City Cheat Sheet: A Guide to Winston-Salem, North Carolina

Reynolda House and Gardens. Photography by Lauren Olinger/Red Cardinal Studio for Reynolda.

WHY SHOULD ONE VISIT THE QUAINT, BEAUTIFUL TOWN of Winston-Salem, North Carolina? The Scout Guide Triad–Greensboro, Winston-Salem & High Point editor Ashley Powell Nosek can name a few reasons. Home to Wake Forest University and a bustling downtown area, Winston-Salem has a university town verve; a vibrant arts scene showcasing excellent art galleries, notable pottery creations, and a strong emphasis on quality live theater; and plentiful opportunities to enjoy the great outdoors thanks to wonderful parks, trails, lakes, and golf courses. 

Ready to plan your next getaway (or staycation) to Winston-Salem? Read on for Ashley’s favorite local finds and activities for taking in the city.

*Please note that due to COVID-19 some of these businesses might be closed or have specific guidelines in place. We recommend calling ahead and/or visiting their websites for the latest information on their status, offerings, etc. 

WHEN TO GO // Winston-Salem is a year-round destination. However, this old southern town full of mature hardwoods, stately homes, and a growing plethora of outdoor leisure options, is particularly lovely in the fall and spring. 

The Graylyn Estate. Photography courtesy of The Graylyn Estate.

WHERE TO STAY //Graylyn (1900 Reynolda Road). You can be “king of the castle” at this estate-turned-hotel and conference center. Choose to stay in the Manor House, The Mews, or one of the cottages or bungalows. Walk right across the street to enjoy the walking trails in Reynolda Gardens or just enjoy the grounds of Graylyn.

Hotel Indigo (104 West 4th Street). Opened in 2019, Hotel Indigo is one of the newest hotels in Winston-Salem, and is true to the Indigo brand with its focus on customer service and boutique size. The on-site restaurant and wine bar, Winston Wine Loft & Restaurant, is well worth a visit.

The Kimpton Cardinal Hotel (401 North Main Street). Housed in the former headquarters of the RJ Reynolds Tobacco Company, the building served as the architectural model for New York’s Empire State Building, which opened two years after the Winston-Salem structure was complete. A fun perk of this hotel is a full indoor playground for kids and adults. You can slide down a slide, play basketball or ping pong, and even go bowling. Plus, the hotel is dog-friendly.

Reynolda House and Gardens. Photography by Lauren Olinger/Red Cardinal Studio for Reynolda.

WHAT TO DO // Reynolda House Museum of American Art (2250 Reynolda Road). Once the bungalow of the R.J. Reynolds tobacco family, this house museum holds a permanent collection of renowned works and showcases frequent traveling exhibits. Be sure to check out the bowling alley and pool! 

a/perture Cinema  (311 West Fourth Street). The only dedicated year-round, nonprofit art house cinema in the Piedmont Triad, a/perture brings first-run independent and major films to its screens. Enjoy a beer or glass of wine while you escape into a great film. 

Old Salem Museums & Gardens (600 S Main Street). Founded by Moravian settlers in 1766, at this destination you can walk cobblestone streets and meet re-enactors at each exhibit who show how they practiced their trades and home life. Each season offers unique programming, and classes are offered year-round.

The Ramkat (170 West 9th Street). The Ramkat doesn’t disappoint in its variety of live music offerings. From bluegrass to hip hop artists, the intimate setting brings you up close to exceptional local and national talent.

Recreation Billiards (412 West 4th Street). A stalwart of downtown Winston-Salem, the “Rec,” as locals call it, opened just after World War II in 1947, and the owners have maintained the historic vibe even through renovations. Stop in for a game of pool and a drink and be sure to check the schedule of live music. 

The Southeastern Center for Contemporary Art (750 Marguerite Drive). Just across Reynolda Road from Reynolda House, you’ll find tucked away at the end of a residential street an impressive collection of “the art of our time,” where SECCA houses its substantial permanent collection of visual art and offers music, dance, and theater.

University of North Carolina School of Arts (1533 South Main Street). Founded in 1963, UNCSA is America’s first public arts conservatory. They are top ranked nationally in dance, design and production, drama, filmmaking, and music. Student performances occur year-round in all five schools.

Sfeer + Co. Photography courtesy of Sfeer + Co.

