20+ of the Most Fun Things to Do in Winston-Salem (Great Food, Wonderful Hotels, and More!)

Last Updated on September 14, 2022

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Thanks to all the fun things to do in Winston-Salem, we just can’t stop coming back to this North Carolina city. There’s a great mix of historic and contemporary pride displayed in the city’s museums, its food and arts scenes, and more.

We think at least a weekend in Winston-Salem (either around downtown, Wake Forest University, or elsewhere) will get you hungry enough to keep coming back as we do, either in the form of return stays or quick day trips.

At least that’s what we’ve learned and once you see all the bucket list-worthy stuff we’re going to share here, you’ll most likely want to do the same.

Read More: Central North Carolina (100+ Amazing Places to Visit)

Where is Winston-Salem?

  • Winston-Salem is located in Forsyth County.
  • It is the Forsyth County seat and the second largest municipality of the Piedmont Triad region.
  • The population of Winston-Salem is 679,948, making it the 4th largest metropolitan area in North Carolina.

The History of Winston-Salem

Old Salem NC Winston-Salem NC Image
Old Salem.

One of the first things to do in Winston-Salem is to understand its background. Here’s a quick history of Winston-Salem for you:

  • Originally settled by a group of German Moravians, Winston and Salem were once two separate towns that converged in 1913.
  • That’s why their minor league baseball team is called the Dash—by the way, watching them play is a fun thing to do, which we’ll get to in a bit.
  • Winston-Salem’s claim to fame is mostly for the cigarette production coming out of RJ Reynolds Company. Though it’s known as “Camel City,” tobacco isn’t the only thing Winston-Salem is known for!
  • The first Krispy Kreme opened in Winston-Salem and you can even tour the factory (See “Family Fun”) and learn more about the famous sweet confection!

Read More: Historic Towns in North Carolina

When to Visit Winston-Salem

The best times to visit Winston-Salem and Central North Carolina are during Spring and Summer. Since there are tons of things to do, June, July, and August remain the busiest months to spend time in Winston-Salem.

However, the winter months still have warm days and some people have figured out the benefits of off-season travel. Don’t discount fall, too!

With temps sometimes hitting in the 80s, hotel prices drop and fewer visitors come to the area. However, you’ll find plenty of activities for every season in Winston-Salem.

Where to Stay in Winston-Salem

Before exploring all the amazing things to do in Winston-Salem, you’re going to need a nice place to stay.

Read More: Historic Hotels in Winston-Salem

The Cardinal Hotel

Hotels in Winston Salem nc Kimpton Cardinal Image
Overlooking the Innovation Quarter from The Cardinal Hotel.

If you’re really wanting an experience clothed in history, there’s no better place than The Cardinal Hotel in downtown Winston-Salem.

The historic RJ Reynolds building was converted into this boutique luxury hotel, complete with a bowling alley, basketball court, and ornate fixtures.

It’s also pet-friendly and steeped in subtle details that frame the masculine memories of important boardroom meetings and the future of tobacco production.

Read More: Our Favorite Hotels in North Carolina

Graylyn Estate

If you are seeking luxury, the Graylyn Estate is definitely where you want to lay your head. Formerly the home of one-time RJ Reynolds chairman, Bowman Gray and his wife Nathalie, Graylyn was built in 1925 and originally sat on 87 acres as part of the Reynolds Plantation.

Now, the Norman Revival Style hotel features 85 unique guestrooms on its vast and beautiful 55-acre estate. Each room is uniquely decorated so one’s experience differs upon each visit.

Read More: Romantic Getaways in North Carolina

Things to Do in Winston-Salem (Annual Events)

Here are some of the best annual events to consider when planning your trip. There is never a shortage of stuff to do! Many are downtown Winston-Salem events that showcase the inclusivity and diversity of the city.

Bookmarks Festival of Books and Authors (September): Meet your favorite author at the largest book and author festival in the Carolinas. Bookmarks, a literary arts non-profit and bookstore, hosts this event in downtown Winston-Salem each fall.

Carolina Classic Fair (September to October): The second largest agricultural fair in the state, Carolina Classic Fair is a 10-day event with carnival rides, games, exhibits, concerts and deep-fried concessions. It should be at the top of your list of fun things to do with kids.

Festival of Lights at Tanglewood Park (November to January 1): Drive into a winter wonderland filled with more than a million twinkling lights at this annual holiday event. Plan to take this self-guided tour before the holidays or up until the first day of the new year.

Gears and Guitars (September): Billed as one of the country’s most prestigious bicycling events, join the biggest party on wheels for a weekend of racing, local riding and live music in the city of Winston-Salem.

Hispanic League FIESTA (September): Spend the day in downtown Winston-Salem celebrating Hispanic culture with live music, games and food during FIESTA, the largest street festival of its kind in the Triad. Admission is free.

