Trails and Rails is fronted by guitarist/mandolinist/banjoist Walt Richards, a native San Diegan whose career dates back to seeing Pete Seeger perform at Hoover High School in 1957, after which he formed the band Kensington 3. As of 2009, he lives and performs around North County, as well as teaching guitar, banjo, and mandolin at Old Time Music.

Singer/guitarist/mandolinist Paula Strong formerly played with Mandolin Madness. As of late 2009, both she and Richards also play in a 15-member swing band, the Brass Key and Wind.