WHERE TO SHOP // Sfeer+Co. (111 Reynolda Village). Sfeer+Co is a furniture store that offers a timeless collection of interior, fashion, and lifestyle goods. Interior designer and owner Laurence Buyle combines custom-made with award-winning, natural elements and sustainable materials, all to create the perfect “atmosfeer” your interior deserves. Craftsmanship and enduring design are at the core of the business. 

Fiddle & Fig (403 West End Boulevard). Located in the same building as famous local bakery Lavender & Honey and Poppyseed Provisions, Fiddle & Fig is a locally owned home goods and accessories store where you are guaranteed to find a new accessory for your home, serving piece for your next party, or a unique hostess gift.

Gazebo (107 Reynolda Village). Whether you’re shopping for a special occasion outfit, a sophisticated work wardrobe, or the latest accessories and handbags, the Gazebo has you covered. In-house alterations make it a perfect fit for your busy lifestyle, and don’t forget to swing by the Gazebo Sale Room around the corner.

Hive (304 S. Stratford Road, Thruway Center). A new and unique lifestyle store located in Thruway Center, this store offers fashionable clothing and home accessories with a uniquely Palm Beach vibe. 

McCalls (111-A Reynolda Village). Since 1925, McCalls has been filling Winston-Salem homes with special and timeless items, including gorgeous lingerie and sleepwear for ladies, beautiful infant clothing, and traditional boy and girl clothing from 2T to 6x. Additionally you’ll find fine bed, bath, and table linens by Matouk, Sferra and Fino Lino. 

Mellie & Emelia (365 Peters Creek Parkway). A fun boutique featuring contemporary and well-known women’s lines. Proprietor Courtney Myers has sourced wonderful options for everything from a casual brunch with your girlfriends to a date night out with your significant other. She also emphasizes personalized service and will not only help you find a perfect outfit, but also pair it with lovely accessories created by local artisans.

Monkees of the Village  (217 Reynolda Village). Have a party, beach weekend, or mountain getaway on the horizon? Spruce up your entire wardrobe from head-to-toe at Monkees. 

Nitsa’s Apparel (107 S Stratford Road). After fifty years in the fashion business, Nitsa’s has it all, including a complete line of sportswear and high quality, modern lines for all ages. Nitsa’s is also the place for brides—the expert staff will help the newly engaged explore all the latest in couture bridal styles. 

Norman Stockton Clothier (99 Reynolda Village). For the stylish man in your life, stop in at Norman Stockton for a full selection of men’s fashion featuring fine merchandise along with exemplary customer service and full-service tailoring. Lines you’ll find there include Alan Paine cashmere, Ballin, Canali, Heal Goods, Johnnie O, and Peter Millar. 

Rebecca & Co. (1200 Reynolda Road). Rebecca & Co. has been a contemporary clothing destination for women of the Triad since 1995. You’ll find the perfect pair of designer denim, a stand-out dress for your next event, or your newest must-have.

Theodore B. Interiors (1031 Burke Street). A full-service interior design firm and home décor concept store from a pair of interesting and fun local designers, this sweet little shop is a must-see when you’re shopping around town. You’re guaranteed to find the perfect hostess giftor accessory for your home there.  

Trouvaille Home (938 Burke Street). If you have a bold, eclectic design style, spend some time at Trouvaille. Discover funky finds from all over the world, fine fabrics and furniture, hand-selected estate pieces, and antiques complementing North Carolina-made, custom-order upholstery. Fine contemporary designs are interspersed with mid-century masters. 

The Katharine Brasserie & Bar in The Kimpton Cardinal Hotel. Photography courtesy of The Kimpton Cardinal Hotel.

WHERE TO EAT // 1703 (1703 Robinhood Road). A hidden gem in the Buena Vista neighborhood, 1703 features fine dining at night and ladies’ lunches at noon. The menu is creative, seasonal, and delicious.

Bobby Boy Bakery (1100 Reynolda Road). At Bobby Boy, the artistry alone is worth the eye candy. Stop in for the super flaky French pastries and an assortment of sweets, but consider yourself warned: they don’t last long, so get there early. And don’t miss the gorgeous paninis and such for lunch. 

Dom’s (134 N Spruce Street). New to the burgeoning culinary scene in Winston-Salem, Dom’s is a fabulous plant-based restaurant that puts a whole new spin on a meatless meal. With a diverse and varied menu featuring fresh pastas, small plates, and sandwiches, you are sure to find something that will please every member of your party.

The Katharine Brasserie & Bar  (401 N Main Street). Located inside the Kimpton Cardinal Hotel (which is the former R.J. Reynolds Tobacco Company headquarters), this delicious French brasserie offers breakfast and dinner. The cocktails and oyster bar are not to be missed.

