Colonial Contradictions Self Guided Walking Tour of Williamsburg

What's Included

Meeting and pickup

Itinerary

• 1
  Market Square

  Located along the iconic Duke of Gloucester Street, Market Square was once the vibrant center of commerce, conversation, and community. Today, it’s more than just a picturesque green—it's a starting point for exploring Williamsburg’s layered past. What you see may look like the 18th century, but there's more here than meets the eye.

  10 minutes • Admission ticket free
• 2
  Colonial Williamsburg Magazine

  This humble octagonal structure once held something far more explosive than gunpowder: tension. In colonial times, the Powder Magazine stored arms for the defense of the colony—but it also became a flashpoint in the growing struggle between Crown and colony.

  10 minutes • Admission ticket free
• Raleigh Tavern (Pass by)

  More than just a place to eat and drink, the Raleigh Tavern was a hub of political conversation, private deals, and public defiance. When the royal governor locked the doors of the Capitol, colonial legislators simply gathered here instead. Within these walls, words were exchanged that would echo far beyond Williamsburg—proof that even revolutions need a meeting place.

  Admission ticket free
• (Pass by)

  Step outside the bars of colonial justice. Williamsburg’s jail once held everyone from petty thieves to pirates. Though simple in form, this stark structure reminds us that beneath the ideals of liberty were real systems of power and punishment.

  Admission ticket free
• Peyton Randolph House (Pass by)

  Elegant and imposing, this grand home belonged to one of the most influential men of his time. But behind its refined façade lies a more complicated story, of politics, privilege, and the many lives lived here, both free and enslaved.

  Admission ticket free
• 3

  Just steps from the colonial core, Prince George Street blends the charm of the past with the pulse of the present. Lined with boutiques, cafés, and galleries, it’s a favorite spot for a leisurely walk, a coffee break, or a little window shopping.

  20 minutes • Admission ticket free
• 4

  The Brafferton is one of the oldest buildings in Williamsburg, and one of the most quietly complex. Built as an “Indian School” in the 1700s, its elegant brick exterior hides a layered and often overlooked chapter in colonial education and control. Though not open to the public, the building’s presence still prompts reflection.

  10 minutes • Admission ticket free
• 5
  Bruton Parish Episcopal Church

  In continuous use since 1715, Bruton Parish Church is more than just a colonial landmark, it’s a living place of worship. Step inside this beautifully preserved sanctuary to see where governors, revolutionaries, and everyday parishioners once gathered. With original pews and centuries of stories, it offers a quiet counterpoint to the bustling world outside.

  10 minutes • Admission ticket free

Additional info

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Suitable for all physical fitness levels
• Works entirely offline once downloaded—no cell service required
• GPS-triggered audio plays automatically based on your location
• Flexible - Buy once, use any day/time—access never expires

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