*1960*
- He begins work as a choral performer and dancer on CBC's Country Hoedown, and would continue working there for more than two years.
- Became interested in folk music through listening to Bob Gibson and in particular, the Weavers At Carnegie Hall album.
- Around this time he switched from the 4-string tenor guitar to the conventional 6 and 12-string guitars. Within a year he was proficient enough to perform professionally.
- As a member of the Two Tones, Lightfoot undertakes a series of recording sessions in Toronto. (Read More...)

*1961*
- Plays drums for a revue called Up Tempo '61.  He plays under the pseudonym Charles Sullivan.
- The first Mariposa Folk Festival is held.  The Two Tones are not invited because they are deemed to be too commercial!
- Lightfoot makes his US debut at La Cave in Cleveland, sharing the bill with Jose Feliciano.

*1962*

- In January he records a live album at Toronto's Village Corner as a member of the folk duo, the Two Tones, with partner Terry Whelan. (Read More...)
- Remember Me (I'm The One) reaches the top 10 on the Canadian charts.

*1963*
- Appeared in Orillia in January at a teen dance at the Pavalon Club with a Toronto singing group called the Dovermen.
- In April Lightfoot marries Brita in Sweden.
- Hosted 8 one-hour summer replacement shows in England for the BBC called "Country And Western."

*1964*
- Lightfoot becomes influenced by Dylan.  Although he'd written 75 songs prior to that time, they didn't contain an "identity."  His writing now begins to flourish. (Read More...)
- He writes Early Morning Rain on a hot summer afternoon.
- Ian & Sylvia come to Steele's Tavern in Toronto to hear Lightfoot and come away very impressed.  They eventually record some Lightfoot songs which leads to Lightfoot being signed by the influential Albert Grossman management agency from New York.
- Peter, Paul and Mary's recording of For Lovin' Me reaches the US top 20.
- Lightfoot plays the Toronto Teacher's College.  The significance of this show was that it marked the first time he had done an entire show of his own material.
- In December, he records the tracks for his debut album for United Artists in a New York Studio.

*1965*

- Appears at the prestigious Newport Folk Festival and is there when Dylan goes "electric". (Read More...)
- Lightfoot makes the 18 hour train trip to Moosenee in northern Ontario on the shore of James Bay and the journey inspires Steel Rail Blues.
- When Lightfoot was signed to WB's in 1965 a party was held for him at Steele's Tavern - sandwiches courtesy of WB's, beer courtesy of Steele's.
- He lived for a time in Detroit near Wayne State University at Joni and Chuck Mitchell's apartment and performed at area clubs like Chess Mate.
- Makes an appearance on the Tonight Show.
- Marty Robbins' recording of Ribbon Of Darkness spends 7 months on the C&W charts, reaching #1, and wins the ASCAP writer-publisher award.
- Red Shea and John Stockfish are recruited as Lightfoot's touring and recording band. (Read More...)
- In November he makes his New York debut at the Town Hall.
- On November 13, the Yarmouth Castle catches fire and sinks off of Miami.

*1966*

- In January, Lightfoot! is released by United Artists.
- In February he draws 3,500 to Varsity Stadium in Toronto.
- In February he completes a nine city tour of the British Isles with Ian & Sylvia, beginning at the De Montfort Hall in Leicester and finishing up at the Fairfield Hall in London.
- In May he completes a successful run at Toronto's Riverboat coffeehouse. (Read More...)
- Lightfoot is commissioned by the CBC to write a song about the building of the Canadian railway for Canada's centennial.  The result is of course, Canadian Railroad Trilogy.

*1967*
- On New Year's day, Lightfoot debuts the Trilogy across the country on the CBC-TV special, 100 Years Young.
- In January, he completes a month-long engagement at the Riverboat.
- In March, Lightfoot plays two sold-out concerts at Massey Hall.
- In the spring, The Way I Feel is released.

*1968*
- A Lightfoot special is aired on CBC on March 18.
- In March, two more sold-out performances at Massey Hall.
- Did She Mention My Name is released.
- Lightfoot makes a "writng" trip to England where he composes poetry and the songs that will comprise his next album.
- In May, he makes his first San Francisco appearance at the SF State College Folk Festival.
- Lightfoot does a spring tour of Ontario.
- Lightfoot plays a week engagement at the Cellar Door in Washington DC.
- Lightfoot does 9 concerts with Peter, Paul and Mary at venues such as the Hollywood Bowl.
- Lightfoot records Back Here On Earth in Nashville in September.
- Appears at the Troubadour in LA and the Fillmore in San Francisco.
- Back Here On Earth is released.
- Lightfoot appears at a sold-out concert at the University Of Toronto.
- Appears for a second time at New York's Town Hall, this time as the headlining act. (Read More...)

*1969*

- Early Morning Productions are formed to manage Lightfoot's affairs, with Al Mair hired as general manager.
- Four Massey Hall concerts are recorded in March and are released later in the year as Sunday Concert.
- Lightfoot records in Nashville in April but no tracks are ever released from these sessions.  These became known as the "33rd Of August" sessions, after the Mickey Newbury song that was recorded during them.
- Appears as a solo act for the first time on a British stage with an appearance at London's Royal Festival Hall. (Read More...)
- In November, Lightfoot signs with Warner Brothers Records to record on their Reprise label, signalling the end of the 60's and his United Artists years.