Let’s be real—coming up with fresh date ideas in Winston-Salem isn’t always easy. Whether you’re planning a first date and want to make a great impression, or you’ve been with your person for years and want to break out of the dinner-and-a-movie rut, Winston-Salem has you covered.
This city has low-key gems, creative adventures, cozy corners, and even a llama or two (yes, really). Whether you’re a romantic at heart, a laid-back couple, or total goofballs who just want to laugh together—this list has something you’re going to love. And hey, we even threw in a few ideas outside the city that are totally worth the drive.
So grab your partner’s hand (or send them this post as a hint 😏) and let’s find your next perfect date idea.
Best Date Ideas in Winston-Salem (You’re going to love this!)
1. Stroll Through Reynolda Gardens
If you’re looking for a date that’s peaceful, pretty, and doesn’t cost a thing, Reynolda Gardens is such a vibe. I’m talking winding garden paths, colorful blooms that change with the seasons, and quiet little corners where you can actually hear the birds (yes, even in the middle of the city).
No matter if it’s your first date or you’ve been together for ten years, there’s something really sweet about walking side by side and stopping to admire the flowers. When it comes to Date Ideas in Winston-Salem, this spot definitely deserves a place on your list. Pack a light picnic, find a shady spot on the lawn, and you’ve got yourself a low-key, high-impact date.
Pro tip: Go during the golden hour. The way the light filters through the trees makes the whole place feel like a scene from a rom-com.
- Pros: Free, beautiful year-round, peaceful and personal.
- Cons: Limited seating if you’re planning a full picnic—bring a blanket just in case.
2. Wine Tasting at Childress Vineyards
Let me tell you—if you’ve never done a wine tasting at Childress Vineyards, you’re seriously missing out on one of the most romantic day trips near Winston-Salem. It’s just a 35-minute drive to Lexington, but it feels like you’ve escaped to wine country. The views are wide open and dreamy, with rows of vines stretching across rolling hills. It’s the kind of place that makes you want to linger.
You and your person can sip through a flight of reds, whites, or bubbly while looking out over the vineyard. Sometimes there’s live music playing on the patio, and it just adds to the whole slow, romantic vibe. Grab a table, split a charcuterie board, and let the afternoon unfold. No rush, no plans—just good wine and great company.
And if you’re into extra touches, their on-site restaurant is actually pretty amazing. Go ahead and make a reservation—your future date-night self will thank you.
- Pros: Gorgeous setting, solid wine selection, feels like a mini vacation.
- Cons: It’s a drive, so plan a designated driver or consider staying overnight nearby if you want to indulge.
3. Catch a Film at a/perture Cinema
If your idea of the perfect date night in Winston-Salem, NC, involves something low-key, thoughtful, and just a little artsy—this one’s for you. a/perture Cinema is not your average movie theater. It’s tucked right in the heart of downtown Winston-Salem and has this old-school, indie charm that makes it feel a lot more personal than the big chain theaters.
The vibe here is intimate—think cozy seats, locally curated films, and a crowd that genuinely loves cinema. You won’t find the latest Marvel blockbuster, but you will find indie gems, international flicks, and documentaries that spark actual conversations afterward. It’s the kind of place where you and your date might leave the theater and immediately start unpacking the film over late-night coffee or a walk through downtown.
Bonus points: They serve wine and local snacks, so you can sip while you watch. Yes, it’s as good as it sounds.
- Pros: Thoughtful film selection, cozy setting, feels like a “cool couple” kind of night.
- Cons: Limited showtimes, so you’ll want to check the schedule and plan ahead.
4. Explore Trade Street Galleries
Some date nights are all about getting dressed up and doing something big. Others? They’re about slowing down, wandering aimlessly, and letting the city surprise you. That’s exactly the kind of night Trade Street in downtown Winston-Salem is made for.
Start your evening with a casual stroll through the Arts District. Pop into a few local galleries—you don’t have to be an art expert to enjoy it, just curious. Each spot has its own vibe, and honestly, half the fun is seeing what catches your eye (or sparks a laugh). If you’re lucky, you’ll stumble into a new exhibit or a live artist talk.
When you’ve had your fill of inspiration, grab a coffee at one of the nearby cafés—Camino is a local fave—or find an outdoor table to people-watch. It’s the kind of unhurried, no-pressure date that makes room for conversation, creativity, and connection.
