Where to Play, Eat, and Stay in Winston-Salem, North Carolina

It turns out that Winston-Salem is its own kind of Art-o-mat: renovated after the era of tobacco-industry dominance and refocused on art and history. From the University of North Carolina School of the Arts to the Sawtooth School for Visual Arts, the town is saturated with creativity, artistic displays, and subsidized studio spaces. Winston-Salem is also full of great food, gorgeous green spaces, and a mellow vibe worthy of a visit.

Even getting there is a part of the fun, thanks to the relaxing Piedmont Triad International Airport (GSO) in Greensboro, which is about 30 minutes away, full of rocking chairs, and has affordable nonstop service to Chicago and other East Coast hubs.

Single Brother’s House. Photo: Quinn Kampschroer/Shutterstock

There’s a lot of history in Winston-Salem, and it’s on display throughout the city. I was dying to know how the city got two names, so let’s start there.

Winston-Salem’s name traces to the Moravians, members of a Christian religious group that still exists today. Moravians came from Europe to found Salem, North Carolina, in 1766. They created a thriving community (with the labor of enslaved people), and the town of Winston grew alongside them to provide goods and services that their religious beliefs wouldn’t allow. Eventually, Winston-Salem became one city with two names.

Old Salem is the place to learn about Moravians. It’s a living history museum that features preserved buildings, museums, and gardens that offer a glimpse into 18th- and 19th-century life, with costumed interpreters demonstrating traditional crafts and daily activities. A ticket to Old Salem includes admission to more than a dozen interpreted buildings and gardens, such as the Single Brothers’ House, where boys moved in at age 14 to learn a trade among the men.

The only way to move out was to marry or die, but before marrying, God had to approve the proposal via “the lot.” To know his will, one had to choose a paper from a vessel, and the only possible answers were yes, no, and blank — to be decided later. Girls also lived in a Single Sisters’ House, and though they had to wait until a man proposed to respond to a (pre-approved) request for marriage, they could decide against it, and the “no” was respected. Some chose never to marry and to stay with their sisters or brothers. Productivity, it seems, was more important to the community than family — though most did marry.

Also in Old Salem is the Museum of Early Southern Decorative Arts (MESDA), which showcases one of the largest collections of Southern decorative arts in the country. It’s worth a visit if you’re interested in period furnishings, guns, pottery, and the like. I’m always interested in how historical museums orient their collections, and this one is focused on European settlers. After all, the period showcased included Native Americans and enslaved people; it’s a curatorial choice to omit depictions of their daily lives. Additionally, though the Moravian Church evolved toward abolitionism and eventually apologized and sought reconciliation for its role as enslavers, the museum depicts none of this history through artifacts or stories.

Reynolda Estate. Photo: Visit Winston

If you need a bite while touring Old Salem, the Winkler Bakery is the country’s oldest continually operating bakery. It was founded in 1807 when a baker by the name of Christian Winkler took over a bakery that the Moravian Church built in 1799. It’s a fun historical stop, but the goods are more of a novelty than a flavor sensation — there are better pastries in Winston-Salem.

Across town from Old Salem, Reynolda Village and Reynolda House present another fantastic way to spend a day — and, really, I mean the whole day. This 1,067-acre estate was developed between 1912 and 1917 by RJ Reynolds and his wife, Katharine, of tobacco fame. The family home is now an American Art Museum, and the adjacent village has shopping and dining. The meticulously groomed botanical garden is free and open to the public. The whole grounds (minus the museum) are now owned by Wake Forest University. A footbridge connects the estate grounds; the presence of students in the gardens and shops is palpable and pleasant.

The village facilities were not only modeled after an English village — including a dairy barn, cattle shed, school, post office, smokehouse, blacksmith, etc. — but Mrs. Reynolds also had the village built with the same quality materials as the main house, creating a sturdy and lasting impression of how the estate might’ve looked. The restoration of the village has won awards and is listed on the National Register of Historic Places. Reynolda House is an intimately presented museum of American Art inside a historic house. Exhibits shed light on the complexities of the Reynolds’ legacy, as well. If you’re around in August, you could catch the soon-to-open Camel City: Tobacco & Transformation, 1875-1964, which highlights worker exploitation and the role of Black women in advocating fairness and trade unions.

Innovation Quarter and Sawtooth Center for the Visual Arts. Photos: Kimberly Dark

Continuing with the theme of renovation, downtown Winston-Salem has some great examples. What happens when large companies like Reynolds and Hanes (think socks and briefs) shut down US operations and move them abroad? Urban blight is the answer — but luckily not the end of the story in this case. The city’s Downtown Arts District is fun, and visitors can take a self-guided walking tour. The Sawtooth Center for the Visual Arts has fantastic facilities, and the building (a former Hanes factory) houses other arts organizations and theaters, too. Facilities include studios and instruction in woodworking, stained glass, metal, ceramics, and more. The gift shop and gallery spaces are free to the public and worth a visit to take home some authentic Winston-Salem creations.

