Chesterfield County is largely bordered by two rivers which define miles of its boundaries. The major adjoining cities each originated at the head of navigation of these river, called the fall line. There, the hillier and rockier Piedmont region falls to the sandy and mostly flat eastern coastal plain Tidewater region, a change which creates barriers for ships going upstream on the rivers. Chesterfield County includes areas of both regions.
Richmond and Manchester were formed at the fall line of the James River. Most of the northern portion of Chesterfield County is part of what is called Richmond's "South Side". As the James River flows east to Richmond and then turns almost due south below the fall line for about 8 miles (13 km) before turning east, Henrico County encompasses much of Richmond's West End, North Side, and East End areas.
Chesterfield County borders on the Appomattox River to the south. Much of the southern and eastern portions of the county are considered part of the Tri-Cities area, which includes Petersburg, located at the fall line.
Until just recently most of Chesterfield was still rural. Development has brought many fine planned developments to the county and it has some of the top rated public schools in the area. Midlothian has the majority of the planned developments in the county. Bon Air was a train stop and a place for some to "summer" in the 1800's. Chester has strived to maintain their "village" feel as they grow into the 21st century. There is space to still spread out in Chesterfield.