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Date night ideas for every type of Winstonian

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

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

Table of Contents

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

  • See an indie film or documentary at a/perture cinema and stop in Camino Bakery across the street for dessert. Bonus: you can bring your vegan date here, too.
  • Head to the Coalpit for live music (check dates before you go), plus a beer from Incendiary and a slice of pizza from Cugino Forno.
  • Set the stage for romance by checking out a theater production from talented local actors.
  • Hire a pedicab and cruise around downtown. You’ll see spots you can wander to after your tour.
  • Explore Industry Hill and visit breweries and bars on 9th Street. Taste craft beers from Radar and Wise Man, then end up at The Ramkat for a live show or see who’s performing on the stage at Earl’s.

If the way to their heart is through their stomach

If you love the great outdoors

  • Head to Bailey Park’s lower lawn to take in a movie under the stars (plus, drinks from Dram & Draught 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. Bring a lock to memorialize your love on the overlook.
    WStoday_Cityscape from Quarry at Grant Park_Sarah H.

    “Cityscape from Quarry at Grant Park”

    Photo by Sarah H. (one of our 2023 Picture of the Year finalists)

  • Walk through Reynolda Gardens and admire the lush landscape. It’s open to the public dawn to dusk year-round.
  • Take a mural tour and admire the creativity around Twin City streets. Print out a walking map before you go and plan your route. We suggest ending up at ARTivity on the Green on North Liberty Street and watching the sunset over the city skyline.

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.
    Dark room with neon colored games. A group of three people is crowded around two separate games.

    Love might not be a game but it doesn’t mean you can’t have fun.

    Photo courtesy of ROAR/Mayfair Hospitality

  • 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.
  • Head to Dive Bar for some friendly competition on arcade games or serenade your date with karaoke on Tuesdays.

If you’re really hoping that it works out

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.
Road lined with brick buildings and trees.

Main Street in Old Salem is perfect for a romantic stroll.

Photo by WStoday

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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