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

Take your date to easytalk (next to East of Texas + Lesser Known Beer Co.) for a unique and intimate 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 at Southern Home & Kitchen. The shop offers a variety of classes so you can make a meal for two.
Get all dressed up for dinner at one of Winston-Salem's fancier dining options. We love Spring House Restaurant, Kitchen and Bar, Ryan's Restaurant, The Downtown Grille, Sage & Salt Bistro, and Mozelle's.

Grab a glass of wine and to share some small bites on the patio at 6th and Vine or from the window seats at Little Pep.
End the date with a sweet note by splitting a milkshake or an ice cream sundae at one of these ice cream spots in the Twin City.

Champagne and chocolates are just one way to celebrate. | Photo courtesy of The Graylyn Estate

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.

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.

Have you seen the muralists' work at the back of ARTivity on the Green? | Photo by WStoday

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.
It's all fair when it comes to love and war at ROAR as you tackle mini bowling 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.
Head to Dive Bar for some friendly competition on arcade games or serenade your date with karaoke on Tuesdays.

Love might not be a game, but it doesn't mean you can't have fun. | Photo courtesy of ROAR/Mayfair Hospitality

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.
Take a class together at Sawtooth School for Visual Art. You can learn to photograph, paint, or draw your significant other.

If you want an “old fashioned”-style date

Take a behind-the-scenes tour of how award-winning spirits are made here in Winston-Salem by taking a tour of Broad Branch Distillery or get cozy in the intimate setting of The Trophy Room — this speakeasy has personalized lockers so you can seal your love forever.
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.

Walk down Main Street in Old Salem and admire the centuries-old buildings. Stop by Lot 63 Coffee and Taproom for a beer or pop in Muddy Creek Cafe & Listening Room next door — musicians sometimes take the stage for live shows.

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.