A Weekend in Williamsburg

The historic district is just the beginning in this gorgeous Virginia town. 


Julia Rutland
photographs by
Peter Frank Edwards

Williamsburg inn

Most first-time visitors to Williamsburg expect to see men tipping their tricorn hats to women in calico dresses and petticoats. And if you venture close to the historic district, that could definitely happen. But the Greater Williamsburg area offers much more than the past coming to life. Lush surrounding forestland, beautiful parks, and proximity to the James River make this area an open invitation to go hiking, biking, and boating. As for Williamsburg’s culinary offerings, you’ll find authentic dishes from 18th-century kitchens on the menus as well as high-end, modern interpretations with an emphasis on local sourcing and seasonality. There’s also no shortage of tempting retail here, along with wineries and other attractions to round out your weekend.

The Sideshow display

Discover “genre- busting” art at The Sideshow.

Man standing in front of the fence wearing period clothing

See the living-history museum that is Colonial Williamsburg.

Man driving a carriage

Take a carriage ride. 

Tins of peanuts

Bring home tins of delicious Virginia peanuts.

Start in the Historic District

Built in 1937, the Williamsburg Inn is part of Colonial Williamsburg Resorts, a group of authentically renovated properties that includes lodges and 18th-century Colonial Houses. While the inn’s 62 rooms are luxurious enough to tempt you to stay put, three golf courses—The Gold Course, The Green Course, and Spotswood Course—demand to be played. After an invigorating round, stop by The Social Terrace for their signature flatbreads or scone shortcake. Enjoy a mix of old and new pampering at The Spa of Colonial Williamsburg, where the offerings include a 17th Century Detoxifying Herbal Wrap.

Just across the road from the inn is Colonial Williamsburg. With more than 500 original and reconstructed period buildings, this 300-acre interactive living-history museum shows visitors what life was like in 18th-century colonial America. While you can meander around the historic district free of charge, demonstrations and certain buildings require a ticketed pass. Craftsmen’s workshops depict trades of the era. And the marching Fife and Drum Corps is guaranteed to stir your inner Yankee-Doodle, so check the schedule at the visitors center or

Shop Local

Conceived in 1927 during the restoration of Colonial Williamsburg, Merchants Square was one of the first planned shopping districts in the United States. Come here for the Williamsburg Farmers Market on Saturdays and the enormously popular 2nd Sundays Williamsburg Art & Music Festival, held 10 months of the year.

Hidden but worth a search is Blink, a second-story retail space that has been around for more than 40 years and sells everything from vintage-style furniture to clothing and jewelry. Branching out to Greater Williamsburg, explore the consignment furniture and decor at The Velvet Shoestring. Don’t miss The Sideshow gallery downtown or A Touch of Earth at The Gallery Shops, located to the north on Richmond Road.

Take home edible souvenirs from The Peanut Shop of Williamsburg in Merchants Square or the 5-Pack “Wittle” Tins from Whitley’s Peanut Factory.

Cheese Shop

 Get your picnic staples at The Cheese Shop. 


Try the Smoked Hanger Steak at the Amber Ox, where the menu changes to incorporate seasonal ingredients. 

Man driving a carriage

The Virginia Beer Company is as popular for its philanthropy as for its brews. 

Williamsburg Winery

The Williamsburg Winery is one of over 250 in Virginia.

Billsburg Brewery

You can’t beat the view at Billsburg Brewery. 

Cheese Plate

Enjoy a cheese plate at the upscale but chill Fat Canary.

Eat & Drink

Stop by Aromas World coffeehouse for a breakfast of poached eggs over grits or the handheld breakfast burrito. Another great hangout is The Cheese Shop. Try a made-to-order sandwich, or shop for picnic fare in the cold cases. The Amber Ox menu changes seasonally, but evergreen favorites include The “AO” Burger with pimiento cheese and caramelized-onion jam.

