Arrival and Check-In 

With only 48 hours to explore, where you stay matters. Choosing accommodations downtown puts many of Winston-Salem's best restaurants, shops, and nightlife within walking distance, so you spend less time driving and more time experiencing the city. 

For a luxury stay, book a room at the Kimpton Cardinal Hotel, a pet-friendly boutique hotel housed inside the historic R.J. Reynolds Building. Hotel Indigo is another boutique-hotel option in the heart of downtown, offering stylish accommodations and pet-friendly amenities. For a more intimate stay, the historic Summit Street Inns combines the charm of a bed-and-breakfast with a convenient location within walking distance of downtown. 

There are many other options for lodging downtown, whether you’re looking for a traditional hotel or a unique place to stay. 

Browse the Downtown Arts District 

Your first stop is the Downtown Arts District, a walkable stretch of art galleries, shops, and restaurants centered around Trade and Liberty Streets. Here you can browse everything from original artwork and handcrafted jewelry to vintage clothing, home décor, and locally made gifts. Don't miss Delurk Gallery, home to Winston-Salem's first public display of the Art-O-Mat machine. These retired cigarette vending machines have been transformed into miniature art dispensers, allowing you to purchase original artwork with the pull of a knob. You can find these unique machines all over town now, so be on the lookout as you explore. Visual Index, a woman-owned shop featuring a variety of handcrafted goods, is the perfect stop with art that ranges in prices, perfect for casual travelers looking for something affordable to take home. 

For something a little more new age, browse crystals, candles, herbs, and tarot decks at CasaShanti. Just down the street, Body & Soul celebrates African and African-American culture through books, art, gifts, skincare products, clothing, and accessories, while nearby local favorite Kin & Cottage will fill your home with fragrances inspired by the South. Vintage lovers should be sure to stop in at Still Grimey and Off the Rack, where you'll find curated racks of retro T-shirts, denim, NASCAR memorabilia, and other one-of-a-kind finds. 

Have Dinner and Enjoy Live Music 

For dinner, Twisted Pine offers elevated comfort food and specialty cocktails, while Mission Pizza Napoletana serves wood-fired pizzas that have earned national recognition. For a classic steakhouse experience, The Spotted Cow Steakhouse is known for its steaks, seafood, and wine list. Looking for a more casual classic? Check out Heff's Burger Club or Camel City BBQ Factory.

Keep the good times rolling and cap off your first evening with live music. Fiddlin' Fish Brewing and Wise Man Brewing frequently host local musicians on Friday nights, and Earl's often features performances on both Fridays and Saturdays. Be sure to check out the line up at The Ramkat, where you can see everything from local acts and indie artists to popular artists. You can also grab a drink at Miller's on Trade and see who's playing. Live music schedules change throughout the year, so check out our events guide before your trip to see what's happening during your visit. Head to our Live Music Guide for even more ideas for an evening full of good vibes and great tunes.

Grab Breakfast Downtown 

Krankies is known for its coffee and breakfast biscuits, while Young Cardinal Cafe serves creative takes on classic brunch dishes. If you're looking for something a little more upscale, The Katharine Brasserie & Bar offers a French-inspired brunch menu. 

Tour Old Salem 

Before diving into the history, take a stroll through the Cobblestone Farmers Market, held Saturday mornings beside the Old Salem Museums & Gardens Visitor Center. Local farmers, bakers, and artisans gather here to sell everything from fresh produce and flowers to baked goods and handmade products. 

Officially kick off your historic tour with a stop inside the Visitor Center to get oriented, ask questions, and purchase tickets. While you can walk the historic district for free, tickets are required to enter the buildings and speak with the costumed interpreters. Admission includes access to multiple family homes, trade shops like the gunsmith and pottery workshop, the Boys' School, and other historic structures throughout the district. The galleries inside the Frank L. Horton Museum Center are also included with All-in-One admission tickets. 

Make a Lunch Stop 

Two local favorites sit within two blocks of the Old Salem Visitor Center. District 924 is known for its soul food, while East of Texas serves authentic Texas-style barbecue smoked low and slow. Stop by Lesser-Known Beer Co. nearby for German and Czech-inspired brews. If you're looking for something quick and delicious without leaving the historic district, pop into Muddy Creek Cafe for a deli-inspired menu and continue exploring!

