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Colonial Williamsburg (Photo Courtesy Virginia Tourism Corporation)

Take a revolutionary road trip to Southeastern Virginia this summer

Did you know America’s founding and historical roots are less than a three-hour drive from the District? The short drive will take you where the Historic Triangle of Williamsburg, Yorktown and Jamestown engage with newly minted revolutions in cultural, gastronomic and outdoor experiences.

Here are some must visit spots in the historic towns:


Cycling your thing? Tour Virginia’s Capital Trail – 52 miles of paved pathway (pedestrians also welcome) extending from Richmond all the way to Jamestown along the heavily tree-lined Scenic Route 5 corridor. More than 400 years of history unfold along this meandering trail - one of the most stellar inland routes in North America. As you come into Charles City County traversing the James River, keep watch for Bald Eagles, the 4500-acre wildlife refuge here along the lower James is one of the country’s premier nesting areas and sightings are numerous.

Turn-key cycling experiences await riders with bikes, guides, and snacks at Basket & Bike, crafters of custom excursions and picnic rides. Their signature 14-mile ride begins and ends at Upper Shirley Vineyards where a wine tasting is included. For those preferring a livelier ride, horseback vineyard tours can be arranged through the winery.

Afterwards, enjoy a farm-to-table lunch and Upper Shirley’s award-winning wines on their massive deck. Try their Tannat, made from a lesser known Basque red grape. It’s soft and round with a hint of chocolate – unusual and impressive.

Experience first-hand the luxe-life of the landed-gentry Virginia colonists at three area James River Plantations.

Shirley Plantation, Virginia’s first, is America’s oldest farm and family-owned business, operated to this day by direct descendants of the 1613 builders. An architectural gem, the home and grounds (more than 800 acres) are open for touring year-round. Nearby Berkley Plantation wows as the Georgian Manse built by Benjamin Harrison IV in 1726 has 10 acres of terraced gardens and boasts hosting nine American presidents including George Washington. Tours of the Westover Plantation home are available only by appointment though the formal gardens are always accessible. Established circa 1730 by the founder of Richmond, William Byrd II, Westover sports an elaborate front doorway on the Georgian design that is said to one of the most copied in America.

Colonial Williamsburg maintains its place in America as the “world’s largest living history museum” with 500 buildings spanning over hundreds of acres. Wander Duke of Gloucester Street among the restored homes, shops and historic sites filled with period-reenactors who love to share the stories of this former capital of Virginia. The Governor’s Palace is always a highlight with the formal garden and boxwood-hedge maze a fun diversion.

For a more contemporary take on Williamsburg’s history – check out their newly established Taste Studio. The by-appointment experience demonstration kitchen showcases the food overarching all of Colonial Williamsburg’s dining options. Executive Chef Travis Brust shares insights into the colonial palate and creates mid-Atlantic southern cuisine inspired by the British spice trade. Demonstrations are fun, interactive and above all – tasty.

Historic Jamestowne allows for exploring the ongoing archaeological rediscovery project uncovering the remains of the original James Fort, church and out buildings. Stand on the spot where Pocahontas married John Rolfe and talk directly with onsite preservationists. History is not sugar-coated at the onsite “Archaearium” Museum that houses more than 2000 artifacts and tells evidence and fact-based tales they reveal – including those of gruesome survival cannibalism.

History is fun is the mantra at the Jamestown Settlement where Powhatan Indians, Europeans and Africans converged in 17th-century Virginia. This is the site of America’s first permanent English colony and history-buffs will geek-out at the quality and expansiveness at the exhibitions, artifacts and recreations on display here.

The newly christened American Revolution Museum at Yorktown uses the latest technological-wizardry to deliver a historical experience rivaling any other. Employing 4D-immersive theater (180-degree surround-sound, smell and motion), interactive displays and an actual recreation of a Continental Army encampment, historians here tell the story of America’s founding from its beginnings through the drafting of the Constitution.

Dining and Libations

The Williamsburg Tasting Trail showcases award-winning wineries, distilleries, breweries and even ancient mead-making.

Alewerks Brewing Company produces some of the best brew in the region. Try their Tavern Brown Ale, it’s complex yet mellow and brewed with six malt varieties. Silver Hand Meadery brews up one of the oldest known fermented drinks on earth – mead. Tastings here provide the backstory behind how an alchemy using honey, water and yeast is turned into a most elegant fermented beverage. Spirits – Whiskey and Gin – are handcrafted with love at Copper Fox Distillery. Situated upon the grounds of a former 1950s-era motor lodge, the “Fox” is cooking up some special small batch spirits. Williamsburg Winery’s well deserved accolades come from producing some of the finest wines not just in the state but the country. Try the Adagio – if there is any to be found- this fabulous Old-World-style red is a mélange of varietals including Petit Verdot, Cabernet Franc and Merlot.

The winery’s Café Provencal prepares beautiful plates highlighting local vegetables, proteins and dairy. A recent tasting menu featured a Heritage Rooster filled Ramp Crepe in a Green Curry – Dynamite.

Williamsburg’s Fat Canary is a family-affair with Chef Thomas Power, his parents and siblings all contributing to this culinary institution. While their adjacent cheese shop offers more than 200 varieties for sale, the main show is in the dining room where inspired plates like Mozzarella with Virginia Ham, Basil Pesto and Heirloom Tomatoes shine.


Williamsburg Inn has earned a well-deserved place in the National Register of Historic Places. Queen Elizabeth stayed here on two royal visits – In 1957 and 2007. The Inn is a luxurious retreat with all-suite accommodations, fine dining and an attentive staff. Our favorite guilty-pleasure is their over-the top breakfast with fresh green juice, Crab Hash-Benedict and Churro Waffles. Divine.