The first recorded information regarding roads was in 1831. At that time the township was divided into twelve districts each with its own supervisor. The budget for that year was $19.78. Between 1831 and 1912, the township had as many as 24 road districts. In 1912, the township trustees divided the township into four road districts and each district had its own superintendent. The township hired men to work on the roads for a wage of $0.40/per hour for a man who had a team of horses and $0.20/per hour for a man without horses. The man with horses was to use the extra wage to purchase feed for his team of horses.

In 1918, the township trustees divided the township into two road districts. District number one was from Sherman Road south to the township boundary line, and district number two was from Sherman Road north to the boundary line. Eventually, the township became one district with a single department sometime in the 1920's.

In 1953, the township had approximately 33 miles of road to maintain which required $11,772.43 for the maintenance. By 1960, the township road system had grown to approximately 51 miles. Today, the township contains nearly 79 miles of township road, twelve miles of County road, and ten miles of State road.

Since the 1950's, there have been six road superintendents. They include Harlow Whiting, Howard Bond, Robert Lamoreaux (1963-1970), Lawrence Roseum (1970-1986), John Lulas (1986-1987), and Charles Mascella (1987-2012).

The department operated out of a small building on SR 306 (Chillicothe Rd.) located behind the Baptist Church. The Chester Township Road Department has operated out of its own garage facility along Parkside Drive since 1943. The building originally consisted of a four-bay brick structure that was shared with the fire department. The facility of today is located at 8558 Parkside Drive and includes two garages, an office, a cold storage pole barn, and a salt storage dome.