The Best Things to Do in Winston-Salem this Summer

7 minute read

Cyclists pass by Bailey Power Plant during the 2021 WInston-Salem Cycling Classic race.

There’s no beach or mountain within Winston-Salem’s city limits, but that doesn’t mean our city isn’t a destination for summer fun. Whether you’re planning a staycation or are looking to get to know the city a little bit better, there are plenty of activities and events to keep you entertained this summer.

Cobblestone Farmers Market

Cobblestone Farmers Market is a popular Saturday morning stop for many year-round, but the market “doors” are also open on Wednesdays from 4:00 – 6:00 pm during the summer. Featuring a variety of vendors from northwest North Carolina and Southern Virginia, most of the food and goods offered have traveled 60 miles or less to get to Cobblestone.

Along with fresh produce, meats and flowers, you’ll find goat cheese from Buffalo Creek Farm and Creamery, honey from Lil Sarah’s Bee Farm, fruit preserves from Piedmont Provisions and more. Cobblestone has a lineup of vendors making weekly appearances but also invites seasonal vendors to participate, making every market experience different. Make plans to arrive early, browse the booths, and get inspired for your next meal.

Tomatoes from a vendor at Cobblestone Farmers Market.
A vendor at Cobblestone Farmers Market holds up strawberries for sale.

Images from Cobblestone Farmers Market Instagram

  • The Cobblestone Farmers Market is located at: 1007 S. Marshall Street, Winston-Salem, NC 27101
  • Saturdays 8:30 am – 12:00 pm (year-round); Wednesdays 4:00 – 6:00 pm (May through August)

Winston-Salem Dash

Rumored to be named for the hyphen in Winston-Salem, the Winston-Salem Dash is truly a hometown team. From their earliest days playing as the Winston-Salem Twins to their stint as the Warthogs playing at Ernie Shore Field, the Dash have held a place in Winston-Salem sports-lovers hearts since 1905.

The Dash is a High-A class minor league baseball team affiliated with the Chicago White Sox. Their home field, Truist Stadium, is located downtown in the perfect location for a summer night out. Almost every home game features a fun promotion—think a free Kids Zone, discounted beer or wine, and fireworks. The regular season ends September 11, so there’s still plenty of time to catch a game this summer.

A Winston-Salem Dash baseball player hits a pitch during a game.
The sun sets over a Winston-Salem Dash game at Truist Park in Winston-Salem.

Images from the Winston-Salem Dash Instagram

  • The Dash play at: Truist Stadium, 951 Ballpark Way, Winston-Salem, NC 27101
  • Visit their website for the full schedule and to purchase tickets

Winston-Salem Open Tennis Tournament

It’s fitting that John Isner, a Greensboro native, won the first Winston-Salem Open tennis tournament title in 2011. He successfully defended his title in 2012, but since then, a new champion has been crowned each year.

The Winston-Salem Open is part of the American Tennis Professionals (ATP) World Tour 250 Event Series. Held at the Wake Forest University Tennis Complex, the week-long tournament has brought big names and world-class tennis to Winston-Salem. Tickets start at $10 and are on sale now.

An aerial shot of a tennis match played at the Winston-Salem Open tennis tournament.
A tennis player serves the ball during a Winston-Salem Open tennis match.

Images from the Winston-Salem Open Instagram

  • The Winston-Salem Open is held at: Wake Forest University Tennis Complex, 100 West 32nd Street, Winston-Salem, NC 27105
  • August 20-27, 2022
  • Visit their website for the full schedule and to purchase tickets

Gears and Guitars

Known as “The Biggest Party on Two Wheels,” Gears and Guitars transforms downtown Winston-Salem for one weekend in September. Cyclists, enthusiasts and the cycling-curious come out in droves each year for this event. With food trucks and free live music throughout the weekend, the Gears and Guitars event certainly lives up to its nickname.

This year’s cycling includes a drag race-style event, a full day of amateur and professional criterium racing (a multi-lap race through city streets), and plenty of community rides. Saturday’s Winston-Salem Classic “crit” race through the Innovation Quarter is known throughout the cycling community as one of the most challenging courses on the circuit.

