Bermuda Hundred occupies a strategically important peninsula where the Appomattox River meets the James. Long before English settlement, this was part of the homeland of the Appamatuck, an Algonquian-speaking people within the Powhatan chiefdom. Their village and fields made use of fertile river terraces and a transportation network centered on waterways. The later English town was planted close to this established Indigenous landscape, not on an empty frontier, and colonial expansion displaced the community that had shaped the place.

In 1613 Deputy Governor Sir Thomas Dale established Bermuda Hundred during an aggressive phase of Virginia's expansion beyond Jamestown. The name recalled both the Bermuda Islands and the English "hundred," a jurisdiction expected to support a defined group of settlers. Dale promoted fortified settlements, compulsory labor, and private cultivation. Bermuda Hundred became one of the colony's earliest incorporated towns, while nearby Henricus and other plantations extended English control along the James and Appomattox corridors.

Its riverside location made the settlement useful as a port and commercial landing. During the eighteenth century it served as an official port of entry with customs officers and tobacco inspectors. Vessels moving between inland plantations and the Chesapeake could collect produce, clear cargoes, and obtain information here. Roads toward Petersburg and Richmond met the river system nearby, so the community linked the plantation economy of central Virginia with Atlantic trade and imperial administration.

The Revolutionary War brought that transportation role into military focus. In January 1781 Benedict Arnold, now a British brigadier general, led a naval-borne force up the James to raid Richmond and destroy military stores. Bermuda Hundred briefly served as a British headquarters and anchorage during the Virginia campaign. Its position allowed troops and vessels to shift between the James, the Appomattox, Petersburg, and the Chesapeake while Virginia militia struggled to anticipate widely separated landings and raids.

Later in 1781 British forces under William Phillips and Arnold again used the James-Appomattox corridor before fighting at Petersburg. The war demonstrated why Bermuda Hundred had mattered for generations: whoever controlled its approaches could influence two navigable rivers and the communities they served. The same geography made the peninsula important during the Civil War, when the Union Army of the James established its base there in 1864 and became contained by Confederate defenses known as the Howlett Line.

The marker stands south of the historic settlement and compresses more than two centuries into a roadside account. Little remains of the busy colonial port, but the landscape still explains its repeated importance. Remembering Bermuda Hundred requires holding together Appamatuck occupation, English colonization, commerce dependent on enslaved labor, Revolutionary raiding, and Civil War campaigning. The site is therefore less a single battlefield than a long-lived river crossroads whose strategic value repeatedly drew governments, merchants, soldiers, and displaced communities.