Turning onto westbound West Jefferson Street from S Monroe St/US 27, the route cuts southwest around the Florida State Capitol.

It passes by the Donald L. Tucker Center and the southern edge of Florida State University's main campus.

Along the same stretch, W St. Augustine Rd serves as the one-way eastbound carrier of Route 366, two blocks to the south of Pensacola St.

Further to the west, there are several municipal services, including the Leon County School Board and a fire department training center, as well as a homeless shelter.

It then passes over the Florida Gulf & Atlantic railroad line on an overpass before meeting its western terminus at SR 20 In Tallahassee.