The city’s Innovation Quarter also charmed me. The area is filled with repurposed factories serving gorgeous food and cocktails surrounding Bailey Park, where free films are shown on the lawn for relaxing picnics in the waning light of day.

600 Degrees. Photos: Kimberly Dark

Starting with Innovation Quarter, 600 Degrees is not to be missed. Both the alcoholic and alcohol-free cocktails were innovative and delicious. We tried a variety of small plates for dinner, including the hearth-roasted squash and queso, sweet potato and chickpea fritters, and tuna crudo. The Lil’ Drunken Key Lime Cake was delicious, and the service was superb.

Just a few blocks away, The Katharine Brasserie & Bar (yes, named for Mrs. Reynolds) provided a delightful downtown repast. We started with a charcuterie board worthy of its French origins, complete with three fruit compotes. The banana croissant bread pudding at the end of the meal was superlative.

For Southern fare, try Mozelle’s, where the tomato pie reigns supreme, and its accompanying succotash is a stunner. The Brussels sprout appetizer was a seared delight, and the coconut pie is almost too much at the end of a meal, but it makes for a rich treat back in your hotel room. Mozelle’s menu includes a list of farms from which the meal is locally sourced.

Now that you have dinner plans in order, let me recommend a Winston-Salem cocktail bar that serves as both entertainment and tipple. EasyTalk was founded by and is tended by artists. My bartender’s name was David, and I can see why he recently won a North Carolina bartender of the year award. EasyTalk is two bars in one. Downstairs is “easy,” with a clever menu of complex and delicious cocktails. Upstairs, you have to “talk” to get a drink — and it’ll be something that suits you in a unique way. My partner and I tried the first two ordering options. After a brief interview, David made me something like a Bluebird (a gin or vodka cocktail made with Blue Curacao), perfect for my palate. My partner rolled the dice to reveal a randomized selection, which yielded one of the best drinks we’d ever tasted. Two of the elements were smoky and sweet, and the means of arriving at the combination was complex.

Left: Mozelle’s tomato pie and salad. Right: EasyTalk Bluebird. Photos: Kimberly Dark

Reynolda Village is full of good food; even Uber drivers told us to go to the Village Tavern, where my partner had super shrimp and grits, followed by one of the best warm carrot cakes in memory. Stop a few doors down at Dough-Joe’s for made-to-order cake doughnuts. Every doughnut is served hot with your choice of glaze, drizzle, and toppings. (If you have nut allergies, you’ll be pleased that it’s a fully nut-free facility.)

The list of baked delights in Winston-Salem goes on and on. Krankie’s Coffee is built for a crowd and serves up items such as the chicken biscuit brined and fried in Texas Pete hot sauce and honey. You can even get the chicken biscuits — and anything with sausage — made vegetarian. Camino Bakery is the place for both vegetarian and gluten-free options, in addition to full breakfast and lunch. I had a chai and seasonal squash danish that were truly sublime, and my partner feasted on gluten-free quiche that didn’t spare the cream. This breakfast spot was our favorite; we stashed mock chicken salad and pimento cheese in the hotel fridge for later.

To top it all off, don’t miss Bobby Boy Bakeshop (lauded by locals and James Beard alike) and Cheesecakes by Alex if you need an afternoon snack.

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We stayed at the Kimpton Cardinal Hotel in the building that used to be RJ Reynolds’ headquarters. The first 10 floors of this Empire State Building prototype are now the hotel, and the remaining 15 floors are apartments. Kimpton is one of my favorite casual luxury brands, and this one didn’t disappoint. The wine hour hosted at 5 PM nightly includes small snacks from the aforementioned Katharine’s Brasserie. Dogs are welcome at Kimpton, and we saw them lounging as we sipped wine with Sam Cooke on the phonograph. There’s also a black-light rec room downstairs, with a two-lane bowling alley and a small basketball court under the disco ball.

Beyond the Kimpton, all of the major hotel chains are represented downtown. Hotel Indigo, which has its own local flair, is just around the corner from the Kimpton. One accommodation worth noting is The Graylyn Estate, which you can visit even if you’re not staying there. It’s close to Reynolda because Mr. Gray was the Reynolds’ second in command. The rooms lean toward period decor and estate finery, with butlers to treat you like royalty. Whether you opt for estate seclusion or the downtown arts scene, Winston-Salem is a fascinating stop for a few days. Just don’t skip the biscuits!