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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.
Here are creative date ideas in Winston-Salem, whether it’s the first date or a special celebration!
Update March 2026
Picnic
Nothing says romance like a picnic! Buy a prepared meal from Buie’s Market, Washington Perk, or Acadia Foods, and spread out a blanket at a picturesque spot like Reynolda House’s front lawn, The Quarry at Grant Park, or Bailey Park.
- Bonus: Feeling extra fancy? Book a luxury picnic at The Little Chapel at Haven Ridge.
Arcade
Arcades are just as much fun as an adult! Take your date to one of the several in the Winston-Salem area, including Dive Bar, ROAR, Reboot, Camel City BBQ, and Village Square Arcade.
DIY
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! Shop at the Winston-Salem Fairgrounds Farmers Market, Cobblestone Farmers Market, or one of these other farmers markets. Choose fresh ingredients and make a delicious meal together!
Movies
Start your evening at one of 4th Street’s establishments, like Camino Bakery or Jeffrey Adams, then catch a movie at a/perture, Winston-Salem’s boutique movie theater!
- Bonus: 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! Spots 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 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.
- Bonus: Don’t forget about Art Crush! Several times through the year, the Arts District turns into an artist vendor market with live performances throughout the evening.
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.
Find when and where trivia and music bingo nights are happening using our weekly event guides!
Hiking
Explore the beauty of nature together! Winston-Salem is close to several great hiking spots, whether you’re looking for something casual or more challenging.
- Bonus: For a really special date, consider going on a sunrise hike!
Golf Simulators
Enjoy a game of golf any time of the year with golfing simulators at locations like ROAR and Whiskey, Taps, and Tails Saloon.
- Bonus: Is 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 to dance together! Take classes at one of several studios around town or join a pop-up class — discover your options in our dancing guide!
Get Creative in the Kitchen
Deepen your connection with a couple’s cooking class! For about the cost of a nice dinner out, you and your partner can learn a new skill, share a great meal, and enjoy the satisfaction of creating it together at Taste Buds Kitchen and Southern Home & Kitchen.
Seasonal
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? 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!
