By the late seventeenth century, the fresh soil of Dinwiddie began to draw planters from Tidewater and its overworked land. Dinwiddie's first settlers were mostly English and their African American slaves, but they also included a few Huguenots. In the first half of the eighteenth century, the region became even more desirable to planters when Petersburg and nearby

Richmond were established as inspection stations for tobacco before it could be exported. In 1752 the county of Dinwiddie was formed from Prince George County and named for Robert Dinwiddie, lieutenant governor of Virginia from 1751 to 1758. The town of Dinwiddie is now the county seat, but Petersburg, which became an independent city in 1850, was probably the site of the first court sessions. Many questions about the county's origins remain unanswered because most of its early records were destroyed during the Civil War.

The gentle hills and flatlands of Dinwiddie still grow tobacco, but small operations have closed and larger ones are adapting their practices to new tobacco-growing technologies and labor markets. Log barns are being replaced by metal bulk barns and less laborious farming methods are used. Raising livestock, the cultivation of soybeans, cotton, peanuts, wheat, and hay, and the harvesting and processing of forestry products are important components of Dinwiddie's economy. Except for the area near Petersburg, the county is still sparsely populated, and most of that along the railroad. Early residences, built when land was relatively cheap and expensive utility hook-ups unknown, were set much farther back from the roads than those in the colder Piedmont where the inconvenience of clearing snow and ice may have been factors that drew houses nearer the main roads.

Almost all of Dinwiddie's early structures are frame with stone or brick foundations and chimneys, and, before the middle of the nineteenth century, most of the more elaborate houses were only one-and-a-half stories. Early-twentieth-century sprawling one-story stores and filling stations, characteristic of Southside, still serve much of the county's needs. In the midst of traditional, almost hidebound, building practices, a surprising number of Postmodern buildings give fresh life to Dinwiddie County's architectural mix.