Colonial Contradictions Self Guided Walking Tour of Williamsburg

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Colonial Contradictions Self Guided Walking Tour of Williamsburg

By Drives & Detours

Free cancellation available

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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, labour, 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 travellers, 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

1h
Opening hours: Thu 8:00 am-8:00 pm
English

Travellers

Languages available

Price details

NZ$17.34 x 1 AdultNZ$17.34

Total

What's included, what's not

Flexible Usage (unlimited access)
Audio Guide
App and Tour Download
Smartphone (bring your own)

Know before you book

Infants and small children can ride in a pram or stroller
Public transport 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

Located along the iconic Duke of Gloucester Street, Market Square was once the vibrant centre 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

This humble octagonal structure once held something far more explosive than gunpowder: tension. In colonial times, the Powder Magazine stored arms for the defence 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 storey, of politics, privilege, and the many lives lived here, both free and enslaved.

Prince George Street

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 favourite spot for a leisurely walk, a coffee break, or a little window shopping.

105 Jamestown Rd

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

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

Market Square
- 23185, Williamsburg, Virginia, United States

Meeting/Redemption Point

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

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