1. Step Back in Time at Old Salem

Start where Winston-Salem began. Old Salem Museums & Gardens is a living history district that brings the 18th century to life through costumed interpreters, hands-on experiences, and remarkably preserved buildings. Founded by the Moravians, a Protestant group known for craftsmanship, Salem quickly became one of the South’s most industrious early settlements.

Today, the nearly 100-acre historic district is free to explore at your own pace, with cobblestone streets, heirloom gardens, and more than 100 restored structures. For a deeper dive, purchase a ticket to enter interpreted buildings like the Single Brothers House and Salem Tavern, where daily life unfolds through demonstrations and storytelling.

Begin at the Visitor Center, then cross the iconic Heritage Bridge into the village. Before you leave, stop by Winkler Bakery for Moravian sugar cake, or grab lunch or coffee at nearby spots like Lot 63 or Muddy Creek Café. To help plan your visit, be sure to check our insider guide, Old Salem 101.

• Bonus Stop: Bethabara: Just 15 minutes north of Old Salem, Historic Bethabara Park marks the Moravians’ first settlement in the South (1753) and makes an easy add-on. Start at the Visitor Center, then explore the restored Gemeinhaus, gardens, historic structures, nature trails and more. Admission is free, with $5 guided tours offered most days. 

2. Discover Reynolda: Art, Gardens, Shopping

A visit to Reynolda offers a myriad of unique experiences in one easy stop. Start at Reynolda House, built in 1917 for tobacco tycoon R.J. Reynolds and his family. Today, it’s part art museum, part history museum, and an absolute must-see. The home’s 64 rooms feature an exceptional collection of American art alongside family artifacts, fashions, and period furnishings.

Just steps away, Reynolda Gardens invites you to slow down among dazzling formal gardens, wooded trails, a waterfall/wetlands area, and a historic greenhouse. The gardens are open daily and free to explore. Next, wander into adjacent Reynolda Village, where former estate buildings now house boutique shops and inviting restaurants. Browse spots like Monkee’s, Half-Past Three, and The Bookhouse, then settle in for a meal at Village Tavern or a sweet treat from Dough-Joe’s, recently named one of America’s Top 50 Doughnut Shops on Yelp.

All combined, the 170-acre Reynolda estate blends history, art, and everyday indulgence into one of Winston-Salem’s most memorable experiences.

• Note: Much of Reynolda House is closed for renovation through August 2026, yet the gardens, village, and art exhibit space (the Babcock Wing) remain open.

3. Stroll Through the Downtown Arts District

Winston-Salem’s Downtown Arts District is where the city’s creative spirit takes center stage. Just a few blocks along Trade and Liberty Streets, this walkable district doubles as an open-air gallery filled with bold murals, sculptures, and ever-evolving installations. Start at Artivity on the Green, a half-acre park known for its striking red “smokestack” towers and rotating mural wall. For a guide to understanding the city’s art scene a bit more, check out our City of Arts & Innovation overview.

Beyond the public art, the district is packed with galleries, shops, and local flavor. Browse handcrafted works at Visual Index or Piedmont Craftsmen, explore eclectic finds at CasaShanti, Still Grimey, and Major Tomms, or visit staples like Body & Soul, Just Be, and Mast General Store. For an overview of the retail options, check out our Arts District-centric Shopping Guide.

When it’s time to recharge, you’re surrounded by solid options. Try award-winning Mission Pizza, settle in at Twisted Pine, or grab Lexington-style barbecue at Camel City BBQ Factory. For drinks, head to Single Brothers or Broad Branch Distillery, or keep it low-key at Chad’s Chai & Tea Shop.

4. Snap Up the City’s Most Iconic Spots

Winston-Salem is full of photo ops that feel distinctly local, from historic landmarks to unexpected roadside icons. Aside from Artivity on the Green, start in Old Salem at the 120-foot Heritage Bridge, where wooden trusses and glowing Moravian stars (seasonal) create one of the city’s most recognizable backdrops. A short walk away, the 12-foot Mickey Coffee Pot marks the gateway to Old Salem and delivers a quirky, can’t-miss shot.

In the Southside, the 1930 Shell Service Station stands as the last of its kind, its yellow clamshell design making it a true roadside icon. For an awe-inspiring view, head to Quarry Park, where a 100-foot observation deck overlooks the former quarry, offering dramatic skyline views and deep-blue water below. Don’t miss the “love locks” along the railing, a signature touch to the scene. 

Want more options? Check out our guide to Winston-Salem’s IG-Worthy Spots.

5. See It All with Triad ECO Adventures

Winston-Salem offers no shortage of ways to explore, but one of the easiest ways to experience it all is with Triad ECO Adventures. Their guided tours blend storytelling with movement, giving you a deeper feel for the city in just a few hours.

Located just five minutes south of downtown along the Salem Creek Greenway, it’s an ideal starting point. Choose from 2–3 hour excursions by eBike or Segway, cruising through downtown, Old Salem, and connected greenways. In warmer months, paddleboard tours at Salem Lake offer a fresh perspective from the water. Prefer a relaxed ride? Triad ECO Adventures’ sister company, Triad Trolleys, offers narrated tours of the city’s highlights.

6. Spend a Day Outdoors at Tanglewood Park

Winston-Salem is surrounded by great outdoor spaces, but Tanglewood Park stands apart for the sheer variety of experiences in one place. Just 15 minutes from downtown, this 1,100-acre park is built for full-day adventures.

