Every historic building in Virginia has a story contained within its walls. From small residential homes to great churches and castles, hidden narratives can always be found — if you know where to look. Here are the intriguing stories behind some of the oldest buildings in the Commonwealth.
Jamestown Church
Constructed in 1639, Jamestown Church is the oldest building in Virginia — and one of the oldest structures in the entire United States. Although much of the modern church was in fact constructed in 1906, the 1639 church tower and foundations still remain. Amazingly, the church had already been rebuilt three times by 1639, with the original construction thought to have taken place in 1607 under the oversight of Captain John Smith. The first Jamestown Church burned to the ground in less than a year, and the second fell into a state of disrepair not long after. Undeterred, colonists constructed a third church in 1617, which thankfully avoided the fate of its two predecessors and was used until 1639 when the colony expanded to the point that a new structure needed to be built. The fourth version was never finished and in 1676 it suffered the same unlucky fate as the first when parts of it burned during Bacon’s Rebellion. The foundations and tower of the 1639 version survived until modern day, however, thanks in part to the efforts of Preservation Virginia. Today, the aforementioned tower is the last above-ground structure from when Jamestown was still the capital.
Broad Bay Manor — Virginia Beach
A building so old it’s unclear exactly when it was constructed, Broad Bay Manor is thought to have been built sometime between 1640 to 1660 by a colonist named Thomas Allen. A tapestry of history from many eras, only the middle of the house is thought to be from the 17th century. The right addition is thought to have been constructed during the 1770s, and the left side is an even more modern addition from the 1980s. Due to its diverse background, the history of Broad Bay Manor comprises more than just the colonial era. Accounts indicate that the part of the house burned down from a lightning strike during the 1920s and was the site of large parties during the prohibition era. Today, the historic building remains a residential home.
Bacon’s Castle — Surry County
Built in 1665 by colonist Arthur Allen, Bacon’s Castle is the oldest documented brick building in both Virginia and the larger United States. Originally considered to be just a house, the building became known as “Bacon’s Castle†during Bacon’s Rebellion in 1676 when the followers of Nathaniel Bacon occupied it as a defensive outpost. Although Nathaniel Bacon himself never lived at Bacon’s Castle, his legacy remains tied to the location. Today, Bacon’s Castle is maintained by Preservation Virginia as a historic museum and a living monument to a key chapter in Virginia history.
Willowdale — Painter
First constructed in 1666 by a farmer named John Smith (unrelated to the historic figure), Willowdale has been owned by the same family for an astonishing 352 years. Located in a small town of 200 called Painter in Accomack County, the family home is thought to be the oldest building on the entire Eastern Shore. Although only a few small parts of the original house are thought to remain, the building is nonetheless historically significant as one of the only standing examples of a building from its era.
Toddsbury — Gloucester County
Built around 1669 by a colonist named Thomas Todd, the history of Toddsbury remains something of a mystery. For one, it is unclear exactly which Thomas Todd built the house. Records show one colonist Thomas Todd alluded to the Toddsbury property in his will, however he gave the land to his son (also named Thomas Todd), and it is unclear whether the father or the son was the true builder of the Toddsbury building. In any case, records indicate the Todd’s continued to live at Toddsbury until 1880, where it was sold to a different family. Today, the house continues to be a private residence.
Preservation Virginia is a private, non-profit organization and statewide historic preservation leader founded in 1889 that is dedicated to preserving, promoting, and serving as an advocate for Virginia’s cultural and architectural history.