Krankies Coffee (211 East 3rd Street). Sure, you can have coffee at Krankies, but you should also treat yourself to breakfast—and come back for lunch. The avocado toast, Texas Pete and honey chicken biscuit, and delicious Bloody Mary are must-try menu options.

Meridian (411 S Marshall Street). At this fine dining restaurant near Old Salem on the outskirts of downtown, the fresh menu is based on Mediterranean flavors and offers a tapas selection. Everything is made in-house, and reservations are recommended.

Mozelle’s Fresh Southern Bistro  (878 West 4th Street). A go-to for great food and a casual vibe, this eatery is tiny but mighty. Sourced from local farms, the menu leans toward Southern favorites but gets very creative. Favorites include the meatloaf, tomato pie, and succotash. Put it on your list for Sunday brunch.

Quanto Basta (680 West 4th Street). An Italian restaurant and wine bar with a rustic atmosphere. Get an antipasto board to share, and prepare for a generously sized entree. The beef short ribs are melt-in-your-mouth and the olive oil cake is a must-try for dessert.

Roosters–A Noble Grille (380 Knollwood Street). Locally sourced fine dining and great for groups, Roosters boasts an extensive wine list and creative cocktails.

Ryan’s (719 Coliseum Drive). This classic, old school chop house features great service, wonderful food, and an impressive wine list. Not much has changed inside Ryan’s over the years, and we wouldn’t want it to. Be sure to order a side of bacon and blue cheese Brussels sprouts for the table. 

Sweet Potatoes (607 North Trade Street). If you only go for a basket of fried green tomatoes and fried okra with a side of cornbread, you will have accomplished something. But stay for a full meal to satisfy your need for southern deliciousness.

Willow Bistro (300 S Liberty St, Suite 100). Lunch, brunch, or dinner will have you returning for another meal at this restaurant located in a cozy, unassuming spot near Old Salem that is easy to find but hard to forget. Always get the grilled romaine salad.  

WHERE TO DRINK // Broad Branch Distillery (756 North Trade Street). How could you not want to visit a place with a mission to honor Old World craft heritage and artisanal Blue Ridge Mountain distilling traditions passed down through generations of immigrants, outlaws, and other relatives? The distillery offers tours and a tasting room with a cocktail bar. 

Black Mountain Chocolate Bar (450 N Patterson Avenue). In a new location in the heart of Innovation Quarter in downtown, this is an artisan chocolate factory that doubles as a craft cocktail bar. Step inside to taste fresh chocolate treats and stay awhile to sip a cocktail and mingle with your friends in a very chill environment. 

Earl’s (121 West 9th Street). A whisky bar with a Nashville atmosphere. Outdoor seating and live music make for a boot-stomping good time. 

Fair Witness Fancy Drinks (290 4th Street East). It’s always going to be interesting at Fair Witness, where the menu always changes and bartenders are encouraged to be creative (hence menu items like “The Pepper Steve” and “The Blackberry Dealie”). Go be fancy! 

Hoots Roller Bar & Beer Co. (840 Mill Works Street). Are you ready to “enjoy the beer you were born to imbibe?” Then come sit a spell at this fun, funky, Southern, and progressive spot.

Incendiary Brewing Company (486 N Patterson Avenue). The atmosphere here can’t be beat. Located in the Bailey Power Plant near Bailey Park, they have a huge open outdoor space to enjoy.

Tate’s Craft Cocktails (279 West 4th Street). For more than 10 years, Tate’s has remained one of the best cocktail bars in town thanks to creative, fun bartenders and a slightly upscale, city vibe. Their Blackbird Julep never goes out of style. 

Vintage Sofa Bar (1001 Burke Street). There’s just something about this place. Yes, it has sofas—making it a great place to hang with a group or sit in a corner with just one friend—but it also has outdoor seating, “quiet” table sports, and one of the best charcuterie and cheese boards in town. 

Wise Man Brewing (826 Angelo Brothers Avenue). Wise Man is a great place to hang out, and if one can call a bar “family-friendly,” then this is it. It is a great place to bring kids and even your dog on a sunny weekend afternoon, and often there is a food truck to boot.

LOCAL PRO TIP // For even more options for imbibing in the Winston-Salem area, check out The Scout Guide Triad’s cheat sheets for local Wineries and Breweries available on the city website here.

For additional recommendations for what to do, see, and experience in Winston-Salem, follow The Scout Guide Triad on Instagram