Juneteenth Festival (June): Celebrate African American heritage and freedom with music, dance, panel discussions, food, and arts and crafts at Bailey Park in downtown Winston-Salem.

National Black Theatre Festival (Summer): Thespians and patrons alike can enjoy this multi-day festival showcasing performances, films, poetry, seminars and workshops that engage and enrich the community.

The Nutcracker (December): Students from the UNC School of Arts produce this holiday classic, which can be added to your list of date ideas in Winston-Salem. Who can resist the magical story of Clara and the nutcracker who comes to life?

Piedmont Craftsmen’s Fair (November): The Southeast’s finest craftsmen display their wares at this downtown Winston-Salem event. It’s a great place for shopping for unique home goods, jewelry, glassware, ceramics, furniture and decor.

Pride Festival & Parade (June): All are welcome to downtown Winston-Salem to celebrate the local LBGT community during the Pride Festival. The daylong event features a parade, live music, entertainment, hands-on activities and street vendors.

RiverRun International Film Festival (Spring): Add this to your list of fun things to do inside! Spend hours watching films, documentaries, animated shorts and other movies from various genres during this popular film festival.

Winston-Salem Open (August): The WSO is the last event before the US Open each year. The world’s top tennis players come to the city of Winston-Salem to compete in the tournament.

Year-Round Things to Do in Winston-Salem
(Historic Attractions)

We don’t want you to think the rest of the city isn’t historic, but these two things to do in Winston-Salem will take you back to two interesting eras. One of the best things about the city is its history.

Old Salem

The twin cities wouldn’t exist without Old Salem. Settled by Moravians, this tiny town gives us a glimmer into life in the 18th century. As the property and land were owned by the church, many of the townspeople of Salem fine-crafted trades to generate revenue.

Moravian Star in Old Salem

You can stroll through Old Salem for free or you can purchase a ticket that grants you access to the workshops and to craftspeople dressed in period garb who specialize in everything from baking, blacksmiths, quilting, or pottery. It’s really cool to learn from these people, so we suggest getting a ticket from the Visitor’s Center.

Bonus Challenge: Try to walk through Winkler Bakery without buying something.

Read More: Unique Things to Do in North Carolina

Tour Reynolda

Winston Salem Reynolda outside

One of the best things to do in Winston-Salem is visiting the historic Reynolda House.

Not only does it serve as a museum for incredible American Art, but guests can tour the house as it was designed and decorated by the Reynolds family in 1917. During your tour, you’ll learn about the significance that Katharine Reynolds played in the design of the house as well as her influence on working conditions in her husband’s factories.

Winston Salem Reynolda

Complete with a bowling alley, squash court, indoor pool, and luxurious interior design, you can transport yourself back to a time and place where one of the wealthiest families in America lived and entertained.

Reynolda House Winston-Salem NC From a Distance Image

The nearby gardens have some cool designs and are a great spot for throwing down a blanket and relaxing for a while. Plan to spend at least an entire morning or more exploring the house and even more time enjoying the village shops, gardens, and trails.

Read More: Amazing Museums in North Carolina

Things to Do in Winston-Salem

Many of the best things to do in Winston-Salem happen downtown. Here, you’ll find a mix of older buildings and new ones that continue to pop up throughout the city.

Things are really happening, and you can find something fun just about everywhere.

Read More: Day Trips from Raleigh

Explore Winston-Salem’s Arts and Culture

From the colorful streets and murals, Winston-Salem is renowned as a city of art. Home to the North Carolina School of the Arts, there are plenty of interactive ways for visitors to enjoy the art and culture of the twin cities.

Walk Around the Downtown Arts District

Winston Salem arts district

The Downtown Arts District Association (DADA) is located between Trade & Liberty Street and is composed of working studios and art galleries.

You can hop on a gallery tour or just wander through the Art Trail and even bring something home with you! Take a moment to chat with some of the artists that bring beauty and spark creativity into Camel City!

Winston Salem Art District

Read More: Day Trips from Durham

Art-o-Mat

If you’ve seen one, you’ll know it.

The art-o-mat was created by Winston-Salem’s Clark Whittington as a way to give art back to the people. Using the city’s plethora of now unused cigarette vending machines, Whittington repurposed the machines to disperse cigarette pack-sized art. 

The first Art-o-mat was installed in 1997 and now they appear all over the country including inside the Whitney of American Art. Artists contribute small pieces of work that can be bought through the machine for $5. See the Art-o-mats in more than 200 venues across the US or stop in Whittington’s Delurk Gallery

Stop in the Piedmont Craftsmen Gallery

Winston Salem Piedmont Craftsmen

The Piedmont Craftsmen is a guild of 400 area artists all under one roof. Over 250 of these artists display their work in the shop in the Winston-Salem arts district. This is an excellent way to browse fine craft art and support local area artists! The Piedmont Craftsmen also participate in an annual craft fair held every November since 1963!