Start on the trails, where paved paths and wooded routes wind past pastures, forests, and the Yadkin River. The Arboretum is a must-see, with 26 themed gardens and vibrant seasonal blooms. Golfers can take on two championship courses, while beginners can opt for the Par 3 or playful Softgolf, where oversized clubs and foam balls create what’s been dubbed “the world’s most fun golf game.”  

Speaking of family fun, kids will love the park's multiple playgrounds, a vintage locomotive (perfect for photo ops), and lakeside views at Mallard Lake, where pedalboats are available in the warmer months. Seasonally, Tanglewood's Aquatic Center is a true destination, with spray-grounds, multiple slides, a lazy river, and more. For something different, book a trail ride or pony ride at Tanglewood Stables, available daily (reservations recommended), or relax on the deck at the park’s new golf clubhouse, which features a snack bar and grill.

To help plan your visit, check out our 24-hour Guide to Tanglewood Park.

7. Get Outdoors Without Going Far

You don’t have to leave the city to find a change of scenery. Winston-Salem’s growing network of greenways makes it easy to explore on foot or by bike.

Start on the Downtown Strollway, a 1.2-mile path connecting the heart of downtown to the Salem Creek Greenway. From there, a network of connected trails stretches for miles, linking neighborhoods, parks, historic sites, and natural areas. This includes the popular Salem Lake Trail, a peaceful 7-mile loop that traces the edges of Salem Lake and feels worlds away, though it’s only minutes from downtown. It’s especially popular for biking, offering a smooth, scenic ride that’s easy to enjoy at your own pace.

If you’re craving something more elevated, head about 20 minutes north to Pilot Mountain State Park. There, trails like the Pilot Knob loop and Little Pinnacle Overlook deliver sweeping views and a true mountain experience just minutes from town. 

For more on the city's outdoor experiences, check out our newly launched Outdoors Adventures page.

8. Go on a DIY Craft Draft Crawl

Winston-Salem’s downtown is built for brewery hopping, with eight craft breweries packed into a highly walkable footprint. Start at Foothills Brewing, then head to Industry Hill, where Fiddlin’ Fish, Wise Man, and Radar sit just steps apart. Continue to Joymongers, Lesser-Known, and Small Batch, each offering its own take on the local scene. For more on the breweries or to chart your own course, check out our Craft Draft Crawl itinerary.

Not a beer drinker? No problem. Many spots offer non-alcoholic options, including house-made NA beers and Bingo Bango soda. Several are also family-friendly, especially Incendiary Brewing, known for its expansive outdoor courtyard.

9. Catch a Game, Race, or Rivalry

In Winston-Salem, sports are a year-round affair. In spring and summer, catch a Winston-Salem Dash game at award-winning Truist Stadium, where skyline views, fireworks, and themed nights add to the experience (check out our Dash 2026 Insider's Guide for the best ways to experience a game). Or for something truly memorable, head to Saturday night race at Bowman Gray Stadium — aka “The Madhouse” — an adrenaline-fueled experience you won’t soon forget. 

In cooler months, the Twin City Thunderbirds bring high-energy, family-friendly hockey to the Fairgrounds Arena. And don't forget about college sports, with Wake Forest delivering ACC football and basketball, and Winston-Salem State offering electric HBCU game-day atmospheres.

10. Take a Walk on the Spooky Side

Most cities wouldn’t put a ghost tour on a first-timer’s must-do list. But then again, not every place has a history like Winston-Salem or a tour company like Carolina History & Haunts. 

Their tours blend local lore with well-researched history, creating an experience that’s both eerie and insightful. These guided walks wind through the Historic West End, where grand homes and quiet streets set the stage for tales of curses, unexplained encounters, and centuries-old secrets. Tours run year-round on most nights and last about two hours. Reservations are required.

• Ghosts not your thing? No problem. Explore more Top Guided Tours in our Visitor Guide feature.

11. Stay Somewhere Steeped in History

Winston-Salem offers an impressive collection of historic inns and hotels, from Art Deco landmarks to intimate B&Bs, each blending character with modern comfort.

It starts downtown with the Kimpton Cardinal Hotel, set inside the iconic 1929 Reynolds Building, a striking Art Deco tower that served as the prototype for the Empire State Building. Just steps away, the 1929 Pepper Building is another architectural standout, now home to the boutique Hotel Indigo. 

Also downtown, the Historic Brookstown Inn offers a different kind of charm, with exposed beams, original brickwork, and cozy rooms inside a restored 19th-century cotton mill. 

For something more grand, head to Graylyn Estate, a castle-like retreat set on 55 rolling acres, where storybook architecture meets upscale amenities, earning it recognition as one of the top boutique hotels in the country. Smaller stays shine, too. The Shaffner Inn and Summit Street Inns offer intimate accommodations inside beautifully preserved historic homes, while Zevely Inn places you right in the heart of Old Salem for a fully immersive stay.

Learn more about these and other historic overnight options in our Historic Stays Guide.

Hungry For More? 

You’ve got the highlights, now make sure you get a good taste. 

From Moravian treats to Carolina BBQ to Southern specialties, the city's food scene is a big part of the experience. Start with our Dining FAQ, a helpful primer on what to eat and how to navigate the scene. For more dining and drinking inspiration, explore our Food & Drink page and start planning your next meal.

Want more things to see and do in Winston-Salem? Check out our 2026 Visitor Guide for insider tips, trip itineraries, helpful resources, and more. You can pick one up in person at our Visitor Center (200 Brookstown Ave.), or view it digitally on our Visitor Guide page.