Step Back in Time: The Charles City County Historic Homes & Gardens Tour
Charles City County is one of Virginia’s most historic landscapes, nestled between Richmond and Williamsburg along Route 5, a National Scenic Byway. This stretch of road was once part of an ancient Algonquin Trail and later became one of the earliest English thoroughfares in the colony, carrying goods and correspondence between settlements. While the James River was the lifeline for trade and travel, Route 5 remains a living link to the past — and today it also parallels the Virginia Capital Trail, where thousands of cyclists ride between Jamestown and Richmond, taking in the scenic countryside.
Established as one of the four great corporations of the Virginia Company in 1618, Charles City became one of the eight original shires of the Virginia Colony in 1634. With centuries of history layered into its landscape, it is a rare opportunity to explore some of America’s finest examples of early architecture, from grand plantations to intimate family homes and historic churches.
This year’s Historic Homes & Gardens Tour invites visitors inside private homes, plantations, and churches across the county — living museums that tell the story of Virginia’s Indigenous peoples, the earliest English colonists, enslaved Africans, and generations of families who called Charles City home.
Highlights on the Tour
Shirley Plantation (1723)
Virginia’s first plantation, founded in 1613, and the oldest family-owned business in North America. The Great House, begun in 1723 as a wedding gift, still stands in its original form, surrounded by gardens, sweeping river views, and historic outbuildings.
House at Herring Creek (c.1880, rebuilt 2025)
A faithful recreation of the original Neston house, now a wedding venue with restored detail, a new barn, and space for celebrations — a nod to the past with an eye to the future.
Burlington (1818)
This classic farmstead west of Williamsburg offers history and modern hospitality. Features include a restored icehouse turned tap house, gardens, vineyards, and a newly built Bridal Cottage.
Milton (c.1625)
Overlooking the James River, Milton was once the summer home of Dr. Lyon Gardiner Tyler, president of William & Mary. Owned and restored by Harrison Tyler, grandson of President John Tyler, Milton represents nearly four centuries of Virginia history.
Laurel Bluff (c.1600)
Named for its brilliant mountain laurel blooms each May, this beautifully restored home sits high above the James River with walking trails, gardens, and inviting spaces perfect for outdoor living.
Westover Episcopal Church (1730)
Founded in 1613 and rebuilt in brick around 1730, Westover Parish has witnessed centuries of Virginia’s history — from Bacon’s Rebellion to the Civil War. Presidents and planters alike worshipped here, and today the congregation remains active in service and outreach.
Honoring the Land and Its People
As visitors walk these grounds, we also pause to remember the Indigenous nations — including the Powhatan, Chickahominy, and Monocan — who were displaced from this land, as well as the enslaved Native Americans and Africans whose forced labor built much of what still stands today. Their lives and contributions are central to the story of Charles City, and may we honor them as we seek justice and peace.
The Hidden Gem Beyond the Historic Triangle
Most visitors who come to the Historic Triangle focus their time on Williamsburg, Jamestown, and Yorktown — and for good reason. Together, these three sites tell the story of America’s beginnings, from the first permanent English settlement to the Revolutionary War battlefield where independence was won.
But here’s the secret: just a few miles up Route 5 lies Charles City County, a treasure trove of history and natural beauty that many travelers overlook. While tour buses line up in Colonial Williamsburg and families crowd into Jamestown Settlement, Charles City’s plantation homes, quiet country roads, and river views remain blissfully uncrowded.
What makes Charles City so special is its authenticity. You won’t find re-creations or costumed interpreters here — instead, you’ll step inside real plantation houses, historic churches, and private homes that have stood for centuries. You’ll hear stories of presidents, planters, enslaved laborers, and Indigenous peoples, all woven into the land that shaped them. Add to that the modern touches — like restored wedding venues, active vineyards, and riverside gardens — and you’ve got a county that feels both timeless and alive.
For those willing to venture beyond the well-worn path, Charles City offers a chance to experience Virginia’s history in a quieter, more personal way. It’s where the past feels close enough to touch, yet the present welcomes you with open doors.
Make It a Day on the Capital Trail
If you’re making the trip for the tour, why not pair it with a ride or drive along the Virginia Capital Trail? This 52-mile paved trail connects Richmond and Jamestown, passing right by Charles City’s plantations, historic churches, and scenic byways.
Here are a few must-stop favorites along the route:
🍽🍺 Indian Fields Tavern & 5 Fields Brewing – A stylish farmhouse restaurant paired with its own craft brewery right on Route 5. Perfect for a stop whether you’re riding or driving.
🍷 Upper Shirley Vineyards – Overlooking the James River, it’s one of the most scenic wineries in Virginia and a perfect stop for wine and small plates.
🍔 Culs Courthouse Grill (Charles City) – A local institution serving hearty meals and Southern hospitality, just steps off the trail.
🚲 Cap 2 Cap Cottage – My short-term rental just steps off the trail near mile marker 19.5, perfect for cyclists looking to spend a night or two exploring plantations, breweries, and history along the James.
Plan Your Visit
The Charles City County Historic Homes & Gardens Tour is a chance to step inside private properties rarely open to the public. It’s not just a tour — it’s a journey through the stories, architecture, and landscapes that shaped Virginia and America.
A tour of historic plantations, contemporary houses and gardens in the cradle of the nation
SATURDAY, SEPTEMBER 27, 2025 | 9:30 A.M. – 4 P.M.
📍 Location: Charles City County, Virginia
🎟️ For tickets and more information, visit: Click here
About John Womeldorf – Mr. Williamsburg
I’m John Womeldorf, a Realtor with Liz Moore & Associates, but most people know me as Mr. Williamsburg. For over 20 years, I’ve been helping people discover not just a house, but a community and a lifestyle in Greater Williamsburg, Richmond, and Hampton Roads.
I like to say I’m more of a local ambassador than a traditional agent. I answer questions about neighborhoods, schools, festivals, breweries, cycling trails, and even the best barbecue spots — because buying a home is about so much more than four walls and a roof.
My clients range from first-time buyers and military families to retirees searching for their forever home, and families relocating from across the country. What they all get is a personal guide who knows this region inside and out — someone who pairs deep local knowledge with creative marketing and a storytelling approach that helps homes stand out in a crowded market.
Through MrWilliamsburg.com, I write these posts as a way to share the stories behind our neighborhoods, highlight local life, and give future residents a real feel for what it’s like to live here. Whether I’m introducing you to a hidden gem of a community, breaking down the latest market trends, or spotlighting a favorite trail or tavern, my goal is always the same: to help you connect with this place I proudly call home.
And full disclosure — I might be in Europe right now (probably cycling along the Danube or exploring a music festival), but I’m always connected. I work wherever I am, and my clients know they can reach me no matter what time zone I’m in.
👉 If you’re thinking about buying or selling in Virginia — or even just daydreaming about a move — I’d love to connect. Call or text me at 757-254-8136 or email John@MrWilliamsburg.com.