Unplug and Reconnect: Take a Revolutionary Road Trip This Fall 

There’s something about autumn that makes it easier to slow down. The air is cooler, the light is softer, and every turn in the road feels like an invitation to linger. 

This fall, take a trip that doesn’t just slow you down, it takes you back in time. In Williamsburg, Virginia, lanterns light brick-lined streets, carriage wheels clatter past shopfronts, and costumed interpreters bring the 18th century to life.  

As Virginia builds toward the nation’s 250th anniversary in 2026, it’s the perfect time to experience where America’s story began. 

So, switch your phone to Do Not Disturb and take a step back in time. Here’s how to do a weekend in Williamsburg, Yorktown, and Jamestown—without rushing a moment.   

Day 1

Hit the road early to watch the sun light up the fall foliage. Queue up a history-inspired audiobook or podcast to set the mood.  

As you get close, trade the interstate for the scenic back roads. Route 5 winds past James River plantations and quiet stretches of countryside, a fitting prelude to the history ahead. 

Spend the afternoon in Colonial Williamsburg. Stroll Duke of Gloucester Street, stop for warm ginger cakes at Raleigh Tavern Bakery, and discover colorful art and artifacts at the Art Museums of Colonial Williamsburg. Wrap up your first day with dinner at King’s Arms Tavern, where the menu nods to 18th-century recipes (don’t worry, there’s mac and cheese for picky eaters). Then, join a candlelit ghost tour for something slightly spooky before bed. 

Day 2

Fuel up at Aromas Coffeehouse before making the short drive to Yorktown, where Revolutionary history comes to life along the York River. 

Begin at the American Revolution Museum at Yorktown, where immersive outdoor living-history areas tell the story of the nation’s founding. Then, explore the Yorktown Battlefield, where the last major battle of the Revolutionary War was fought. Bonus: If you’re visiting in early September, 1781 Yorktown Before the Siege (September 6-7), transforms the Historic Main Street into an occupied colonial port, complete with historical interpreters, military drills, and camp life demonstrations.  

In mid-October, Yorktown Day (October 19) marks the anniversary of the British surrender with a parade, wreath-laying, and traditional fife and drum performances. Free transportation via the Yorktown Trolley will take you to the city’s historic sites.    

Break for lunch at a waterfront seafood spot along Riverwalk Landing, just a few minutes from Yorktown Beach. Unwind on the shore, browse boutiques or, set sail on a schooner cruise along the York River.  

Catch the sunset over the water and enjoy the area’s fresh seafood (oysters are a regional specialty) at a local spot like Water Street Grille, before the short drive back to Williamsburg. 

Day 3

Start your last day with coffee and pastries from Eleva Coffee Lounge before the last leg of your adventure in Jamestown.  

In Historic Jamestowne, you can explore the remains of James Fort and learn about ongoing archaeological digs discovering more of America’s earliest chapter. In Jamestown Settlement, the living-history museum invites you to walk in the steps of settlers and board a life-size replica of a ship that carried English colonists to Virginia. You’ll also learn about the Powhatan people, the powerful Indigenous nation that called this land home long before English arrival. 

If you have time to spare before the long drive north, grab a bite at Spoke + Art Provisions Co. and take a short ride along the Virginia Capital Trail, even 30 minutes is enough to enjoy the scenery before hitting the highway north.  

More Time?

If your idea of “unplugging” leans more toward leisure than lantern-lit tours, then Williamsburg has you covered. Tee off at the Golden Horseshoe Golf Club, where fairways wind through centuries-old oaks just steps from the Historic Area. Or, slip into full relaxation mode at The Spa of Colonial Williamsburg, where treatments draw on colonial-inspired botanicals (ginger, lavender, and orange blossom) for a restorative nod to the past.  

Families and thrill-seekers alike might add a half-day at Busch Gardens Williamsburg, where world-class coasters, European-themed villages, and seasonal festivals offer a completely different (but equally memorable) way to cap off your trip. 

Whether you spend your days in the 18th century, on the greens, screaming down roller coasters at Busch Gardens, or wrapped in the scent of lavender at the spa, Williamsburg’s magic is in how it slows you down. By the time you head home, you’ll have forgotten what your phone sounds like and you won’t have missed a thing. 

 

This is a paid partnership between Visit Williamsburg and Philadelphia Magazine