Whether you’re going out with someone new or having a date night with your hubby / wifey, planning a fun date night can be frustrating. You may be drawn to do the same things over and over again because you don’t know what else there is to do! Hopefully you get some new ideas every month on our blog with our What's Happening posts, but these date ideas are always a great choice! So, go on. Put yourself out there. And get out on the town!
(Hey, what do bloggers know about dating, anyway? We're glad you asked!)
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Great for first dates, keeping it casual, or catching up, the coffee date is classic for any couple. And Winston-Salem boasts an impressive selection of coffee—trust us, we know coffee!
Many of these coffee houses also feature dessert, beer, and wine, making this a perfect choice for morning, afternoon, or evening dates, and each is within walking distance of many of the other spots on our list!
Twin City Hive301 Brookstown Ave #300 | Winston-Salem, NC 27101
Artsy, slightly industrial but cozy and warm. Twin City Hive is located by the Brookstown shops, which include the Wag Boutique (see Dog-Friendly Date below!) Their menu features pastries, truffles, and gluten-free options! We’re practically addicted to TCH. Like bees to honey—what more can we say?
Footnote Cafe & Bar634 W 4th St ste 120, Winston-Salem, NC 27101
One of the newest additions to the Winston-Salem coffee scene, Footnote is connected to both the Bookmarks bookstore and Foothills Brewing (via their taps). It’s a great quiet spot to sit and read after browsing the shelves, or sip with someone special! (Also, it has the perfect name—major marketing/branding props to you, Footnote crew 💕).
Camino Bakery310 W 4th St | Winston-Salem, NC 27101
Located across the street from a/perture Cinema (see Movie Dates below), Camino features an impressive selection of baked goods, coffee, wine, and more. It’s a popular choice for many— and a favorite study spot for students—giving it a hip, creative vibe. A great choice for the late afternoon or evening, or if you’d like to sit outside!
211 E 3rd St, Winston-Salem, NC 27101
A Winston-Salem staple, Krankies is literally the FIRST place my wife and I visited when we came to the city for the first time. It’s changed a lot over the years (#glowup) without sacrificing its commitment to local culture (check out the WhereHouse Art Hotel, located upstairs—see Artsy Date Night below!) They now feature an extensive menu and a full bar.
Bonus: date night at home!
Buy a bag of Krankies coffee to brew at your convenience and pair it with a homemade breakfast or with some sweets to-go (or delivered via Takeout Central / Uber Eats if you’re feeling especially decadent!)
Another traditional option, with a fun twist. These are more than your average night at the movies!
A/perture Cinema311 W 4th St, Winston-Salem, NC 27101
Conveniently located at the heart of 4th st, a/perture is Winston-Salem’s non-profit arthouse theater, and we are so lucky to have them! Offering a wonderful selection of independent, documentary, foreign, local, and festival films, it’s a great way to broaden your horizons, or catch that critically-acclaimed movie you can’t find anywhere else. They also offer beer and wine, healthy snacks, and traditional-style popcorn!
$3 Movie Theater2095 Peters Creek Pkwy, Winston-Salem, NC 27127
Ok, ok, so it’s actually called Marketplace Cinemas, but aka (affectionately known as) the $3 Movie Theater, where you can two tickets + popcorn / drinks / candy for under $10. And their movie selection is great—often screening titles that you probably just barely missed in the other theaters around town.
Cinema Under the StarsIf you’re like me, you like to take advantage of anything you can do outdoors while it’s warm, but not too warm, like a nice summer evening. If that’s the case, then you’ll enjoy lounging on a picnic blanket with your loved one and soaking in the nostalgia of one of your favorite movies. During the summer months, there are plenty of opportunities to see these movies at venues such as the Reynolda House Museum, Bailey Park, and local churches.
An essential part of any date is the meal you share, whether it’s a full four courses, some light tapas, or just dessert. Honestly, there is so much amazing food in Winston, it’s impossible to choose (I’m starting to sweat just thinking about it… and drooling). So this list is just to give you a taste of our favorites.
Sushi, Asian, etc.
- HakkaChow (amazing Asian fusion. Sunday Sushi Special = buy one, get one ½ price)
- The Basil Leaf Thai & Sushi (right near Hakka Chow, also amazing)
- Kimono (various locations, my favorite for sushi)
Arts District / Trade Street
- Finnigan’s Wake (Irish Pub, great bar)
- Sweet Potatoes (Southern/ soul food / incredible)
- Senior Bravo In & Out (Mexican / casual / muy delicioso)
- 6th & Vine (eclectic, great patio, ½ price wine every Thursday, ½ bottles every Sunday!)
4th St Favorites
- Quanto Basta (upscale but laid-back, great wine list)
- Foothills Brewpub (great beer, great food, can’t go wrong)
- 4th Street Filling Station (great drink specials throughout the week, Sunday brunch)
- Meridian (excellent fine dining, special occasion)
- The Quiet Pint (great to watch a game, diverse menu, great drinks)
- Cin Cin Burger Bar (fun speakeasy theme, cocktails, great burgers)
- The Porch (excellent cantina menu. Try their zucchini quinoa burger!)
Winston-Salem is increasingly friendly to our furry, four-legged family members. And if you love taking them out on dates (because they’re the best judge of potential partners), we’ve got some great ideas!
Wag Boutique is basically the Twin City Hive for your dog (which makes sense—it’s located right next door!) Stop in to grab a bag of food, some treats, and a toy for the dog park! Or just browse and see what heaven on earth looks like for your pup!
