The English settlers soon built a palisade and moat-like ditch to protect entrance to the 174-yard (159 m) wide neck from the shore area.

Dale named the new settlement Henricus in honor of Henry Frederick, Prince of Wales, the elder son and heir apparent of King James I.

In 1939 during the Great Depression, the Virginia State Police moved their offices from downtown Richmond to a seven-room farmhouse located on 65 acres (260,000 m2) of land 3½ miles west on route 60.

Prior to the American Revolutionary War, a thriving port town named Warwick was located at the northwestern confluence of Falling Creek and the James River.

In a 1709 diary entry William Byrd II, the wealthy planter who had purchased 344 acres (1.4 km2) of land in the area, noted that "the coaler found the coal mine very good and sufficient to furnish several generations".

Commercially mined beginning in the 1730s, the coal fueled the production of cannon at Westham (near the present Huguenot Memorial Bridge) during the American Revolutionary War.

The toll road ran between the coal mining area of Midlothian near the headwaters of Falling Creek and the James River port of Manchester.

To improve access to markets, in 1825, a group of mine owners, including Nicholas Mills, Beverley Randolph and Abraham S. Wooldridge, resolved to build a tramway.

[10] During the American Civil War (1861–1865), Drewry's Bluff became a key defensive point for Confederate forces to block the Union's vastly superior Navy from taking Richmond by way of the James River.

Chesterfield County shares borders with three independent cities and was long exposed to annexation suits from any of them under Virginia law.

A small commuter bus company held operating rights in the county, but the expanded city granted the franchise to a competitor.

Richmond annexed 23 square miles (60 km2) of the county, including fire stations, parks, and other infrastructure, such as water and sewer lines.

Residents of the annexed area were unhappy about this change, as Richmond Public Schools was already involved in a contentious racial desegregation lawsuit in the Federal courts because of its failure to integrate.

Many political leaders have long believed that Virginia's annexation laws have created a barrier to regional cooperation among localities.

[14] Unless new revenue sharing or other agreements are reached, the county is at risk to annexation suits by any of the smaller independent cities of Colonial Heights, Hopewell, and Petersburg which adjoin it.

County leaders believed the Chesterfield residents were committed to individual auto use for most local, commuter, and through transportation of people.

With the increases in population, traffic, and poor air quality, some residents have asked the county to fund commuter bus services.

Although the Virginia Department of Transportation (VDOT) built interstate, primary and secondary highways throughout the 20th century, they quickly filled with traffic as the population and use of autos increased.

Today the Powhite Parkway features a new highspeed toll system that allows smart-tag and e-z pass holders to travel through at speeds of 45–50 mph.

The roadway features the high-level Vietnam Veterans Memorial Bridge over the shipping channel of the James River downstream from the deep-water Port of Richmond, to allow ample clearance for ocean-going vessels.

[15] The Virginia Department of Transportation (VDOT) is planning two superstreets in Chesterfield County to address left turns at high traffic volume intersections.

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.

[30] In 2014, CCSO became the first county in Virginia to publicly state that it would not honor U.S. Immigration and Customs Enforcement detainer requests unless accompanied by a warrant.

[31] A CCSO deputy was one of 6 law enforcement officers in Virginia found to be a member of the Oath Keepers organization when a list was leaked in 2022.

The largest ancestry groups in Chesterfield County include African American (18%), English (14.5%), German (12.5%), Irish (11%), Italian (4%) and Scots-Irish (3%).

The Career and Technical Center allows high school students to attend vocational classes in various fields of interest.

[47] Brightpoint Community College, a two-year institution of higher learning, has two campuses in Chesterfield County; one in Chester and one in Midlothian.

[50] At that press conference, Richmond Mayor Levar Stoney announced the activation of the Central Virginia All Hazards Incident Management Team (CVAHIMT), of which Chesterfield County is a member.

The CVAHIMT "was established to support the needs of the Central Virginia Region for management of major incidents and planned events that require a public safety response.

Additionally, the EOC provided a call center for residents and employees with general questions about county operations and services throughout the COVID-19 response.