Bookmarks (Buy Books and Support the Community)

Visit and buy something from Bookmarks and you’ll be supporting one of the only non-profit bookstores in North Carolina. In case you’re wondering how- purchases here go toward outreach programs in the local community.

The help doesn’t stop there, as you can round up orders and connect more Bookmarks members with authors and books. Pulitzer Prize and other award-winners love to frequent Bookmarks and share their experiences with attendees at events throughout the year.

Get Creative at Sawtooth School of the Arts

Sawtooth School for the Visual Arts is a non-profit art school for the community and is an excellent place for visitors to Winston-Salem! Whether you’re looking for something creative to do in Winston-Salem or just interested in trying something new- Sawtooth offers classes and workshops in eleven visual arts and crafts. 

Winston Salem Sawtooth

Check their calendar and take a class in ceramics, drawing, painting, digital arts, glass, metals, lapidary, photography, printmaking, textiles, and wood! 

Visit the Shell Station

How many times have you been told to visit a gas station while visiting a new city? Well… visiting the clamshell gas station is one of my favorite things to do in Winston-Salem!

Constructed in the 1930s, the unique clamshell shape was a quirky marketing move by Quality Oil. Located at the corner of Sprague and Peachtree Streets in Winston-Salem, you can’t pump gas here anymore. But thanks to preservation efforts, this unique North Carolina landmark now has a small museum inside and makes for excellent selfies. 

Read More: The NC Museum of History in Raleigh (+7 Things We Love About It!)

Family-Friendly Things to do in Winston-Salem

Go to a Dash Game

Sitting inside Foothills Brewing’s Downtown Taproom is one of our favorite things to do in Winston-Salem any time of year, but especially before a Dash game when the season is going.

Shuttles to the ballpark run on Thursday, Friday, and Saturday and they start right next to Foothills!

Read more: Batter up! Minor League Baseball in North Carolina!

Kaleideum Downtown

Things to do in Winston Salem NC Krispy Kreme Kaleideum Image

Looking for some family-friendly things to do in Winston-Salem? Try spending a day at Kaleideum Downtown (formerly the Children’s Museum of Winston-Salem). The downtown location features exhibits rich in STEM and the very popular Krispy Kreme Doughnut Factory. When you’re craving a sweet treat, it’s one of the best places to eat in Winston-Salem.

More Things to Do in Winston-Salem

Beyond downtown and the two major historic attractions, here are a few more ways to enjoy Winston-Salem.

Bailey Park

Winston Salem Bailey Power Park

In the center of the Innovation Quarter sets 1.6 acres of public green space. With a stage, patio, and large grassy area, Bailey Park is one of the best places to enjoy free community activities. From yoga, film screenings, and festivals, Bailey Park is an excellent place to find all the weekend action in Winston-Salem! 

Kaleideum North

Kaleideum North (previously SciWorks) boasts a lot of outdoor activities for the whole family. Whether it’s stargazing in the planetarium, strolling one of the many nature trails, or checking out the animals living in their habitats, there’s plenty for a young explorer to experience as well.

Children’s Museums in North Carolina

Winston-Salem Parks and Greenways

Things to Do in Winston-Salem NC Quarry Park Image
Quarry Park.

Winston-Salem is home to some fun outdoor places to explore, too. For a cool view of the city while still in a natural setting, check out Quarry Park. 

Muddy Creek Greenway and Salem Creek Greenway are two more options if you’d like a nice getaway while in Winston-Salem. On the parks’ side, we thoroughly enjoyed Washington Park, especially for the giant dinosaurs all over the playground. It’s another one of the many things to do in Winston-Salem for kids. 

Read More: Outdoor Activities in Winston-Salem

Where to Eat in Winston-Salem (Local Restaurants)

Sweet Potatoes

Restaurants in Winston-Salem NC Sweet Potatoes Image

If you’re looking for a restaurant in Winston-Salem that gives you everything you needed to know about the South, it would be Sweet Potatoes.

With her grandmother’s pan-fried chicken restaurant next door and utilizing the state vegetable in sweet and savory ways, Sweet Potatoes is a must-stop bite when in Winston-Salem.

Read More: Women-Owned Businesses in Winston-Salem

The Katharine

Even if you’re not staying at the Kimpton Cardinal, check out The Katharine. This incredible French Brasserie serves incredibly crafted meals with incredible attention to detail, which we share more about here. It would be a great addition to your list of romantic things to do in Winston-Salem.

