When we told our North Carolina friends we were going to spend 3 days in Winston Salem they asked why? According to them, there weren’t many things to do in Winston Salem or see. As always we like to go into a city with no expectations and judge based on our travel experience.

Winston Salem surprised the heck out of us, there were a ton of things to do in Winston Salem, the food was amazing, and we loved the Southern hospitality. After our trip to Winston Salem, we convinced our North Carolina friends to give it a second shot and we gave them this list of fun things to do in Winston Salem

13 Fun Things To Do In Winston Salem

1. Old Salem Museums & Garden

One of the city’s most famous tourist attractions is the historic district of Old Salem. Founded in 1766 Old Salem was formed by members of the Monrovian church. Old Salem Historic District was declared a National Historic Landmark in 1966. Old Salem shows the Moravian Culture back in the 18th and 19th centuries complete with houses, shops, taverns, churches, etc.

Admission: $18 entrance to 2 museum buildings $27 entrance to all buildings, students half price
Address: 900 Old Salem Road Salem, NC

2. Ride A Segway With Triad Eco Adventures

We’ve seen Segway tours around the world but never been on one til Winston Salem. We went with Triad Eco Adventures on their Old Salem tour. After a safety video and a “drivers test” we hit the road on our Segways. They offer tons of different Segway tours from Mayhem & Mystery, Glide & Dine, Public Arts, and more. We covered so much on our totally Salem Segway Tour, there is no way we would have seen as much on a traditional walking tour. Segways are awesome and so easy we definitely will be taking other Segway tours around the world.

Prices: $64 for 2-hour Segway Tour
Address: 176 YWCA Way Winston Salem, NC

3. Find an Art-o-mat Machine

When cigarette machines were banned in 1997 Winston Salem local artist Clark Whittington had the idea to dispense art from them. He made the first Art-o-mat machine and showed it at a local cafe art show but the owner loved it so much she wanted it to stay. That is when the idea to produce more begin, originally the art was photos from Clark on wooden blocks for $1 but he has since sourced artists around the world to keep them stocked. There are now over 100 Art-o-mat machines around the USA with even one in Austria and one in Australia. Check here to see if there is an Art-o-mat near you.

Price: $5 cash only
18 Locations in Winston Salem: Mary’s Diner has the original Art-o-mat at 723 Trade St NW

4. Brewery Tour At Foothills Brewery

There are several Breweries in Winston Salem but our personal favorite is Foothills Brewery. They started brewing beer in 2005 and have become a local favorite. Their most sought-after beer is their Sexual Chocolate an Imperial Stout, people camp out in line for its release. There are so many people in line there is an officer on site to keep the line in order. If you ever see Sexual Chocolate on the menu order it!

Admission: Free
Brewery & Tasting Room Address: 3800 Kimwell Dr. Winston-Salem, NC
Downtown Brewpub Address: 638 West Fourth St. Winston-Salem

5. Pilot Mountain

Worth a little road trip is Pilot Mountain State Park which located 25 minutes outside of Winston Salem. Pilot Mountain rose out of the ground from nowhere and stands at more than 2,000 feet. There are great hiking trails, camping, and epic views. You can see the Blue Ridge Mountains, Sauratown Mountains, and the Yadkin Valley from high on top of Pilot Mountain.

Admission: Free
Address: 1792 Pilot Knob Park Road, Pinnacle North Carolina

6. Wine Tasting in the Yadkin Valley

The Winston Salem area is known for growing tobacco but when the tobacco economy changed several farmers took to wine-making. The Yadkin Valley is great for Muscadine and Scuppernong grapes. There are 45+ wineries in the Yadkin Valley to visit so you might want to get a wine trail map and visit those with your favorite wines. Our favorite winery was the Elkin Creek Vineyard not only was the wine great but we loved the little creek running behind the vineyard. If you aren’t a wine lover several of the wineries also brew their own beer like Round Peak, so beer lover’s can enjoy a beverage too.

Address: Yadkin Valley to Winston Salem is roughly 45 minutes

7. Visit the Southeastern Center for Contemporary Art

If you like contemporary art this is the best place to see the emerging art scene in Winston Salem, it’s also known as SECCA. They showcase work of local artists as well as national and international artists. When visited they had the 20-year Art-o-mat exhibit where we got to meet the local artist Clark Whittington, was great chatting with him how his idea has evolved over 20 years. Click here to check out what exhibit is currently being displayed.

Admission: FREE
Address: 750 Marguerite Dr, Winston Salem, NC

8. Explore Downtown Trade Street

One of my favorite things to do in Winston Salem was to walk out of our hotel the Historic Brookstown Inn. Our hotel was only a mile from Trade Street which had a bunch of restaurants and shops in the art district of town. We highly suggest having lunch or dinner at Sweet Potatoes located right on Trade Street, it’s a must for sweet potato lovers.

Related Article: Best Restaurants in Winston Salem

9. ARTivity on the Green

Located right behind Trade Street is ARTivity On The Green a half-acre public art park. When you’re in downtown Winston Salem and see a red line just follow that and it will lead you to ARTivity. There is a wall with street art, steel ribbons which offer shelter for artists, and a grassy area to chill.

Cost: Free
Address: 630 N Liberty St, Winston-Salem, NC

10. Winston Cup Museum

An easy walk from Trade Street is the Winston Cup Museum.Learn about stock car racing during the Winston Cup Series of NASCAR. Not only are exhibits and history but a ton of race cars on display drive by Dale Earnhardt ST, Wendell Scott, and Alan Kulwicki. The Winston Cup Museum is one of the most popular things to do in Winston Salem with young boys and adults too.

Price: $8 adults, $4 children ages 5-12, and under 5 free
Address: 1355 N. Martin Luther King, Jr. Drive Winston Salem, NC

11. Reynolda House

The Reynolda House house was originally the home of the tobacco tycoon R.J Reynolds but is now an art museum with one of the country’s best collection of American paintings. The house was built in 1917 on the 1,067-acre estate where R.J Reynolds and his family lived and in 1967 it was opened to the public as an art museum. We visited the Reynolda House on the opening day of the Georgia O’Keefe exhibit which will be on display for 3 months for the exhibit lineup click here.

Price: $22 adults, children under 18 and students FREE
Address: 2250 Reynolda Road Winston-Salem, NC

12. Squad car tour in Mount Airy

Technically this isn’t in Winston Salem but it definitely is worth the 40-minute trip. If you’ve ever seen an episode of Andy Griffth it’ll be like being on the set. Mount Airy is the town that inspired Mayberry on The Andy Griffth ShowThe squad car tour takes about 30 minutes and our guide gave us a great history of Andy’s life growing up and all the Mount Airy references in the show. We stopped at Andy Griffith’s childhood home where you can actually spend the night (owned by Hampton Inn), click here to check rates and availability.

Price: $35 for the entire car 5 people or less
Address: 625 S. Main St. Mt Airy, NC

13. Unique Place to Stay Graylyn Estate

If you’re looking to stay somewhere that isn’t a chain hotel and has some history and charm head to the Graylyn Estate. The Graylyn Estate is a 55-acre property located a few minutes from downtown Winston Salem has nearly 60 rooms and 46,000 square feet. When booking a room request if you want one the updated rooms (which are gorgeous) or one of the older historic ones. Even if you don’t stay the night it’s worth stopping for a meal in one of the restaurants of the free lemonade and cookies they offer every afternoon 3-5pm.

Price: $175+ a night, click here for rates
Address: 900 Reynolda Road Winston Salem, NC

13 Fun Things to do in Winston Salem North Carolina