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 1870's through 1916.
The tour begins at the Montgomery County Courthouse, built in 1890 of red Missouri limestone. This interesting building of Richardsonian Romanesque design is listed on the National Historic Preservation Register and still has the historic interior intact. Your tour ends at one of Red Oak's most outstanding attractions, the Chautauqua Pavilion located in Chautauqua Park. This pavilion, built in 1907, is the largest covered pavilion west of the Mississippi and is also listed on the National Historic Preservation Register.
Other places of interest include the Carnegie Library, the Murphy Calendar Company building and the Chicago, Burlington & Quincy Depot, which has been restored to its original 1903 charm, and houses a WWII Memorial Museum.
Places listed on the National Historic Register include: Montgomery County Jail, Montgomery County Courthouse, Chautauqua Pavilion, the Firehouse Restaurant, Red Oak Library, the Osborne House, and the Colonel Hebard House.
