It served initially as a port on the Rappahannock River for shipping agricultural products, especially the tobacco commodity crop.

The Rosegill Estate was developed as a plantation by Ralph Wormeley beginning in 1649, with construction of its major buildings through the 17th century.

This and other plantations in the county were developed for the commodity crop of tobacco through the 18th century, which was highly dependent on the skilled labor of enslaved African Americans.

[5] Following the American Civil War and emancipation, numerous freedmen stayed in the rural area of Middlesex County, working on the land for pay or a share of crops.

An archaeological survey of the property included in the first phase of the planned development has revealed what appear to be parts of the Nimcock village.

[6] The developer intends to proceed with building houses over a portion of the artifacts, which will render excavation and study of them impossible.

During the American Civil War, Urbanna was planned as the point of landing for General George B. McClellan's 1862 Peninsula Campaign of 1862 to take Richmond.

McClellan shifted to use Fort Monroe as the starting point, almost doubling the distance by land that troops had to travel to the Confederate citadel.

Delays in reaching the gates of Richmond allowed the Confederates ample time to erect substantial defensive batteries, contributing to the Union failure in this campaign.

The Historic Middlesex County Courthouse was built in 1850–1874 by architects William R. Jones and John P. Hill.

To the east, almost to Stingray Point, the Village of Deltaville is situated on State Route 33 between the mouths of the Rappahannock and Piankatank rivers.