Getaway Guide to Winston-Salem, NC

Past meets present in Winston-Salem.

Winston-Salem may be called the Twin City because of its dual heritage as two separate cities (Winston and Salem, natch), but its split persona can also be seen in the way it seamlessly blends the old and new—honoring its rich tobacco industry history (hey, Camel City!) while staying relevant with modern innovations and a lively spirit.

To boot, there’s no shortage of James Beard-nominated restos, popular breweries, bold arts and cultural attractions, funky fests and events, live music venues, gorgeous green spaces, and meaningful museums—all making the central NC destination worthy of a ~two-hour road trip from Raleigh time and time again. Here’s where to start to forge your own bit of history. 

DO

Roar

“Where the Roaring ’20s come to life,” this entertainment center serves up a mix of nostalgic and modern gaming for the whole fam. Fuel your competitive side with arcade games, bowling, mini golf and more—NTM outdoor games on the lawn, also complete with a dog park. And when you inevitably get thirsty, hit up the 90-tap self-serve beer and wine wall, three full-service bars, or rooftop club with city views and VIP cabanas. Talk about a *roaring* good time! roarws.com

Reynolda Village

Take a stroll through history via charming historic buildings that once housed dairy barns, a school and post office, a blacksmith shop—you get the gist—but are now home to unique eateries and boutiques, including Dough-Joe’s Doughnuts & Coffee, May Way Dumplings, antique shop All Through the House and Half Past Three boutique. reynoldavillage.com

Downtown Arts District

Culture vultures are gonna wanna strap on their walking shoes to jaunt around downtown’s hip artcentric area feat. working studios, galleries, shops, residences, restaurants and nightlife. First Fridays provide even more reason to gallery hop—and rest assured there’s plenty of coffee (and wine!) nearby to keep you sharp. dadaws.net

EAT

Mission Pizza Napoletana

Your mission is simple: Pull up a seat at the counter and order a couple fresh-from-the-customized-Stefano-Ferrara-oven Neapolitan pies—and maybe a small plate or two. Then sit back, relax and revel in all its glory. Think a simple—but mindful—rotation of perfectly cooked blistering pies ranging classic Margherita to the Bianche made with guanciale, smoked mozzarella, black pepper, lemon zest and arugula. The award-winning (hey, best pizza in NC by Food & Wine!) self-dubbed “not a pizzeria” also serves up fresh salads, pastas and an off-menu “pizzakase” experience in which you leave your fate in the kitchen’s hands. mpnws.com

Sweet Potatoes

“Well shut my mouth!” It doesn’t get more Southern than the comfort food-with-a-twist this two-time James Beard semifinalist is serving up for lunch and dinner—from fried green tomatoes and collard green dip to BBQ shrimp and grits and a riff on fried chicken and waffles (served with sweet potato waffle fries in lieu of your standard breakfast staple). Naturally, the dessert is def worth saving room for. sweetpotatoes.ws

Heff’s Burger Club

This burger haven touts an MO of “fine food, no fuss”—and its Black Angus smashburgers are nothing short of exceptional. Get your fill with the Ladykiller (American cheese, red onion, pickles, lettuce, black garlic special sauce) or Figgy Pop (cheddar, red onion, hickory-smoked bacon, honey-Sriracha cream cheese, fig jam)—to name just a couple of cheesy ops. And the chili cheese fries are an a no-brainer. heffsburgerclub.com

DRINK

The Katharine

Whether nightcap or predinner, a bev at Kimpton Cardinal Hotel’s on-site French-inspired bar/bistro is a must. Choose from barrel-aged cocktails, alcohol alternatives and house signatures—with beer and wine to boot—or get real fancy with a Cubism Cocktail, aka your favorite spirit poured over a Sazerac- or old-fashioned-inspired cube. katharinebrasserie.com 

Krankies Coffee

Converting cranky wakers to bona fide morning people since 2003 is this hipsteresque coffee roaster/cafe beloved for “waking up Winston.” Come for a fresh cup of joe (or any of the signature house drinks: blueberry chai, Brazilian lemonade, etc.), and stay for the popular biscuit sandwiches and other baked goods. krankiescoffee.com

Earl’s

Live music and whiskey? Say less. Come out (almost) every weekend to groove to tunes while sipping on house ’tails, wine or beer. Pro tip: The Two-Step—aka a shot of house whiskey and a High Life Pony—will definitely get you in the dancing mood. Further fuel your moves with elevated bar food—plus brunch. earlsws.com

STAY

Kimpton Cardinal Hotel

Swanky meets spunky—with a sprinkle of Southern charm—at this lavish hotel located within the historic art deco-inspired Reynolds Building, aka the former home of the R.J. Reynolds Tobacco Company HQ. Serving as the architectural inspo for the Empire State Building (!), its charming spaces are ideal for tucking into after a day on the town. thecardinalhotel.com

Graylyn Estate

It’s giving Disney. Lap up luxury while living like a queen/king at the No. 4 best boutique hotel in the U.S. as voted by USA Today Readers’ Choice Awards, situated on an enchanting 55-acre estate. Through the 15th century French-carved doorway you’ll be treated to well-appointed rooms; world-class dining experiences; and a pool, trails, courts and other outdoor activities—NTM unlimited complimentary ice cream (really). graylyn.com

The Historic Brookstown Inn

Originally the Salem Manufacturing Company circa 1837—then one of the first mills in the South to use electric lighting—the historic building has since been restored into a charming inn fit for a romantic getaway or family stay. Old meets new in the cozy rooms, while Southern hospitality is honored during a nightly wine and cheese + freshly baked cookies before bed. brookstowninn.com