All events are free this year—including the concerts featuring Dawes, Tonic and Better Than Ezra (to name a few). Come early to stake out your spot, or opt for a VIP package to ensure you get the best seat in Bailey Park.

Professional cyclists riding through the Innovation Quarter during the Winston-Salem Cycling Classic crit race.
Concert-goers sit on the lawn in Bailey Park, waiting for the Gears and Guitars concert to begin.
  • Gears and Guitars is held at: Bailey Park and various locations throughout downtown Winston-Salem
  • September 9-11, 2022

Old Salem Historic District

If you want to explore the town’s history, there’s no better place than Old Salem Museums & Gardens. Since the 1950s, Old Salem’s staff and community volunteers have worked to preserve and restore Salem. Today, we see a reflection of the town’s rich and diverse cultural history of the early South—emphasizing the Moravians, enslaved and free people of African descent, and Indigenous peoples of the Southern Woodland.

A visit to Old Salem can be a leisurely walk through Main Street, the historic gardens and cemeteries. Consider purchasing tickets to the Museum of Early Southern Decorative Arts (MESDA) galleries to explore more history, art and culture. No matter how you spend your day, follow your nose to Winkler Bakery for a sweet treat.

A blueberry loaf cake from Winkler's Bakery in Old Salem.
A woman tends to the flax garden at Old Salem Museum and Gardens in downtown Winston-Salem.

Images from the Old Salem Museums & Gardens Instagram

  • Old Salem Museums and Gardens Historic District is located at: 600 South Main Street, Winston-Salem, NC 27101
  • Open year-round except for January; some venues are ticketed and have posted hours

Reynolda House and Gardens

It took Katharine Smith Reynolds and her husband R.J. Reynolds, founder of the R.J. Reynolds Tobacco Company, five years to build their sprawling 1,067-acre estate in the 1910s. Today, the 170-acre site is a one-stop-shop for many, comprised of the Reynolda House Museum of American Art, Reynolda Gardens and Reynolda Village Shops and Restaurants.

You can explore most of Reynolda by foot. Parking and Reynolda Gardens are free, but the museum may require a paid ticket. (Visit the Reynolda website to see if you qualify for free museum admission.) You’ll find more than 6,000 historical objects and a collection of world-renowned American art inside the museum.

If you’ve got time, stretch your legs through the Formal Gardens or along the wooded trails that meander around the estate’s perimeter. You’ll enjoy the many scenery changes, from wetlands to an expansive meadow to a waterfall. Once you’ve worked up an appetite, there are plenty of places to refuel at Reynolda Village—everything from donuts to dumplings.

The waterfall and bridge at the Reynolda Village walking trails.
The inside of Reynolda House Museum.

Images from the Reynolda Village and Reynolda House Instagrams

  • The Reynolda House is located at: 2250 Reynolda Road, Winston-Salem, NC 27106
  • Musem, garden, shops, and restaurants hours will vary

Coalpit Live Music Series

We promise a place named the “Coalpit” isn’t all dirt and grime. In fact, Winston-Salem’s Coalpit has become a popular hangout for friends, family and coworkers. Located in the Innovation Quarter, this open area was once coal storage for the coal-fired plants that powered nearby tobacco factories.

An evening enjoying the Coalpit Live music series is a perfect way to beat the summer heat. Upcoming shows include The Connells with Dawn Landes and an Independence Day Jam featuring local cover bands. With tacos from Alma Mexicana, pizza from Cugino Forno, beer from Incendiary Brewing, and gelato from Black Mountain Chocolate within sight of the Coalpit, you should be on track for a night of fun.

Crowds gather at the Coal Pit Live concert held in the Innovation Quarter's coal pit.
A musician plays the harmonica on stage during the Coal Pit Live concert.

Images from the Coalpit Live Instagram

  • The Coalpit is located behind Bailey Power Plant: 486 N Patterson Ave, Winston-Salem, NC 27101
  • See the Coalpit Live Facebook for more event information

There’s More to Explore in Winston-Salem

We know we can’t possibly list everything there is to do this summer in Winston-Salem, but this should give you a start. There are many more neighborhoods to explore, events to RSVP for and restaurants to try. No matter your summer plans, we encourage you to get out and experience more of what Winston-Salem has to offer.