The communities in Montgomery County have notable and diverse architecture.

National Historic Register

Montgomery County boasts places listed on the National Historic Register including: Montgomery County Jail, Montgomery County Courthouse, Chautauqua Pavilion, The Firehouse Restaurant, Red Oak Library, The Osborne House and The Colonel Hebard House.

Montgomery County Courthouse

Montgomery County Courthouse was built in 1890 of red Missouri limestone. The interesting building of Richardsonian Romanesque design is listed on the National Historic Preservation Register and still has the historic interior intact.

Historic Heritage Hill Tour

Take a stroll or drive along Red Oak’s Historic Heritage Hill Tour and experience the community’s hallmark collection of turn of the century architecture. The tour embodies a wide range of architectural styles including excellent examples of Queen Anne, Georgian, Italianate, English Tudor, Colonial Revival, and Frank Lloyd Wright’s Prairie Style. The locations that are included on the Heritage Hill Tour were built from the 1870s through 1916.