Hotels in Winston-Salem NC The Katharine inside The Cardinal Hotel Image

Read More: Day Trips from Greensboro

Krankies Coffee

Krankies Coffee is a cool small-batch roastery and café with the perfect vibe to start your day. We sipped on our coffee and brunched hard before exploring the rest of Winston-Salem. Make sure to order their chicken biscuit with Texas Pete!

Many of our friends rave about Mozelle’s and Quanto Basta, too. If you’ve been to the area, what are your favorite restaurants in Winston-Salem?

If you’re having a hard time deciding, join a Taste Carolina Gourmet Food Tour for one of the most delicious things to do in Winston-Salem. 

Where to Drink NC Beer

North Carolina Breweries Foothills Brewery Image

If you want to dig into North Carolina beer, please explore the creations from Foothills Brewery! A visit here is certainly one of the best things to do in Winston-Salem.

We hear the burgers are gigantic and super juicy, too! Don’t get hung up on visiting the biggest of the breweries in Winston-Salem, as you have to check out Small Batch Beer Co. and at least Wise Man Brewing!

Things to Do in Winston-Salem’s Surroundings

Vineyards and Wineries

Exploring the 1.4 million-acre Yadkin Valley is one of the finest things to do in North Carolina. It’s just west of Winston-Salem and rich in vines!

If you head out there, you’ll find 40-plus vineyards and wineries to choose from. Many are featured among the best in North Carolina for good reason.

Surry County Wine Trail Pilot Mountain Vineyards

More than half of these wineries feature on the Surry County Wine Trail, in case you’re up for a challenge. Drink responsibly.

Our advice? Keep coming back and cross one off your list each visit! You can also hop on a North Carolina wine trail. Winston-Salem is in a good spot because it’s near a couple of them!

While we do the same, here are some other places you can check out for a wonderful day trip from Winston-Salem.

Hanging Rock State Park

Hanging Rock Trail Views from the Top
Nice viewpoint at Hanging Rock State Park.

30 miles north of Winston-Salem and you can find yourself trekking high about the clouds at Hanging Rock State Park. This 7,869-acre park’s trails are some of our favorites to hike in North Carolina.

However, you can also chill out by the water or on a boat, or camp out for a weekend. Our favorite trails are the Hanging Rock Trail, Cook’s Wall, and Moore’s Wall, but if you’re looking for a shorter hike there are plenty of waterfalls (one of the best in NC) or even boat rentals to paddle along the lake.

Read More: 20+ Kid-Friendly Waterfalls In NC (Easy Hikes And Swimming Holes!)

Pilot Mountain State Park

Pilot Mountain nc Image

Short on time but still want some fantastic views? Head north from Winston-Salem about 22 miles to Pilot Mountain State Park.

This geological feature in Surry County sticks out like a sore thumb! But the views are best from the top.

Drive up the winding road and look down on the beautiful sights of rural North Carolina. You may even catch sight of brave people scaling the side of the mountain’s steep cliffs!

What else is there to check out around Winston-Salem? We’d love to know more!

Read More: Colorful Fall Hikes in North Carolina (+ 20 Beautiful Places to Explore!)

Ready to Dig Into these Fun Things to Do in Winston-Salem?

While digging into these awesome things to do in Winston-Salem, one thing we realized is that this really is a city for everyone. Whether you’re a foodie, brew lover, oenophile, love the great outdoors, history buff, or a family, there really is a lot to fill your itinerary.

The city is perfect for a day-trip, a weekend getaway, or a long-term commitment. Personally, we see Winston-Salem as a great way to experience all that North Carolina has to offer.

Ever been to Winston-Salem? What did you think of it? What’s the first place you’d check out when in Winston-Salem? If we missed something, feel free to let us know about it.

More Things to Do in Winston-Salem

6 thoughts on “20+ of the Most Fun Things to Do in Winston-Salem (Great Food, Wonderful Hotels, and More!)”

  1. If you want a quick trip to a boutique vineyard, just 20 minutes from Downtown Winston-Salem is Cellar 4201. It’s beautiful and has some great wines. Wines are well made and worth the trip.

    Reply
  2. We love the art on the buildings in DADA, Kermits Hot Dogs, Reboot – an arcade with pinball, skee ball, old video games like Asteroids and Pac-Man nice stop for kids or adults and they serve beer…., love Bethabara Park, the old Shell gas station and a Saturday night stop at Bowman Gray Stadium – a NASCAR icon and an at least once-must-see for stock car racing…..I like that other than hiking, everything is close together.

    Reply
  3. Hanes Mall Blvd. Has everything for your shopping needs. From the classic mall to the big box stores to restaurants. One left and 2 blocks on Stratford there’s some local eateries or one left 2 blocks on Jonestown road is a huge used bookstore !

    Reply

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