadelphia, PA

? ?, 1965 ​The Inn, Philadelphia, PA

​? ?, 1965 ​Living End, Detroit, MI

? ?, 1965 ​​Gerde’s Folk City, New York City, NY

​? ?, 1965 ​Gaslight South, Miami, FL

​? ?, 1965 ​Le Cave, Cleveland, OH

October 11-16, 1965 ​Odyssey, Boston, MA

October ?, 1965 New Gate Of Cleve, Yorkville, ON (week engagement)

November 9-26, 1965 Raven Gallery, Southfield, MI

November 27, 1965 Town Hall, New York City, NY (supporting Paul Butterfield Blues Band & Jim Kweskin Jug Band)

1966

January 18, 1966 Toronto, Riverboat (Start of a two week engagement)

February ?, 1966 De Montfort Hall, Leicester, ENG

February ?, 1966 Fairfield Hall, London, ENG

February ?, 1966 Varsity Stadium, Toronto, ON

March ?, 1966 Queen Elizabeth Theatre, Toronto, ON (1966 Easter Seal Show (20th annual coast to coast benefit variety show), hosted by Bing Crosby. Broadcast March 27th)

April 1-10, 1966 Living End, Detroit, MI

May ?, 1966 Riverboat, Toronto, ON

June ?, 1966 Riverboat, Toronto, ON (month engagement)

? ?, 1966 ​L'Hibou, Ottawa, ON

​Mariposa Folk Festival

July 23, 1966 Central Park Wollman Skating Rink Theater, New York City, NY (Rheingold Central Park Music Festival 1966)

July 27, 1966 Cafe Au Go Go, New York City, NY

August 24-28, 30-September 4, 1966 Living End, Detroit, MI

September 23-25, 1966 Canterbury House, Ann Arbor, MI

? ?, 1966 Northern Jubilee Auditorium, Edmonton, AB

November 4-6, 1966 Main Point, Bryn Mawr, PA

? 1966/1967 Privateer Coffee House, Halifax, NS

1967

Spring 1967 Campion High School's Boyle Gym, Regina, SK

January 3-29, 1967 Riverboat, Toronto, ON

February 3, 1967 University Of Windsor, Windsor, ON

February 4, 1967 Dalhousie University, Halifax, NS

February 11, 1967 Queen's University, Kingston, ON

March 3, 1967 Lutheran University, Waterloo, ON

March 16-19, 1967 Main Point, Bryn Mawr, PA (with Chip Bond)

March 22-26, 1967 Living End, Detroit, MI

March 31, 1967 Massey Hall, Toronto, ON (first Massey Hall concert)

April 3-7, 1967 Club 47, Cambridge, MA

May 8-15, 1967 Canadian Pavilion, Montreal, QC (Expo '67)

May 18-21, 1967 The New Penelope, Montreal, QC

​? ?, 1967 Quebec Pavilion

July 3-15, 1967 Riverboat, Toronto, ON

September 14, 1967 University Hall, Wolfville, NS

1968

January 13, 1968 Waterloo Lutheran University Theatre Auditorium, Waterloo, ON

February 13-18, 1968 Unicorn, Boston, MA

March 1-3, 1968 Harbour Lights, Ecorse, MI (supported by Jan & Lorraine)

March ?, 1968 Massey Hall, Toronto, ON (2 shows)

March 18, 1968 Canadian TV "Wherefore and Why" CBC TV Special

April 2-7, 1968 Troubadour, Los Angeles, CA

April 19-20, 1968 San Diego Folk Festival

April 26-28, 1968 San Francisco State College, San Francisco, CA (San Francisco State 7th Annual Folk Festival)

May 7-13, 1968 Place Des Arts, Montreal, QC

May 10, 1968 Theatre Maisonneuve Place des Arts, Montreal, QC

May 18, 1968 Cobourg District Collegiate Institute East, Cobourg, ON (2 shows 2.00 & 8.00)

May 20-25, 1968 Cellar Door, Washington, DC

June 5, 1968 Bitter End, New York City, NY (with Ruan McKinnon)

September 24-29, 1968 Troubadour, Los Angeles, CA

October 3-5, 1968 Fillmore West, San Francisco, CA (supporting Canned Heat, with Cold Blood)

October 7, 1968 Theatre Maisonneuve Place des Arts, Montreal, QC

October ?, 1968 Seattle, WA

October ?, 1968 Pocatello, ID

? ?, 1968 ​US TV "Johnny Cash show"

1969

January 18, 1969 Willamette University Fine Arts Auditorium, Salem, OR

March 29-31, 1969 Massey Hall, Toronto, ON (4 shows)

April 5, 1969 Place Des Arts, Montreal, QC

April 26, 1969 Brown University's Pembroke Field, Providence, RI (Brown Spring Weekend '69)

May 3 or 4, 1969 Soledad Canyon (Country Pop Festival)

June 2, 1969 Royal Festival Hall, London, ENG

August 8, 1969 Hollywood Bowl, Los Angeles, CA (supporting Peter, Paul & Mary)

November 21, 1969 Ford Auditorium, Detroit, MI

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