The Ashland area was settled by Scots-Irish who came from Kentucky about 1820. An Indian trading post was established near the present intersection of Broadway and Main Streets. The Town was laid out in 1852 but was not incorporated until 1877. It was named Ashland after Henry Clay’s estate in Lexington, Kentucky. At the time of Ashland’s incorporation it was a well-established farming community on a toll road which ran from Columbia to Claysville, then an important river port.

The Trade Center was started about 1875 by William Bass and J.W. Johnston and it became the largest general store in Missouri. It had the first telephone in Missouri, outside of St. Louis. The line ran to a branch store in Guthrie, 8 miles east on a branch of the Chicago and Alton Railroad.

Bass and Johnson also ran the Ashland stock sales which shipped large herds of mules to the deep south. They established the Farmers Bank in 1881, build a grist mill (The Ashland Milling Co.) in 1877, and started a newspaper, called the "Ashland Bugle" in 1875. James L. Wilcox bought the Bugle in 1877 and published it single-handedly as a weekly paper for 63 years, establishing a national reputation for himself and his newspaper.

Before the turn of the century Ashland had a packing house, a cooperage, a cannery, 2 hotels, 3 grocery stores, several blacksmiths & livery stables, 7 physicians, several lawyers, a drug store, 2 opera houses, and a noted brass band. Ashland was the home of fine saddle horses. It had two race tracks and several training tracks just outside the city limits.