In 2003, Jimmy and his father Melvin Richardson were contracted to do the labor for building a tourist destination on empty land next to where an antique store stood. Over two years, Melvin and Jimmy worked to create three pavilions, a boardwalk, and a stage. They remodeled the inside of the house attached to the original building to extend the antique store rooms. After painting and mounting signs with historic decor, it became The Western Trail as an antique store with outdoor venue.

The Western Trail sits on the 66 Beltline, which was a bypass along Route 66 around the north to northwest side of Oklahoma City at Western and Britton Rd, established in 1931.  The venue debuted in 2005 and over time, the band enjoyed performing for the Western Trail Trade Days events. Jimmy's new band name became Jimmy Dale & The Beltline after a few slight band name changes and they became the only band to play the stage.  Articles and news segments  surrounding the story of the venue and it's live music with historical resurgence uplifted the scene and artists alike.

At the same time as the Richardson family worked on the Western Trail, they also remodeled the Owl Courts building. Owl Courts was built in the 1930s, shortly after the corner of Classen and Britton was named a Route 66 bypass around OKC.  In 2006, the office and original motor court behind it were in poor condition. Melvin and Jimmy were again contracted by John Dunning to bring it back to its original glory. They used salvaged vintage materials such as knotty pine tongue and groove boards for the walls and oak wood flooring as well as time period fixtures to  bring the building back as close as possible to an authentic motor court office from the 30s.