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Colonial Contradictions Self Guided Walking Tour of Williamsburg

By Drives & Detours
Free cancellation available
Price is $10 per adult
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Features
  • Free cancellation available
  • 1h
  • Mobile voucher
  • Instant confirmation
  • Multiple languages
Overview

Step into the heart of Colonial Williamsburg on this self-guided walking tour that goes beyond the costumes and reenactments. This tour invites you to explore not just what happened, but how it's remembered. Along the way, you'll uncover stories of power, protest, labor, and legacy.

Each stop reveals how colonial life was lived, contested, and reimagined. As you walk, you'll hear about the celebrated and the overlooked: from revolutionaries and craftsmen to the enslaved and the displaced. Rather than simply retelling history, this tour asks deeper questions about memory, identity, and what it means to inherit the past.

Designed to be thoughtful and accessible, this tour is perfect for curious travelers, history buffs, and anyone who wants to see Williamsburg in a new light.

Please note this tour is independently produced and is not affiliated with or endorsed by the Colonial Williamsburg Foundation and does not include admission to any ticketed exhibits.

Activity location

  • Market Square
    • 23185, Williamsburg, Virginia, United States

Meeting/Redemption Point

  • Haunted Williamsburg
    • 102 West Duke of Gloucester Street
    • 23185, Williamsburg, Virginia, United States

Check availability

Colonial Contradictions Self Guided Walking Tour of Williamsburg in Multilingual
  • Activity duration is 1 hour1h
    1h
  • Opening hours: Fri 8:00am-8:00pm
  • English
Price details
$9.99 x 1 Adult$9.99
Total
Price is $9.99

What's included, what's not

  • What's includedWhat's included
    Flexible Usage (unlimited access)
  • What's includedWhat's included
    Audio Guide
  • What's includedWhat's included
    App and Tour Download
  • What's excludedWhat's excluded
    Smartphone (bring your own)

Know before you book

  • 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
  • Children 10 and under are free

Activity itinerary

Market Square
  • 10m
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.
Colonial Williamsburg Magazine
  • 10m
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.
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.
The Public Goal (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.
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.
Prince George Street
  • 20m
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.
105 Jamestown Rd
  • 10m
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.
Bruton Parish Episcopal Church
  • 10m
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.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIES
    Market Square
    • 23185, Williamsburg, Virginia, United States

Meeting/Redemption Point

  • PEOPLEPEOPLE
    Haunted Williamsburg
    • 102 West Duke of Gloucester Street
    • 23185, Williamsburg, Virginia, United States

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