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Weekend Guide to Winston-Salem, North Carolina

December 15, 2016 By Caroline Eubanks Leave a Comment

Downtown Winston-Salem
Downtown Winston-Salem

Originally settled in the 1700s by the Moravian Church, Winston-Salem brought together two separate cities. It developed throughout the 1800s and 1900s with the rise of the tobacco industry as companies like R.J. Reynolds.

It became one of the largest cities in the region throughout the 1920s and is a part of the area known as the Triad, which also includes Greensboro and High Point. Companies like Wachovia and Krispy Kreme also started in the area.

This post contains affiliate links.

What to Do in Winston-Salem

Old Salem
Old Salem

Old Salem Museums & Gardens– Before there was Winston-Salem, there was Salem. The historic buildings have been restored to serve as a living history museum, completed with interactive exhibits and costumed docents. 900 Old Salem Road

Kaleideum– Younger visitors will appreciate the interactive exhibits at the science museum, which has a planetarium, animal habitat, walking trails, and butterfly gardens. 400 West Hanes Mill Road

Reynolda House Museum of American Art– Set in the home of R.J. and Katharine Reynolds of tobacco fame, this museum features some of America’s most notable artists, from Mary Cassatt to Georgia O’Keeffe. There’s also an adjacent botanical garden. 2250 Reynolda Road

Reynolda
Reynolda

Southeastern Center for Contemporary Art– Visit this museum, which features a large collection of works of all media, primarily from Southern artists. 750 Marguerite Drive

Taste Carolina Food Tours– Experience the best of the city’s restaurants as well as history through a food tour. The Sunday walking tours go to eight eateries. Book your Winston Salem Food Tour here. Leaves from Foothills Brewing

Wineries– The city is located near the Yadkin Valley, one of the state’s best wine regions. Nearby vineyards include Raffaldini Vineyards & Winery, Childress Vineyards, and Round Peak Vineyards.

Where to Eat in Winston-Salem

Krankies
Krankies

Ardmore Coffee– Owned by two local college graduates, this shop is a cozy, locally‑owned café offering specialty coffee, creative seasonal drinks, and baked goods. 1316 South Hawthorne Road

Bobby Boy Bakeshop– Fans line up early to get a taste of these delicious pastries, including eclairs, baguettes, and daily sandwich specials. 1100 Reynolda Road, (336) 955-3284

Bossy Beulah’s– Bossy Beulah’s is a chef-driven chicken sandwich concept launched in 2019, inspired by the owner’s great-aunt Beulah. The chicken sandwich is served on Duke’s mayo, with hand-cut fries. 1500 West First Street, (336) 606-6505

Camino Bakery– With three downtown locations, this is where you go for your carb fix. Their menu features pastries and desserts, healthy sandwiches, and quiches for a quick lunch. 310B W Fourth Street, (336) 721-9990

Crafted, The Art of the Taco– This popular restaurant serves modern takes on tacos, including Korean short rib, Cuban pork, and fried chicken. They also have burgers and craft cocktails. 527 North Liberty Street, (336) 955-2458

East of Texas– The Tex‑Mex barbecue-style spot has a wide family-friendly courtyard that plays evening movies and a menu of Western favorites. Come for the smoked meats by night or for brunch of breakfast tacos. 907 South Broad Street, (336) 422-7076

Heff’s Burger Club– Founded by locals Heather (“Heff”) and Justin Webster, the high-quality burgers using grass‑fed Angus beef from Joyce Farms and artisan buns from Annie’s Bakery in Asheville earned this casual spot a James Beard semifinalist title. 285 West 4th Street

Hops Burger– On the other end of the spectrum is this humble burger joint with funky toppings like fried onion rings and mango salsa. You can also build your own burger or choose the weekly selection, best paired with a North Carolina beer. 901 Reynolda Road, (336) 842-5771

The Katharine Brasserie– Located in the Cardinal hotel, this chic restaurant is named for the matriarch of the Reynolds family. The French-inspired eatery serves breakfast, lunch, and dinner as well as cocktails and brunch. 401 North Main Street, (336) 761-0203

Krankies Coffee– This large coffee shop is recognized by the giant disco ball outside. Inside you can enjoy coffee and beer, along with sandwiches and salads. 211 East 3rd Street, (336) 722-3016

May Way Dumplings– For a quick bite after visiting Reynolda, visit this Chinese restaurant for its pork buns, dumplings, and sesame noodles. 113 Reynolda Village, (336) 782-8773

Milner’s American Southern Restaurant– This family-owned restaurant serves the best of Southern cuisine with modern techniques. Pair your meal with a glass of wine and enjoy live jazz music on weekends. 630 South Stratford Road, (336) 768-2221

Porch Kitchen and Cantina– The lively Tex-Mex restaurant is set in a former mill building, serving burgers, “puffy” tacos, and delicious margaritas. 840 Mill Works Street, (336) 893-8361

Slappy’s- The no-frills chicken shack is the best spot for North Carolina–style “dipped” fried chicken, fried pieces coated in a spicy-sweet glaze. Enjoy classic Southern sides and the casual setting. 200 West Acadia Avenue

Where to Stay in Winston-Salem

Brookstown Inn
Brookstown Inn

Augustus T. Zevely Inn– This bed and breakfast inside the Old Salem Historic District has antique furnishings in the cozy rooms and a daily breakfast. It’s within walking distance of local attractions. 803 South Main Street

Graylyn– The former residence of Mr. and Mrs. Bowman Gray is now a hotel and conference center run by Wake Forest University. It has 85 guest rooms in the 1930 estate or its adjoining cottages. 1900 Reynolda Road

The Historic Brookstown Inn– This historic inn, set in a Moravian mill, has comfy bedding and large living spaces. Forty guest rooms that include free WiFi, flat-screen televisions, and coffee-makers. Read our review here. 200 Brookstown Avenue

Hotel Indigo Winston-Salem– Located in the historic Pepper building, the property takes on an Art Deco-style inspiration. It has an in-house restaurant, wine bar, and pet-friendly rooms. 104 West 4th Street

The Kimpton Cardinal Hotel– Opened in the former R.J. Reynolds building, this stylish hotel offers hip furnishings and common areas. It has its own restaurant and “rec room” with bowling and foosball. Read our review here. 401 North Main Street

Camping- Nearby Hanging Rock State Park offers the closest campgrounds to Winston-Salem. The facility also has RV and tent sites. 

Rentals- Airbnb allows you to rent an apartment or house during your stay for a more local experience. It’s perfect for groups or if you just want some extra privacy.

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Filed Under: North Carolina, Winston-Salem Tagged With: north carolina, weekend guide, Winston-Salem

About Caroline Eubanks

Caroline Eubanks is the editor of this website, a Lowell Thomas award-winning travel writer, and the author of This Is My South: The Essential Travel Guide to the Southern States. Her stories from the South have appeared in National Geographic Traveler, Afar, Thrillist, Roads and Kingdoms, and BBC Travel.

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