Bolivar is graced with three distinct historic districts. The North Main District contains more than 20 homes, originating from dates that span from the 1840s to the 1940s, and representing many architectural styles. The Court Square District includes the 1868 courthouse, as well as one of the only three log courthouses left in the U.S. The Bills-McNeal Historic District contains several outstanding antebellum mansions.

The districts include the following sites:

• McNeal House (1856) designed by architect Samuel Sloan at Bills and Union Street, asserted to be "the finest Italianate house in West Tennessee and among the most outstanding in the state." Two-story brick building with square cupola.
• Hudson-Wood-Fish House (1835), 322 South Washington Street. Federal with Greek Revival-style portico.
• St. James Episcopal Church (1869), West Lafayette Street.
• St. James Episcopal Chapel (1870), West McNeal Street.
• Ingram House, "The Columns" (1860), 303 West McNeal Street. Greek Revival, remodeled in 1909 to add Colonial Revival portico and other.
• Wright-Smith House (1867), West McNeal Street.
• Bills House, "The Pillars" (c.1831), 322 South Washington Street.
• Mark House "Wrens Nest" (c.1860), 308 Bills Street.