During the mid 19th century, citizens began to demand smoother roads. P.J. Burchell and O.M. Butler made plans for a turnpike or toll road west of St. Charles, and in the late 1840s, laid a new road. Unlike our roads today which are made of concrete or asphalt, this road consisted of wooden planks. The wood used for the toll road was cut from an area north of St. Charles. A crew of men completed construction of the road in 1850. Known as "Plank Road," it extended westward from the tollhouse and curved in the direction of what is Dean Street today. Toll gates stood at either end of the road.

Although the plan was to connect St. Charles with the neighboring community of Sycamore, Plank Road only extended for three miles west of the tollhouse. It was at this tollhouse where Edward Conner and Dr. Junkett collected tolls and oversaw the road. This building still stands today and serves as a residence.

Although this road was an improvement over the previous dirt road, travel remained bumpy. The plank road also proved to be difficult to maintain. After approximately seven years, the owners, Major P.J. Burchell and O.M. Butler, tore up the road. The planks served as fuel in Butler's paper mill and Burchell's hotel. After dismantling the planks, the roadway continued to serve as a turnpike.