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Creative Date Ideas in Winston-Salem

You swiped right, stumbled upon each other at a cozy coffee shop, or got playfully set up by that friend who thinks they’re a matchmaker. Now it’s time to plan the perfect date.

While sharing a meal is nice, here are some creative date ideas in Winston-Salem whether it’s the first date, the tenth date, or a special celebration!

Update May 2024


Creative Date Ideas in Winston-Salem
Picnic at The Little Chapel at Haven Ridge



Nothing says romance like a picnic! Buy a prepared meal from Buie’s Market, Theodore’s, Washington Perk, or Acadia Foods, and spread out a blanket at a picturesque spot like Reynolda House’s front lawn or Bailey Park. 

Feeling extra fancy? Book a luxury picnic at The Little Chapel at Haven Ridge.



Arcades are just as much fun as an adult! Take your date to one of the several in Winston-Salem, including Dive Bar, ROAR, Reboot, and Camel City BBQ.



Looking for something creative? Try decorating a cake together at The Canvas Cake Studio, creating something unique at Mixxer, or sipping wine while painting at Wine & Design. Check out our DIY guide for even more DIY ideas in Winston-Salem!


Rent Bikes

Do you both love outdoor activities? Rent bikes from Triad Eco Adventures and ride along Salem Creek Greenway, the Salem Lake Loop, or Long Branch Trail. If you’re feeling particularly adventurous (or want to extend your time together), you can combine all three trails into one long bike ride.


Farmers Market

Make “eating in” a special occasion! Browse the Fairgrounds Farmers Market, Cobblestone Farmers Market, or one of these other farmers markets together. Choose fresh ingredients and make a delicious meal together.



A classic date idea! Check out a/perture, a boutique movie theatre downtown. Before or after the movie, grab a small bite at Camino Bakery or enjoy a meal at Xcaret Mexican Grill.

Prefer to be outside? There are dozens of outdoor movies happening this summer!


Live Music

Take your date to a local bar or brewery for a drink and live music! Businesses like Wise Man Brewing, Joymongers Barrel Hall, and Foothills Tasting Room always have a local musician performing on weekends, and our live music guide is updated weekly so you always know who’s in town.


Art Galleries & Museums

Explore the art galleries and museums in Winston-Salem together! Learn about our city’s earliest European settlers at Old Salem Museum & Gardens, marvel at the art exhibitions at SECCA, or enjoy a blend of history and art at the Reynolda House Museum of American Art. Check out our museum guide for even more options.

Also, don’t forget about Art Crush! Every third Friday from April to December, the Arts District turns into an artist vendor market with live performances throughout the evening. It’s a memorable artistic experience!


Trivia & Music Bingo

Just getting to know each other? Keep it casual with a trivia or music bingo night at one of the local bars or breweries like Incendiary Brewing, Fiddlin’ Fish, or Little Brother Kernersville.

Our weekly event guides can help you determine when trivia and music bingo nights are happening at local establishments!


Golf Simulators

Enjoy a game of golf any time of the year with golfing simulators at locations like ROAR and The Playground.

Mini golf more your thing? The Twisted Putter at ROAR features digitized scoring and custom light and sound effects for a unique experience.


Dance Lessons

Learn how to dance together! Several studios in town offer classes, such as Best of Ballroom Dance Studios and Real World Ballroom.

If you enjoy dancing outside a studio setting, SonCaribe Latin Dance offers classes at Art For Art’s Sake and Incendiary Brewing. Megalina also offers Latin dance classes at East of Texas and Alma.



Plan your date around seasonal activities!

In North Carolina’s breathtaking spring, take that special someone to pick flowers or fill up a basket with farm-fresh strawberries.

During summertime, go blueberry picking or cool off at one of these nearby waterfalls, lakes, and rivers.

Once the leaves start changing in fall, visit a pumpkin patch or go apple-picking at one of the nearby farms. Like a good scare? Near Halloween, enter a haunted attraction if you dare!

When the weather turns chilly in winter, go ice skating at the Winston-Salem Fairgrounds or take a day trip to one of these great spots for skiing, snowboarding, or tubing.


Want even more ideas? Subscribe to our newsletter to see what’s happening in Winston-Salem every week!


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