Before hitting the road for your next stop, consider a stop in Lot 63 for a mid-day pick me up. This charming coffee shop and tap house is tucked into the historic streets of Old Salem and offers a moment of quiet reflection after a busy morning!

Try Something New at Dabble Art Bar 

If you didn't get your fill of history this morning, you're welcome to continue browsing Old Salem, but if you're looking for something new, hop in the car and head to the Historic West End neighborhood to check out Dabble Art Bar. 

This colorful spot functions as an art bar, gathering place, and gift shop where you can order supplies for a specific craft, then settle in and create at your own pace. Projects range from watercolor painting and stamp making to coloring and other beginner-friendly crafts, making it easy to participate regardless of your artistic experience. 

Art lovers should also make a stop at the new NCMA Winston-Salem space located on 4th Street downtown. The inaugural exhibit showcases the processes, practices, and natural materials of artists working across North Carolina. 

Enjoy Dinner on a Patio 

For the easiest dinner spot, head next door to Dabble to The Porch Kitchen & Cantina, where you'll find Mexican-inspired dishes, tacos, and margaritas. 1703 Restaurant & Catering is a short drive away and is an underrated spot for upscale cuisine. 

You can also return downtown and dine at Spring House Kitchen & Restaurant, a longtime favorite known for its seasonal menus inside a restored historic home. Other favorites in the downtown area include Oh' Calcutta, Di Lisios Italian Restaurant, and Jeffrey Adams on Fourth. 

Take a Ghost Tour 

As the sun sets, discover a different side of Winston-Salem on the West Endings Ghost Tour with Carolina History & Haunts. 

This guided walking tour takes you through the historic West End neighborhood, where you'll hear stories of unexplained events and infamous residents. Whether you're a believer in the paranormal or simply enjoy a good story, it's a memorable way to learn more about the city's history.

Start with Breakfast 

You'll want a hearty breakfast before getting outside this morning. Miam Breakfast House is known for its breakfast skillets and Benedicts, while Midtown Cafe & Dessertery serves everything from classic breakfast plates to stuffed French toast and omelets. Both restaurants are especially popular on weekends, so arrive early to avoid a wait. 

Get Outside with Triad ECO Adventures 

Spend the morning exploring Winston-Salem with Triad ECO Adventures. Their guided stand-up paddleboard tours on Salem Lake offer a peaceful way to get out on the water, while their e-bike and Segway tours are a fun way to cover more ground around the city. 

Guides share their passion for Winston-Salem while introducing guests to local history and small businesses they might otherwise miss. If you don't see availability online, you can arrange a tour by phone. They prefer tours to be booked at least one month in advance, and most experiences require a minimum of three people. 

Lunch in Reynolda Village 

Once part of the historic Reynolds estate, Reynolda Village is now one of the best shopping and dining hubs in the city. Theodore's Bar & Market is a popular choice for sandwiches, salads, and lighter fare. Village Tavern's original location has been serving guests here for more than 40 years. For something quick and casual, May Way Dumplings offers handmade dumplings and Chinese noodle dishes. 

Shopping in the Reynolda Road Shopping District 

Reynolda Village is the anchor for the Reynolda Road Shopping District, so spend some time browsing before heading home. Here you'll find upscale boutiques like All Through the House, Half Past Three Clothing + More, and The Bookhouse. 

A short drive away, you can browse colorful fashion, gifts, and more at The Boho Depot, shop curated home decor at Elizabeth's at Hanes Park, or pick up something for the little ones at Bella + James Children's Boutique. 

Other Suggestions

• Traveling with kids? Swap a few stops on this itinerary for family-friendly attractions like Kaleideum, where hands-on exhibits encourage learning through play. Tanglewood Park has playgrounds, walking trails, Softgolf, a large pool and aquatic center, and horseback riding. 
• Looking like rainy weather? Spend an afternoon watching a film at a/perture cinema, browsing exhibits at the NC Museum of Art - Winston-Salem, or touring Körner's Folly, one of the most unique historic homes in the country. The historic Reynolda House Museum is currently closed for renovations on the main house, but other art exhibits are open on-site. Learn about global cultures at the Lam Museum of Anthropology or browse exhibits at the Delta Arts Center, which emphasizes contributions by African-Americans.

• Visiting in the summer? Extend your time outdoors with free concerts in downtown parks and plazas, seasonal festivals like Art Crush, and water adventures at local lakes and state parks. 

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