Williamsburg Self-Guided Historical Walking Tour

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.

Meeting Point

Haunted Williamsburg

102 W Duke of Gloucester St, Williamsburg, VA 23185, USA

The tour starts at Duke of Gloucester Street, between the courthouse and the Market House.

What's included:

• Flexible Usage (unlimited access)
• Audio Guide
• App and Tour Download

Not included:

• Smartphone (bring your own)

What to expect:

Duration: 1 hour

Market Square

Williamsburg, VA 23185, USA

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

Colonial Williamsburg Magazine

103 E Duke of Gloucester St, Williamsburg, 23185, Virginia

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

Raleigh Tavern

413 E Duke of Gloucester St, Williamsburg, VA 23185, USA

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.

Pass by without stopping

The Public Goal

461A E Nicholson St, Williamsburg, VA 23185, USA

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.

Pass by without stopping

Peyton Randolph House

100 W Nicholson St, Williamsburg, VA 23185, USA

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.

Pass by without stopping

Prince George Street

Prince George St, Williamsburg, VA 23185, USA

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

Brafferton

Brafferton, 105 Jamestown Rd, Williamsburg, VA 23185, USA

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

Bruton Parish Episcopal Church

201 W Duke of Gloucester St, (Next to Palace Green), Williamsburg, 23185-4201, Virginia

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