Like most interesting Southern cities, Winston-Salem is a town entrenched in history, but it’s also one that is constantly reinventing itself. In fact it is made up of two cities, Winston and Salem, and each one has its own unique cultural history. The pair came together in name during the late 19th century (hence the minor league baseball team’s name of “The Dash”), and the combined city has about a quarter-million inhabitants. An interesting combination of old tobacco money from the R.J. Reynolds Corporation and a vibrant younger population made up of recent graduates from Wake Forest University or folks who want to take part in the artistic, cultural and professional opportunities of Winston-Salem make it a fascinating spot to visit. Of course, with a burgeoning economy comes restaurants, bars, breweries and boutiques, so here are some great spots to visit if you find yourself in Winston (as the locals call it) for a weekend.

Winston-Salem in the fall | Image:
Winston-Salem in the fall is simply stunning! Image:


Check in to the Kimpton Cardinal Hotel, a relatively new property in an historic building. The 20-story edifice that houses the Cardinal was once the headquarters of R.J. Reynolds, and the lovely Art Deco exterior was actually used as the prototype of the Empire State Building. A neat fact: The iconic Big Apple skyscraper sends a Father’s Day card to the Reynolds Building every year.

Like the baby Empire State | Image:
Like the baby Empire State Building | Image:

Many of the design elements of the hotel reflect back on the building’s history, from smoky prints on the bathroom wallpaper to an events area on the top floor, which is still preserved as the RJR boardroom where the company’s leaders met. But most of all, the lobby decor is intended to be like a cozy living room where you can pass the whole day, enjoying coffee in the morning, a hosted wine hour in the early evening and access to a fun recreation area in the basement with bowling alleys, ping pong tables and even a basketball court.

You may never even make it up to your own room | Image:
You may never even make it up to your own room. Image:

But an even better way to get a little exercise and connect yourself to the city is to make a quick jaunt over to Old Salem, a restored historic district that pays homage to the Moravians, who settled in the area during the middle of the 18th century. One of the earliest Protestant denominations, Moravians came to North America from the Kingdoms of Bohemia and Moravia, now part of the Czech Republic. Seeking a place to live, work and farm, they settled initially in Pennsylvania before looking for a place to build new congregations in North Carolina.

Walk the historic streets of Old Salem
Walk the historic streets of Old Salem for a look back at the city’s rich history.

Today, Old Salem operates as a living museum, with costumed interpreters telling the histories of the restored buildings and describing everyday life in the community. Unlike other historic districts, such as Colonial Williamsburg, these docents do not attempt to speak in the traditional language or accents of the Moravians, so you won’t hear “thee” or “thou.” They will show you how they still farm the land using ancient tools and techniques, and how they prepare their foods in open hearths.

Eat some history, too!
Get a taste of Winston-Salem history, too!

Definitely drop by Winkler Bakery to shop for traditional Moravian baked goods (cookies, bread, sugar cake, etc.) and to see them made by artful craftspeople. You could easily spend a whole day visiting all the buildings and museums in Old Salem, but it’s also an enjoyable spot to just take a stroll for an hour or so.

You can’t beat the aromas of fresh-baked bread.
You can’t beat the aromas of fresh-baked bread.

Head back to the Kimpton for dinner and a cocktail at their stylish bar and brasserie, The Katharine, named after the wife of Mr. R.J. Reynolds. The stunning bar divides the space between drinking and eating, but you can catch glimpses of the social scene from either vantage point. The cocktail program at The Katharine is pretty advanced, especially considering that North Carolina is what is called a “control state,” meaning that all alcohol must be purchased through government entities. Consequently, the bartenders’ access to some more exotic ingredients might be a bit limited, but what they lack in raw materials, they more than make up for with creativity.

In addition to great drinks, the bar area also features a raw bar stocked with seafood so you can enjoy an appetizer before retiring to the restaurant for a full meal of classic French bistro fare. Open for breakfast, lunch and dinner, The Katharine is an excellent amenity to enjoy while staying at the Kimpton Cardinal.

Katharine is the happening bar at the Cardinal.
The Katharine is the happening bar at the Cardinal.

Finish off your evening with a visit to Wise Man Brewing, named after the three founders of the operation — an attorney, a chemist with a Ph.D. and an accountant. The trio of friends banded together to refurbish an old warehouse into a very attractive space where patrons enjoy live music, outdoor games, food trucks and, of course, plenty of delicious beer. The inner workings of the brewery are visible through a large window in the taproom, and the modern brew system offers the flexibility to produce all sorts of different styles of beers to fit just about any palate. Particularly excellent are Wise Man’s pale ales, both American and IPA.

Pull up a pint at Wise Man.
Enjoy a pint at Wise Man.

And it’s dog-friendly!

I’m sure his paws were clean.
I’m sure his paws were clean.


If you’d prefer to leave the hotel for breakfast, make your way to Mary’s Gourmet Diner for a meal that is also an experience. Owner Mary Haglund opened her restaurant in an old bank back before there were many female-owned businesses in Winston-Salem. Adding her own artistic touches and quirky details like a mish-mash of plates and coffee cups plus almost 200 different sets of salt and pepper shakers, Mary created an eclectic and artsy space with an emphasis on community.

Local artists cover the walls with their work, including an immense mural of a Garden of Eden scene (complete with a dinosaur!), and the menu further fosters the sense of community by calling out the specific local farmers and purveyors who provide the ingredients for the food. The menu features organic juices, infused waters and breakfast dishes that range from healthy to decadent.

We kind of love those light fixtures!

