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Date night ideas for every type of Twin City resident

Got a hot new fling? Hoping to spice things up with your longtime partner? We’re here to help plan your next date in Winston-Salem.

The outside of a brick building, with people sitting on long picnic tables under umbrellas.

A bike and a brew sounds like the perfect date to us.

Photo via @wisemanbeer

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Kids, this is the story of how I met your mother, and it was all thanks to WStoday.

Ok, so maybe that’s not exactly how the 2000s sitcom went, but if Ted Mosby had consulted us for date night ideas, we could’ve shaved the show down to two seasons (and saved his kids a lot of time). Regardless, whether you’ve met “the one” or are hoping to impress someone new, we’ve got 20+ local date night ideas that are legen — wait for it — dary.

For the ones who want a night out on the town

If the way to their heart is through their stomach

  • Take your date to easytalk by Ginger Fox Beverage (next to East of Texas + Lesser Known Beer Co.) for a unique cocktail experience — talk to the bartender for a minute, and they’ll serve up a cocktail catered to your tastes.
  • Make a meal together with a cooking class by Southern Home & Kitchen. The organization offers a variety of classes based on your preferences, from Italian dishes to the perfect flank steak.
  • Get all dressed up for dinner at one of Winston-Salem’s fancier dining options. We love Spring House Restaurant, Ryan’s Restaurant, Jeffrey Adams, and Mozelle’s.

If you love the great outdoors

  • Head to Bailey Park’s lower lawn to take in a movie under the stars (plus, drinks from Incendiary Brewing Co. and snacks from rotating food trucks). View the schedule of showings at the park to plan this date.
  • Pack a picnic and take a romantic evening paddle on Salem Lake with $4/hour kayak rentals from May through September.
  • Take in the sunset at The Quarry at Grant Park. Pro tip: Try going on a weekday — the quarry can get busy.
  • Grab a FLOW bike at one of the downtown stations and ride it to the bike dock by Wise Man Brewing, where you can cheers to a successful date night.

For the ones who like to play games (just not with your heart)

  • Grab a drink and play to your heart’s content at Reboot Arcade Bar. Up the ante by making a bet with your date — whoever wins the Skee-Ball or Pac-Man tournament buys drinks.
  • Roar is the perfect place to bring your picky eating date, thanks to the food hall with plenty of options. After eating, head to the mini bowling alley or The Twisted Putter for interactive mini golf.
  • Grab some barbecue at Camel City BBQ Factory and play a round of cornhole on the upper deck, or enjoy a few games in the upstairs arcade.

If you’re really hoping that it works out

  • Climb their list of best dates with a trip to Firsthand Climbing.
  • Take a dance class together at Best of Ballroom Dance Studio. Choose from classes like West Coast Swing, Foxtrot, and Tango.
  • Join Lotus Yoga’s yoga + run club on Thursday nights for $8. Don’t worry if you two aren’t experienced runners — walkers are more than welcome.

If you want an “old fashioned”-style date

  • Split a milkshake or an ice cream sundae at Mayberry Ice Cream for old-school diner vibes.
  • Make the drive to nearby Mount Airy (the inspiration for The Andy Griffith Show’s setting) and stroll down Main Street hand-in-hand before stopping by Walker’s Soda Fountain.
  • Chat over an actual Old Fashioned at Joyner’s. Bonus: Head to the 70s-inspired room in the back for more old fashioned flair.

If you wanna show off by knowing all the hottest events in town

  • Shameless plug: Sign up for our daily newsletter, where we call out our top picks of things to do around town. Your date doesn’t have to know we’re behind it, you can take all the credit.
  • Stay up-to-date on the coolest local events around Winston-Salem with our events page.
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