Conley started as a Harry Belafonte-style calypso singer at the Windsor Hotel in Denver. “I was barefooted and wearing cut-off pants,” he remembered on the Walt Conley & Company website. “It was a crazy way to perform.” By 1958, he was appearing at Colorado venues including the Red Ram in Georgetown and Little Bohemia in Denver, where he met Judy Collins, who suggested that he play at Michael’s Pub in Boulder.
In 1959, Hal Neustaedter opened the Exodus in the Raylane Hotel, bringing premier folk acts to Denver. According to Fritz, “On October 16, 1959, the Exodus hosted…Denver’s first Folk Music Festival. Josh White was the headliner. The line-up included Walt Conley, Judy Collins, the Harlin Trio, George Downing, The Travelers, and Dave Wood among others.” A recording, Folk Festival at the Exodus, was made of the event; on it, Conley sings “900 Miles,” “Worried Man Blues,” “Passing Through” and “John Henry.”
Around this time, Conley was asked to take over booking at the Satire Lounge; he reportedly booked the Smothers Brothers for their first Denver appearance and gave Bob Dylan a place to stay at his house near the club.