- Pros: Free, artsy, and full of spontaneous moments.
- Cons: Galleries may close early—go on a Thursday or Friday evening for the best experience.
5. Try a Pottery Class at Earth Sage Studio
Okay, hear me out—pottery is way more fun (and romantic) than you might think. There’s something about working with your hands, getting a little messy, and creating something together that just brings people closer. Earth Sage Studio offers laid-back, beginner-friendly classes where you and your date can shape, spin, and maybe even laugh through the chaos of trying to make a decent-looking bowl.
It’s not about perfection—it’s about the experience. The instructor keeps the vibe super relaxed, and there’s zero pressure to be “good.” You’ll both walk away with something handmade, even if it’s a slightly lopsided cup that becomes your new favorite inside joke.
Bonus: They’ll glaze and fire your pieces so you can come back and pick them up later. Is this a built-in reason for date #2? I think yes.
- Pros: Creative, interactive, and something you’ll actually remember.
- Cons: Classes can book up quickly—definitely reserve your spot ahead of time.
6. Sunset Hike at Pilot Mountain
There’s just something about watching the sun set over a mountain ridge that hits differently. And Pilot Mountain? It delivers. Just a 30-minute drive from downtown Winston-Salem, this spot is perfect when you’re craving fresh air, epic views, and a little space to just… be.
You don’t have to be a hardcore hiker to enjoy it, either. The trail to the summit is manageable, and there are lookout points close to the parking area if you’re keeping things chill. Once you’re up top, you’ll see why people keep coming back—the views stretch for miles, and when the sky starts to glow pink and orange, it feels like you’re standing in a painting.
Bring a blanket, a couple of snacks, and maybe even a thermos of wine or cider (just be respectful—it’s still a park). It’s peaceful, beautiful, and hands-down one of the best ways to end a summer evening.
7. Picnic at Salem Lake
If you’re after a laid-back kind of date in Winston-Salem, NC—the kind where you can breathe, snack, and just enjoy each other’s company—Salem Lake is such a solid pick. Tucked just a few minutes from downtown, it feels like you’ve escaped into nature without actually having to go very far.
There’s a 7-mile trail that loops around the lake if you’re in the mood for a walk, but honestly? Just pack a picnic, find a spot near the water, and settle in. Bring your favorite sandwiches, a soft blanket, maybe even a little speaker for background music. It’s the kind of spot that invites conversation—and sometimes those simple, quiet moments turn out to be the most meaningful.
Pro tip: swing by a local bakery or coffee shop on your way and make the picnic extra sweet.
- Pros: Peaceful setting, free to visit, great for both early dates or longtime couples.
- Cons: Not much shade in some areas—so bring sunscreen or find a picnic table under the trees.
8. Candle-Making at Wick & Pour
There’s something oddly romantic about crafting something together—especially when it smells this good. At Wick & Pour in Winston-Salem, you and your date can create your very own custom-scented candles from start to finish. It’s hands-on, a little playful, and way more fun than you’d expect.
You’ll start by picking your favorite scents (think: lavender, sandalwood, or something more unexpected like toasted marshmallow), then mix and pour your candle while chatting at one of their cute workstations. And once it’s cooled? You both get to take home your very own reminder of the date. It’s like the modern version of friendship bracelets—but it smells better.
It’s especially great if you’re not into the usual dinner-and-a-movie routine and want to try something fresh. Plus, who doesn’t love a good candle?
- Pros: Unique, interactive, and you get a keepsake.
- Cons: Candles take about an hour to set—so grab a coffee or dessert nearby while you wait.
9. Dessert Crawl Downtown
Look, dinner is great and all—but have you ever skipped straight to dessert? Winston-Salem’s downtown is packed with spots that serve up treats worth building an entire date night around. Think of it as your own little sugar-fueled adventure.
Start at Delicious by Shereen for some of the fluffiest cupcakes you’ll ever bite into. From there, head to Black Mountain Chocolate Bar, where the smell alone is enough to make you fall in love (with the chocolate, or your date—it’s a toss-up). Don’t leave without trying their macarons or sipping their chocolate cocktails. Finally, wrap things up with a scoop (or two) from Cugino Forno. Their gelato? Chef’s kiss.
Take your time between stops, walk the downtown loop, and maybe even rate your favorites as you go. It’s playful, casual, and a guaranteed good time.