For a little retail therapy, visit the Downtown Arts District (known as DADA, beats me where that second “a” comes from … ). Within just a few blocks, you’ll find lots of working art studios, galleries, boutiques and gift shops that are perfect places to search for a souvenir of your visit to Winston-Salem.

Another nice area to soak up some of the city’s vibes is the West End Historic Neighborhood, where the architecture still reflects what the city looked like between 1890 and 1930. Blocks of Craftsman bungalows, Classic and Colonial Revival homes and Queen Annes still line the picturesque streets. Rest your feet for a bit at Grace Court Park, a charming little green space with gazebos and benches for sitting and watching the world go by.

If you’re seeking out some fine art, the Reynolda House Museum of American Art is a must-visit. Just the building that houses the collection is worth the trip. The former home of R.J. and Katharine Reynolds, the tasteful estate is like a mini-Biltmore. Wander the grounds and gardens or explore the exhibits that show what life was like for an early 20th century millionaire. Particularly attractive this year is the gallery section of the house, which, in celebration of the 100th anniversary of the home’s construction and the 50th year of the space as a gallery, is bringing in some amazing art exhibitions.

The modern gallery space is built separate but attached to the rest of the mansion. Image:
The modern gallery space is built separate but attached to the rest of the mansion. Image:

Until November 19, the highlight will be Georgia O’Keeffe: Living Modern, a collection of some of her best paintings and photographs accompanied by actual articles of her wardrobe that demonstrate her unique style.

If Reynolda House grabs your fancy, another interesting lodging option is right across the street at Graylyn, a 55-acre resort built around the stately home of Bowman Gray, a former chairman of the board of RJR. The castle-like edifice features an indoor pool, which can be covered with a dance floor for parties; a Turkish-themed dining area with wall coverings imported from Istanbul; and a hidden poolroom and bar tucked away in the basement. Butlers are always on-call for guests’ service needs and to share the history of the estate. Plus, true to the Southern hospitality of the Gray family, there are special kitchenettes spread around the property with free ice cream available at any hour.

A night in Graylyn is like visiting Gatsby’s house.
A night in Graylyn is like visiting Gatsby’s house.

Speaking of sweets, if the word “Moravian” sounded familiar to you when you first read it, you possibly might be remembering the famous Moravian cookies. These wafer-thin treats have been around since Colonial times and come in varieties like sugar, ginger and lemon. Visit Mrs. Hanes Cookies on the outskirts of town for a tour of their plant and to meet members of the family who have been making these treats by hand for generations.

You’ll have to wait until they come out of the oven, but it only takes 10 minutes!
You’ll have to wait until they come out of the oven, but it only takes 10 minutes!

Another food item native to the Winston-Salem region is what they call “dipped chicken,” a crispy fried chicken that has been slathered with a secret sauce usually containing Texas Pete hot sauce (yet another local product, despite the geographically confusing moniker,) vinegar and Worcestershire sauce. More like a distant cousin of Nashville Hot Chicken, this bird is spicy without damaging your palate, and the best in town comes from Slappy’s Chicken.

The bird is the word!
The bird is the word!

Order up a plate with a side of their novel Cheez-It Mac ‘n’ Cheese and some soothing potato salad for a fantastic lunch.

Just spicy enough to make you sit up and pay attention
Just spicy enough to make you sit up and pay attention

Once your tummy settles from lunch, give it another challenge with a visit to Crafted — The Art of the Taco for a flavorful dinner. Offering updated street food like creative tacos, burgers and rice bowls, Crafted will take you on an international journey.

Elevating simple street food to something special
Crafted elevates simple street food to something special.

For more upscale fare, consider Spring House Restaurant, Kitchen & Bar, where Chef Timothy Grandinetti cooks up dishes from a menu that flows with the rhythm of the changing seasons and features a bounty of local ingredients fresh from the farm. The restaurant is built inside a 1920s mansion, which is still a gathering spot for downtown residents. The cozy bar area is the beating heart of the building and is perfect for enjoying a proper cocktail before or after dinner.

The bar at Springhouse is usually a hive of activity around happy hour.
The bar at Spring House is usually a hive of activity around happy hour.


Although you might not want to leave this vibrant town, all good things must come to an end. But nothing says you can’t get a little more caffeinated or enjoy one last boozy brunch before hitting the road. (Hopefully not too boozy if you’re driving.) Krankies Coffee can take care of all of your needs, thanks to a menu of rich brunch dishes including a chicken biscuit with white gravy that will challenge any in the South plus a full lineup of coffee drinks made from beans roasted in-house in addition to a full bar with beer and cocktails.

They live up to this simple mantra.
They live up to this simple mantra.

On the way out of town, stop by The Southeastern Center for Contemporary Art, a free museum in the same area as Reynolda House and Graylyn. Showcasing original exhibitions of regional modern art including dance, theatre and music, SECCA is a favorite destination for art fans from around the world.

SECCA hosts free concerts and shows on their grounds throughout the year. Image:
SECCA hosts free concerts and shows on their grounds throughout the year. Image:

They also share art with the masses through a program of Art-o-Mats, retired cigarette vending machines that have been converted to sell affordable art pieces from actual working artists.

This particular machine lives in the lobby of the Tennessee Performing Arts Center
This particular machine lives in the lobby of the Tennessee Performing Arts Center.

As a metaphor for something that is hip, artsy and fun, these machines are a perfect representation of the scene in Winston-Salem. Head there soon and discover the city in person!

Learn more about Winston-Salem and begin planning your weekend getaway


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About the Author
Chris Chamberlain