Colonial Contradictions in Williamsburg
Go beyond the costumes on this self-guided audio walking tour
What to Expect
Step into the heart of Colonial Williamsburg, where cobblestone streets, preserved buildings, and manicured greens give the illusion of stepping back in time. This self-guided walking tour invites you to explore the sights and the evolving meanings behind them. From Market Square to Bruton Parish Church, each stop connects to broader themes of memory, identity, and national transformation.
As you walk, the GPS-triggered audio brings to life the power struggles, personal stories, and symbolic weight embedded in the town’s layout. You’ll encounter voices too often left out of traditional narratives, including enslaved people, Indigenous students, artisans, and women
Rather than offering a reenactment, this tour encourages reflection: How do we choose to remember the past? Whose stories are celebrated, and whose are obscured? Whether you’re a history buff or a curious visitor, this walk through Colonial Williamsburg challenges you to see familiar landmarks 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. ⚠️
Ready to go? Book below or download our app and purchase directly from your phone.
📍 Location: Williamsburg, VA
🚶♂️ Type: Walking tour
⏱ Duration: Approx. 2 hours (flexible)
✅ Includes: App download, GPS-triggered audio, No expiration
📶 Works Offline: Download ahead of time - no cell service required
🎧 Multiple Languages: English, Spanish, French, German
⚠️ Important Info: Some exhibits require paid admission (not included)
Get Ready for Your Williamsburg Self-Guided Tour
Step into Colonial Williamsburg on a self-guided walking tour that looks past the period costumes and polished performances to reveal a deeper story.
Rather than focusing only on events, this experience explores how history has been shaped, interpreted, and remembered over time.
As you move through the historic streets, you’ll encounter stories of authority and resistance, daily labor and lasting legacy.
Each stop offers insight into how colonial society functioned—and who benefited, who resisted, and who was left out.
You’ll hear about well-known figures alongside the craftsmen, enslaved people, and displaced communities whose lives were equally woven into Williamsburg’s past.
This tour doesn’t just recount history—it invites reflection on memory, identity, and what it means to inherit a complicated past.
Thoughtful, engaging, and easy to follow, it’s ideal for curious explorers, dedicated history fans, and anyone looking to experience Williamsburg from a more nuanced perspective.
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.
What You’ll See on Your Williamsburg Walking Tour
Colonial Williamsburg’s Merchants Square
Stretching along Duke of Gloucester Street, this area once served as a lively center for trade, conversation, and civic life. While it may resemble the 18th century, Merchants Square is also a gateway to the many layers of interpretation that shape Williamsburg today.
Colonial Williamsburg Magazine
This small octagonal building once stored gunpowder for the colony’s defense. It also became a point of friction between colonial leaders and the Crown, highlighting the growing tensions that preceded the revolution.
Raleigh Tavern
Far more than a tavern, this was a gathering place for political debate and bold decision-making. When official meeting spaces were closed, colonial leaders convened here, proving that ideas—and revolutions—often take shape outside formal halls.
The Public Gaol
Williamsburg’s jail held a wide range of inmates, from minor offenders to notorious criminals. Its stark presence serves as a reminder that ideals of liberty existed alongside systems of control and punishment.
Peyton Randolph House
Once home to a prominent political figure, this elegant residence reflects wealth and influence—but also the complex realities of power, privilege, and enslavement that underpinned colonial society.
Prince George Street
Bordering the historic district, this street blends past and present with shops, cafés, and galleries. It’s a pleasant place to pause, stroll, and experience how Williamsburg continues to evolve beyond its colonial core.
105 Jamestown Road (The Brafferton)
One of Williamsburg’s oldest surviving structures, the Brafferton was built in the 18th century as an “Indian School.” Though closed to visitors, it stands as a quiet reminder of colonial education, cultural control, and overlooked histories.
Bruton Parish Episcopal Church
In continuous use since 1715, this church remains both a historic landmark and an active place of worship. Inside, original features and centuries of stories offer a reflective space once shared by governors, revolutionaries, and everyday residents alike.
Meeting Point
Your Colonial Williamsburg walking tour begins at Haunted Williamsburg on Duke of Gloucester Street, between the courthouse and the Market House.
FAQs About Our Williamsburg Walking Tour
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Entrance to Colonial Williamsburg costs the following:
Single-Day Ticket
Adult (13+): $37.50
Youth (6–12): $10.00
Multiday Ticket
Adult (13+): $55.00
Youth (6–12): $28.00
Free admission is available for active-duty military, reservists, National Guard personnel, retired military and veterans and up to three direct dependents on Memorial Day weekend or Veterans Day weekend. This is available once per year.
Active-duty United States military, reservists, National Guard personnel, retired military and veterans receive a 15% discount on single-day admission tickets for themselves and up to three direct dependents, with ID.
Teachers are eligible for a 25% discount on a single-day ticket, with ID.
Colonial Williamsburg also provides discounts through Museums for All, and other partnerships.
Visit the Colonial Williamsburg website for more information.
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A one-day skating ticket at the Liberty Ice Pavilion in Colonial Williamsburg costs the following:
Adult (13+): $18.00
Youth (3–12): $13.00
Skate Rental: $7.00
Visit the Colonial Williamsburg website for more information.
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Tours are fully refundable up to 24 hours in advance.
If it’s within 24 hours or you had an issue during your tour, email support@drivesanddetours.com. We review all requests individually and will always do our best to make things right.
Our goal is to ensure every traveler has a great experience exploring with Drives & Detours.
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Our Williamsburg walking tour covers approximately 2.5 miles (4 kilometers) and takes about 2 to 2.5 hours to complete at a leisurely pace. It follows public streets and outdoor walkways—comfortable shoes and weather-appropriate clothing are highly recommended.
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Yes, downloading the Drives & Detours app will give you full access to the tour you have purchased, as well as many other self-guided tours.
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Download the tour before you go. Some areas have poor signal, which can make downloading the tour difficult. Once the tour is downloaded, it will work without any cell signal
The tour audio plays automatically as you approach each stop
Want to see more? Tap “View Stop” to see photos and bonus content
To return to the map, tap the small down arrow between the “previous” and “next” buttons
Follow the blue line and audio directions to stay on route
Use audio controls to pause, rewind, or skip—just like a podcast
Safety first: Keep your eyes on the road or sidewalk, follow traffic laws, and stay aware of your surroundings
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No—download your Williamsburg tour before you go, and you won't need a cell signal. Drives & Detours’ tours work without any cell signal once they are downloaded to your device.
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Once you have purchased your Williamsburg walking tour from Drives & Detours, you can use it whenever you want. You can always take the tour another day if the weather is bad on the day you plan to take it.
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Unfortunately, Dives & Detours cannot guarantee that the Harpers Ferry self-guided tour is accessible. People with wheelchairs, strollers, or mobility impairments are very welcome, but we recommend checking the Colonial Williamsburg website for detailed information.
Pro Tips for Your Drives & Detours Williamsburg Self-Guided Tour
Download before you go.
Enable location services—GPS triggers the audio.
Use earbuds, headphones, or your car speakers.
Pause and resume anytime. If you take a break, just reopen the app and head back toward your last stop.
Lost your way? Tap any pin on the map, then tap the right-turn-arrow icon to open your default maps app for turn-by-turn directions to that spot.
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