- Pros: Delicious, fun, and totally customizable based on your cravings.
- Cons: Sugar crash is real—maybe skip the pre-date espresso unless you’re ready to bounce off the walls.
10. Live Music at The Ramkat
Some date nights in Winston-Salem, NC, call for something loud, fun, and totally energizing—and The Ramkat brings that vibe every time. It’s one of Winston-Salem’s go-to spots for live music, and whether it’s a rising local artist or a bigger name on tour, the energy here is always electric.
The venue itself strikes that perfect balance—it’s big enough to feel like a real concert, but small enough that you’re never too far from the stage. Grab a drink from the bar, stake out a spot near the front, and let the music do the heavy lifting. You can dance, sing along, or just vibe out together—whatever your style is, The Ramkat makes it feel like a shared experience.
Plus, it’s right downtown, so grabbing dinner or drinks before the show is super easy.
- Pros: Great sound, good energy, and perfect for couples who bond over playlists.
- Cons: Standing room only for most shows—wear comfy shoes and maybe skip the heels.
11. Stargazing at Hanging Rock
This one’s for the romantics. If you’ve ever wanted to end a date under a sky full of stars—no city lights, no noise, just quiet and wonder—Hanging Rock State Park delivers. It’s about a 45-minute drive from Winston-Salem, but once you get there, it feels like you’ve left the world behind.
The best time to go is right before sunset. Hike up one of the easier trails (even the walk to the lake is peaceful), find a cozy spot, and just wait. As the sky fades from gold to deep blue, the stars slowly start to show up. Bring a blanket, maybe a thermos of hot cocoa or wine, and you’ve got the makings of a date that feels straight out of a movie.
And no telescope required—you’ll see constellations with the naked eye. But if you do bring one? Even better.
- Pros: Peaceful, private, and incredibly romantic.
- Cons: It’s a bit of a drive, and the trails get dark fast—bring flashlights or headlamps just in case.
12. Paint & Sip Night
You don’t have to be an artist to enjoy a paint & sip night—in fact, the worse your painting turns out, the funnier the date becomes. Spots like Wine & Design in Winston-Salem host these laid-back art nights where you and your date get step-by-step instructions to paint something fun while sipping wine (or whatever your drink of choice is).
The vibe is super relaxed—no pressure, no judgment, just laughter, color, and good conversation. You sit side by side with paintbrushes in hand, wine glasses nearby, and a room full of people doing the exact same thing. It’s part cozy date, part creative experiment, and part bonding session that always ends in at least one accidental masterpiece.
And the best part? You get to take your painting home—instant souvenir from a night that’s anything but ordinary.
- Pros: Fun, casual, and creative. Great for breaking the ice or trying something new together.
- Cons: Can get a little messy—maybe skip your nicest outfit and opt for comfy-cute instead.
13. Jazz or Comedy Night at Gas Hill Drinking Room
If you’re looking for a date night spot in Winston-Salem, NC, that feels effortlessly cool—but without trying too hard—Gas Hill Drinking Room is it. Tucked upstairs at The Ramkat, this moody little venue is perfect for couples who want to sip something strong and vibe out to live jazz, acoustic sets, or even catch a stand-up comedy night that makes you laugh until your cheeks hurt.
The space itself feels intimate in the best way—dim lights, chill crowd, and a bar that knows how to mix a solid cocktail. It’s the kind of place where conversation flows easily between sets, and you can lean in a little closer without shouting over a crowd.
Whether you’re soaking in smooth saxophone solos or cracking up at a local comic, this is one of those dates that feels spontaneous but special.
- Pros: Great atmosphere, strong drinks, and something different than your usual night out.
- Cons: Events vary by night—check the schedule ahead so you don’t show up on a quiet evening.
14. Go Llama Trekking at Divine Llama Vineyards
Yes, this is real. Yes, it involves wine. And yes, it’s every bit as fun and memorable as it sounds.
Just a short drive from Winston-Salem, Divine Llama Vineyards offers a truly one-of-a-kind date experience: llama trekking through the vineyard trails. You and your date each get paired with a fuzzy, funny, and surprisingly chill llama to walk beside while taking in views of the rolling hills and sipping on some seriously good local wine afterward.
