Historic Williamsburg

9. Duke of Gloucester Street

Williamsburg, VA

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Franklin Delano Roosevelt once called Duke of Gloucester Street the "most historic avenue in all of America." It began as a narrow path used by the Indians, and was later expanded by the colonists to admit horses and carriages. Before Virginia's General Assembly officially recognized the locale we now know as Williamsburg, it was merely a small community of crude buildings called "Middle Plantation." In 1699 Williamsburg was established, and with it, the main thoroughfare was named for Prince William, Duke of Gloucester. It stretches from the College of William and Mary eastward, about a mile to the Capitol. The carriages of landed gentry shared this main road with laborers, livestock, and wagons. Beautiful homes, shops, and taverns all lined the bustling street. You will notice that most shop and restaurant signs feature painted pictures. This is because all businesses along the street were required to display picture signs, so that illiterate residents would know which goods and services were offered inside. The brick sidewalks that border Duke of Gloucester street today did not exist in colonial times. Bricks were expensive, and only wealthy people could afford to pave their walkways. Instead, the main road was dirt. To reach their destinations, pedestrians often had to brave huge clouds of dust on dry days, and a thick layer of mud on rainy days. Much of the funds for the street's upkeep and maintenance were swept away to Richmond when the Virginia Capitol was moved there. Duke of Gloucester street fell into disrepair and was completely altered over time. In the 20th century, concrete sidewalks, telephone poles, cars, and modern buildings started sprouting up. Not until the Rockefeller restoration in the 1930s was the street restored to its simple and picturesque colonial appearance.