The Freight Hoppers assembled in the mid-'90s around Cary Fridley's singular voice, drawing inspiration from old-time music of the 1920s and 1930s, with Fridley herself later pursuing a separate solo career. Roots of the band trace to the early '90s, when Atlanta-born banjoist Frank Lee performed aboard the Great Smokey Mountain Railway in Bryson City, North Carolina. Lee summoned Cleveland-raised fiddler David Bass, who had previously busked through New York City and New Orleans, to assist with entertaining passengers who had just disembarked. Kentucky native Cary Fridley, working as a schoolteacher in Mocksville, North Carolina, encountered Lee at a social gathering; she soon abandoned her teaching post to become the group's vocalist and guitarist. Upstate New York acoustic bassist Jim O'Keefe joined after crossing paths with the others at Merlefest in North Carolina.
Once fully formed, the Freight Hoppers took up regular performances along the Bryson City railway line each year from Memorial Day until October. National attention arrived in March 1996 after the quartet won the Talent From Towns Under 2,000 competition—selected from nearly 500 applicants—and appeared on Garrison Keillor's celebrated National Public Radio program A Prairie Home Companion. Their first release, the 1996 Rounder Records album Where'd You Come From, Where'd You Go?, drew on traditional standards from the 1920s and 1930s. A comparable follow-up, Waiting on the Gravy Train, appeared in 1998. Fridley issued her solo effort Neighbor Girl three years later.
