The history of Chester Heights predates grants of William Penn, when the Swedes had penetrated some distance inland from the Delaware River and had found the rich soil very conducive to productive farming. To a remarkable extent, the area had continued to be so used until the last decade. In the 18th and 19th centuries, the borough was part of Aston Township, though this northernmost section of Aston did not have a village aspect as such. With the advent of a railroad, which made its first run-through on Christmas Day 1833, a concentration of houses developed. With the reach of the automobile, a settlement of homes sprang up along the oldest road in the borough. That route, now Valleybrook Road, was once known as the "Logtown Road" and was one of the earliest routes from Chester settlement to the interior. It wanders over and along the West Branch of Chester Creek and is noted for its abrupt curves at the borough's southern end.