Drive time from Dulles: 5.5 hours
Winston-Salem, North Carolina, was once the seat of R.J. Reynolds’ thriving tobacco industry — and even known as Camel City, after the then popular cigarettes. While the nation’s second-largest tobacco company is still headquartered in the North Carolina city, its tobacco factories are no longer downtown. As a result, the community had to be resourceful and forward-thinking to avoid being a decrepit industrial ghost town.

Nowadays, the Winston-Salem Historic Tobacco District is a hip and highly walkable place to hang out. Former tobacco buildings dating from 1890 to 1959 are spread out across 31 acres, including the unmissable 130-foot-tall R.J. Reynolds smokestack. The area has been reinvented as the Innovation Quarter where visitors can find fun and welcoming spaces, like Bailey Park, a 1.6-acre greenspace that hosts festivals, yoga, concerts, and picnickers. You can grab caffeine and a dressed-up biscuit at Krankies Coffee. Before or after dinner, beer lovers can start the Craft Draft Crawl at Incendiary Brewing, known for its IPAs, or at Foothills Brewing, which started in 2004. For dinner, Six Hundred Degrees has a live fire kitchen and offers a range of à la carte meats with vibrant sauces on the side.
The downtown area is decorated with bright murals (check out the self-guided-tour) and sculptures that celebrate the city’s history and diversity. The Arts District hosts Art Crush, an arts-focused block party, every third Friday of the month from April to December, and you can also gallery hop through the area on First Fridays year-round.
Anyone who loves ogling historic homes will enjoy strolling the city’s gorgeous West End neighborhood, and you can stay in one through Summit Street Inns. This walkable area also boasts several lauded restaurants, including Mozelle’s bistro (known for its Southern flair) and Bernardin’s, a fine-dining destination.

For a deeper dive into the area’s historical past, head to Old Salem Museum & Gardens which offers lovely historic homes, businesses, and gardens to wander through and to learn about the area’s past Black, Indigenous, and Moravian people who inhabited the area. The site also hosts the Museum of Early Southern Decorative Arts and many Moravian works.

Outside of town, escape to Reynolda, the 1917 summer home of Richard Joshua Reynolds and his wife Katharine (an avid gardener and first cousin once removed). The 170-acre historic estate includes formal gardens and a newly restored Victorian conservatory, along with wooded trails, now owned by nearby Wake Forest University. Inside the home, the art collection is being continually updated to represent Winston-Salem’s history more inclusively, including an exhibition called “Still I Rise: The Black Experience at Reynolda.” You might also enjoy works by artistic luminaries, such as John Singer Sargent and Georgia O’Keefe. Nearby Reynolda Village is an ideal place to pick up coffee and a truly delectable doughnut from Dough-Joe’s, if you need a recharge after all this exploring.
Feature image of Grant Park courtesy Visit Winston-Salem
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