Many of the earliest structures in Courtland were built of logs, and were later replaced with frame and brick buildings.

Development plateaued by 1830, but received a slight bump from the Tuscumbia, Courtland and Decatur Railroad beginning in 1834.

The town saw a resurgence after the Civil War, with early construction including the Presbyterian church.

Most of the commercial area around the public square was rebuilt in brick in the 1880s through the 1900s, while many older houses were replaced with Victorian examples around the same time.

[2] The boundaries of the district were increased in 1998 to include buildings representing Courtland's working-class and post-World War II growth.