Washington Dog Park or Horizons ParkDepending on whether you want to stay close to central Winston or head up North, you can visit either off-leash dog parks in Winston-Salem. The Washington Dog Park is in central Winston-Salem and offers a gated area where you can let your pup run free and socialize with others while you spend time with your spouse or date.
Horizons Happy Hounds Dog Park might be the better option for people with smaller dogs, since they have a specific area for them. This park also has water spigots, plenty of shade, and benches for you! Either way, get to the park before sunset and let your dogs burn some energy while you chat.
Hiking / Walking TrailsOf course, Winston also has plenty of walking trails and nearby hiking that make for a great date for both your partner and your pup! You’re likely to encounter many others doing the same!
For walking trails:
- Reynolda Village Nature Trail
- Bethabara Historic Park
- Salem Lake
- Tanglewood Park (check out their annual holiday event “Paws in the Park”)
Bonus: date night at home!
Foster the love and foster a furry friend from the Forsyth Humane Society or other local rescues! Whether it's two week or longer, supplies are provided (there's no fee to foster). Best of all, you'll help keep shelter space open for other homeless pets!
Winston-Salem is known as the city of the arts, and for a good reason! Between our eclectic local and regional artists to world-renowned exhibitions, there’s plenty to see, whether you and your date are fine art aficionados or more casual connoisseurs.
Southeastern Center for Contemporary Art
750 Marguerite Dr, Winston-Salem, NC 27106
A must-see for any fan of contemporary art, SECCA features an impressive array of American and international artists throughout its sprawling halls and gallery space. Check out a gallery opening or one of their artist talks, and then grab some dinner at one of the excellent restaurants located nearby, including Fratellis Steakhouse and Reynolda Village!
Reynolda House Museum
2250 Reynolda Rd, Winston-Salem, NC 27106
Just down the road from SECCA, the Reynolda House Museum is another essential arts destination. Located in the restored 1917 mansion of R. J. Reynolds, this museum features some of the most well-known American artists, such as Georgia O’Keeffe and Dorothea Lange, and brings together history, culture, and kid-friendly events.
Arts District on Trade St
Whether you’re bar hopping or walking off your delicious dinner from Finnegan’s or 6th & Vine, you can stop in to the many galleries down Trade Street in the Arts District. This includes Red Dog Gallery, Artworks Gallery, Fiber Company, Piedmont Craftsmen, The Other Half, Delurk Gallery, Ember Gallery, and many more! There’s also a Gallery Hop on the first Friday of every month!While you’re out and about, be sure to stroll through Artivity on the Green, just behind Single Brothers, featuring an innovative design by Stitch Design Shop, a rotating selection of work by local artists, and occasional concerts!
The WhereHouse Art Hotel
211 E 3rd St, Winston-Salem, NC 27101 (upstairs from Krankies)
Whether you’re on vacation or a staycation, the WhereHouse Art Hotel is cooler than virtually any other AirBnB you’ll find. Bohemian, contemporary, and occasionally strange, each room is a gallery space of its own. It’s also open to the public for events, such as stairwell concerts and other experimental exhibitions! Always worth checking out!
Bonus date: take an art class together!
The Sawtooth School of Visual Arts is a great way to foster or develop your talents, whether you try watercolor, pottery & ceramics, photography, jewelry making or something else!
Have we saved the best for last? As with dining, Winston has almost too many awesome bars to choose from. That’s why we’re suggesting a bar hop. With so many of these places within walking distance from one another, it’s easy to visit several in an evening out on the town.
Looking for the hippest hole in the wall where you’ll find exciting cocktails and interesting folks? These eclectic bars have lots to offer, such as live jazz every Tuesday at Tate’s Craft Cocktails & every Saturday at Carolina Vineyards & Hops!
Single Brothers is great when you’re on Trade St and want to sit outside, while The Katharine Brasserie & Bar is great for more upscale occasions. Looking for a bourbon bar? Try The Trophy Room!
Make your way down Burke Street and stop by the comics store, grab a drink at Old Winston Social Club. End up at Gatsby’s Pub for karaoke (hosted on Saturdays), and round it out with a late-night slice or two from Burke Street Pizza!
It might be difficult to draw the line between bars, breweries (see below), and tasting rooms, but for the sake of discussion, let’s say these are in a category of their own. Juggheads is always fun for their tap takeovers, catching a game, sampling a cigar, playing board games / arcade games, or filling a growler. (Speaking of which, check out The Beer Growler—it’s even better paired with takeout from Mr. Lu’s right next door!) The Foothills Tasting Room is also a solid choice, especially with takeout from The Greek Guys!
BreweriesThe beer scene has been blowing up in recent years, and we can’t wait to see what the future holds! Winston is quickly becoming a destination city for beer lovers, and these bars are essential stops for fun date nights, double dates, enjoying food trucks & seeing some live music:
Go Wine Tasting!Just outside of Winston, you’ll find the Yadkin Valley, home to some world-class wineries and romantic vineyards! The team at Nu loves Raylen for their wine, their fun events, and their gorgeous, sprawling landscape. (They’re also an awesome wedding venue, but maybe save that discussion for, like, your third date or something?)
Divine Llama Vineyards is always fun for dates. Share a bottle of wine and wander the farmland, admiring their dogs, miniature horses, and llamas (of course!) Jolo Vineyards offers another scenic view, just below Pilot Mountain, with great outdoor seating and an upscale atmosphere.