Flowerdew appears to have been occupied as early as the Late Pleistocene by Paleo-Indian hunter-gatherers and later, the Weyanoke (or Weanock) tribe as part of the powerful Tsenacommacah Chiefdom. Upon the end of the First Anglo-Powhatan War and the introduction of tobacco to the colony, George Yeardley founded the Flowerdew Hundred Plantation, which continued to operate as such until the early 20th c. in the hands of different owners. Africans lived and worked at the site, at first as indentured servants and later as slaves, producing a material record in the landscape. During the Revolutionary War, General Benedict Arnold left his mark at Flowerdew. Later, during the Civil War, General Ulysses S. Grant built a famous pontoon bridge, explored by archaeologists, across the James on the bank near Flowerdew. Thus, Flowerdew opens multiple windows into a frequently problematic past, constituting a cross-section of different chronological eras and interacting or clashing cultures.