Illustration by Clair Rossiter
Duke of Gloucester Street is the closest some will ever come to time travel. Williamsburg’s main drag starts off in Merchants Square, a charming shopping and restaurant district with an undercurrent of colonial history. As you make your way eastward, the tide shifts rapidly from present-day retail to rousing reenactments, where silversmiths and wheelwrights preserve centuries-old crafts. This is Disney World for history nerds, developed thanks to the vision (and financial support) of John D. Rockefeller in the 1920s. Today, the former colonial capital is a bustling and picturesque town that bridges tradition and modernity—and may inspire a newfound appreciation for oyster shell gravel and 18th-century furnishings.
FIT FOR A KING
Whether you’re a staunch patriot or have a loyalist streak, the Williamsburg Inn’s list of famous guests will put you in good company. Throughout its nearly century-long history, the inn has welcomed multiple U.S. presidents and Queen Elizabeth II. Stay in a room decorated with the perfect level of traditional formality, then hit the links at the Golden Horseshoe Golf Club or indulge in a spa day.
COLONIAL CURATION
If your interest in history is of the decorative and fine arts variety, stroll over to the Art Museums of Colonial Williamsburg, where you can brush up on American and British antiques dating back to the 1700s or learn more about both colonial and contemporary folk art.
A STEP BACK IN TIME
Williamsburg is perhaps best known for its abundance of tricorn hats and bonnets, which are a Colonial Williamsburg staple among the younger set. Explore the 301-acre living history museum to see firsthand how blacksmiths, carpenters, cooks, and gardeners worked in the 18th century and how they keep traditions alive today. The skilled workers throughout town spend time training in their chosen trades, serving as renowned experts for both visitors and other cultural institutions globally.
SAY CHEESE
The Power family opened the Cheese Shop in the 1970s, when artisanal cheese and good wine didn’t yet have the hold on society that it does today. Their forward-thinking shop took off, and today they’re known for a selection of hundreds of imported and domestic cheeses, charcuterie boards, more than 4,000 bottles of wine, and signature sandwiches. Try a country ham and Swiss with their famous house dressing for a true taste of Williamsburg.
SHOP THE SQUARE
Merchants Square brings together retailers inspired by history with those catering to modern style. Pick up Williamsburg brand home items at Brick & Vine, vibrant clothing at Three Cabanas, or classic menswear at R. Bryant, Ltd.
SING FOR SUPPER
Fat Canary, a bistro in the heart of Merchants Square holds just 15 tables where regulars dine on perfectly pan-seared duck breast and roasted chicken. Don’t worry if you forgot to snag a reservation—there’s a lively downstairs wine cellar serving the same dishes, plus a more casual menu (the Bolognese is a must order).
SCRIPTED HISTORY
Score tickets to a performance at the Kimball Theatre. First opened in 1933, this 400-seat venue’s lineup now includes Shakespeare, live music, and, fittingly, historic productions and readings, like Howard Ginsberg’s Jefferson & Adams.
This article appears in the Fall 2025 issue of Southbound.