Enjoy a hearty grilled meatloaf sandwich at Blue Talon Bistro, followed by a decidedly adult dessert beverage like the “Copper Foxy” Milkshake with whiskey. Upscale but not fussy, the Fat Canary offers incredible, exquisitely plated dishes. The thick, juicy heritage-breed pork chop is a favorite at Cochon on 2nd, while the classic American menu at Food for Thought offers a wide variety of meats raised with no added hormones or antibiotics.

A good meal deserves good wine. Thanks to years of dedication and grafting science, Virginia is now one of the top producers in America, with 250-plus wineries. Save time for the Williamsburg Tasting Trail, which includes wineries, microbreweries, and distilleries. The Williamsburg Winery at Wessex Hundred, with its bright tasting room, is the only winery in Greater Williamsburg.

For a brew with a view, order a pint of James City Export Lager or another draft at Billsburg Brewery as you watch the sunset over the Jamestown Yacht Basin. The Virginia Beer Company’s motto of “Beer, People, Purpose” reflects its community engagement and philanthropy. Recent releases include a Mosaic India Pale Ale in honor of the Keep Virginia Beautiful campaign. Check their online calendar of food trucks visiting the beer garden, along with specials and events.

What was once a sprawling hotel on Capitol Landing Road now serves as an innovative production facility for Copper Fox Distillery. Try their recent entry, the Peachwood American Single Malt.


Connecting Virginia’s Historic Triangle—Jamestown, Williamsburg, and Yorktown—is the Colonial Parkway. The 23-mile road, paved using river gravel, is considered one of the prettiest scenic drives for travelers.

At Jamestown Beach Event Park, which is perched on the James River, settle into one of the picnic pavilions and paddle, swim, or sunbathe the day away. Spend the afternoon, and take advantage of the off-leash dog park, charcoal grills, and kayak rentals.

On nearby Jamestown Island, step onto the site of Historic Jamestowne, where men from England’s Virginia Company landed in 1607. Stop by the visitors center for exhibits that document how three cultures—European, African, and Powhatan Indian—intertwined in the early days of America’s founding. The Jamestown Settlement combines a gallery of exhibits with an outdoor living-history museum. Visit Jamestown Glasshouse, where glassblowing is done much as it was over 400 years ago.


Dig into history at the American Revolution Museum at Yorktown, where George Washington led the Continental Army to victory in the last major battle for independence from Britain. Now, the picturesque town includes a public dock, shopping village, local restaurants, and pristine Yorktown Beach, which sits along the banks of the York River and includes ADA-compliant walkways for universal access. Docked at Riverwalk Landing Piers, the schooner Alliance offers sightseeing trips down the York. Book a guided Segway excursion at Patriot Tours & Provisions to see the waterfront, and then grab a bite at the Yorktown Pub.

Schooner in the bay

Book a sail on the schooner Alliance on the York River.

Kayak Jamestown Beach

Kayak Jamestown Beach on the James River, where an event park has an off-leash green space for dogs.

Get Outside

The seven planned trails that make up Great City Walks, varying from paved paths to challenging woodland treks, will take you past historic sites. Look for information at visitors centers or

Farther afield is Freedom Park, a 600-acre forest with 2 miles of multiuse trails and 20 miles of mountain bike routes, one of the first free black settlements in America, the Williamsburg Botanical Garden, and two Go Ape treetop courses.

The Historic Jamestowne Bike Trail on Island Loop Drive offers a choice of 3- or 5-mile loops, which you can complete by car if you’d like.

Boating provides yet another way to experience this area’s scenic beauty. The James River is Virginia’s largest, running across the entire state from the Appalachian Mountains to the Chesapeake Bay. Canoe and kayak rentals are available at James City County Marina, convenient to the Jamestown Settlement and Historic Jamestowne.

The river supports a notable comeback of the bald eagle, hosting the largest roosting area on the East Coast. As you paddle this venerable channel, keep your binoculars handy to catch sight of our glorious national bird. And if you feel compelled to salute, so be it.

Start planning your own trip to Greater Williamsburg here.