Fort Monroe

In late August of 1619, an English ship carrying about twenty or more captive Africans, seized from a Portuguese slave ship, arrived at Point Comfort, where the captives were traded to the Virginia colonists for supplies. These are the first documented Africans brought to England's mainland American colonies, and their arrival marks a foundational and tragic moment in the history of slavery in what became the United States.

Those men and women, and the many who followed, were forced into a system of bondage that would grow over the next two and a half centuries into the vast institution of American slavery. Fort Monroe now bears the weight of remembering that beginning honestly, marking the very shore where it happened, so that the human beginning of a long injustice is neither hidden nor forgotten.

When the Civil War broke out in 1861, Fort Monroe stayed in Union hands even as Virginia seceded, an island of federal control deep in the Confederacy. That spring, three enslaved men, Frank Baker, Shepard Mallory, and James Townsend, escaped to the fort seeking freedom. The Union commander, General Benjamin Butler, refused to return them, arguing that as property being used against the Union they could be seized as contraband of war.

Word spread fast, and thousands of enslaved people made their way to the fort, which became known as Freedom's Fortress. Butler's contraband decision helped push the federal government toward emancipation and set a precedent that reverberated across the South. On the same ground where slavery in the colonies began in 1619, enslaved people in 1861 seized their own freedom and helped begin its end, one of the most extraordinary turns in American history.

The fort itself is an engineering marvel. Built in the decades after the War of 1812 to guard the vital harbor of Hampton Roads, it is the largest stone fort ever constructed in the United States, an immense stronghold of granite and brick surrounded by a water-filled moat. A young army engineer named Robert E. Lee helped oversee its construction in the early 1830s, long before the war that would divide the nation.

Because it never fell and was never abandoned, the fort grew into a full community over its long life, with officers' quarters, chapels, a lighthouse, and gracious homes lining its shaded streets inside the walls. After the Confederacy collapsed, its former president Jefferson Davis was imprisoned here for a time. The army finally left in 2011, and much of the site became a national monument, preserving both the fortress and the living town within it.

Old Point Comfort has drawn people to its breezes and views for centuries, once even as a seaside resort, and the waterfront remains one of the fort's pleasures. Visitors can walk the ramparts and moat, stroll the beach, and look out over the busy harbor of Hampton Roads, where warships, cargo vessels, and the daily life of one of the world's great ports pass by.

As a national monument, Fort Monroe now welcomes visitors to explore its layered story, from the 1619 landing to Freedom's Fortress to its long military career. The Casemate Museum inside the walls interprets that history, and the whole site invites a slow, thoughtful visit, a place where a beautiful shoreline and some of the heaviest history in the country meet in one spot.

The closest Boutel™ stays, so you can turn this stop into an overnight. Each is an independently owned, editorially selected place to stay.