It’s part outdoorsy adventure, part animal therapy, and part “OMG are we really doing this right now?” in the best way. You’ll laugh a lot, probably take a million pictures, and walk away with a story you’ll be telling for years. And after your trek, you can relax with a tasting on the patio, surrounded by grapevines and mountain views.
- Pros: Unique, playful, and full of Instagram-worthy moments.
- Cons: Llamas can be, well… llamas. Embrace the unpredictability and go with the flow.
15. Visit Old Salem Museums & Gardens
If you’re the kind of couple who loves meaningful moments and learning something new together, a stroll through Old Salem might just be your perfect slow-paced date. This historic district feels like stepping back a couple hundred years—cobblestone paths, restored buildings, costumed interpreters, and the smell of fresh-baked bread wafting through the air.
Wander hand-in-hand through the gardens, peek into the Moravian shops, and definitely stop for some old-fashioned cookies at Winkler Bakery (the sugar cake is a must). Whether you do a self-guided tour or go full history mode with museum passes, it’s a peaceful, walkable, and surprisingly romantic way to spend an afternoon.
And if you’re both into history or cozy cottage-core vibes? You’ll feel completely in your element.
- Pros: Charming, educational, and totally different from the usual date spots.
- Cons: It’s quieter and more daytime-oriented—so it may not be ideal if you’re looking for nightlife.
16. Arcade Date at Reboot
Sometimes, you just want to let your inner kids out to play—and Reboot Arcade Bar is the ultimate place to do it. Tucked in downtown Winston-Salem, this retro-inspired bar is packed with old-school arcade games, neon lights, and enough nostalgia to keep you smiling all night.
Challenge your date to a round of Pac-Man, get a little competitive over skee-ball, or team up in a vintage shooter game. All while sipping on craft beer or cocktails from the bar. The music’s fun, the vibe is relaxed, and the whole place just invites you to let loose and enjoy being silly together.
It’s low-pressure, high-fun, and perfect for couples who want to do something different than the usual dinner and drinks.
- Pros: Super fun, affordable, and great for conversation and laughs.
- Cons: Can get loud during peak hours—go earlier in the evening if you want more chill vibes.
17. Day Trip to Mount Airy
If you’re in the mood for a slower kind of date—the kind where you stroll, snack, and maybe even feel like you’ve time-traveled a bit—Mount Airy is the move. Just under an hour from Winston-Salem, this charming small town is famously known as the inspiration for Mayberry in The Andy Griffith Show, and it fully leans into those nostalgic, hometown vibes.
You and your date can wander along Main Street, popping into vintage shops, grabbing ice cream from an old-fashioned soda fountain, and maybe even touring the Andy Griffith Museum if you’re feeling curious. There’s also a handful of cozy diners and antique stores that make you want to slow down and linger.
It’s not flashy or packed with activities, but that’s kind of the point. It’s the kind of date where you reconnect—not just with each other, but with the simple things.
- Pros: Easy drive, adorable town, totally different pace.
- Cons: Best as a daytime date—most spots close early, and it’s a pretty quiet scene at night.
Wrapping It Up
Winston-Salem might not always shout its charm from the rooftops—but if you know where to look, it quietly offers some of the most thoughtful, creative, and genuinely fun date spots around. Whether you’re planning a sweet first date, celebrating an anniversary, or just trying to switch things up on a random Wednesday night, this city totally shows up for couples.
You don’t need to spend a ton of money or plan something over the top. Some of the best moments come from walking hand-in-hand through a quiet garden, sharing cupcakes downtown, or laughing over a totally failed pottery creation. And if you’re willing to drive just a little outside the city? Even more magic awaits.
So go ahead—bookmark this list, share it with your person, or surprise them with something they’ve never done before. Love is in the little things… and Winston-Salem is full of them.
💬 Got a favorite spot that didn’t make the list? Drop it in the comments
📌 Don’t forget to bookmark this post for your next romantic escape.
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FAQ’s
Are there any fun indoor date ideas in Winston-Salem?
Yes! You can take a pottery or candle-making class, catch a movie at a/perture cinema, or enjoy live music and cocktails at The Ramkat or Gas Hill Drinking Room.
What are some unique or quirky date ideas in Winston-Salem?
Try llama trekking at Divine Llama Vineyards, attend a themed paint-and-sip night, or play retro games at Reboot Arcade Bar.
What can couples do for free in Winston-Salem?
Take a walk through Old Salem, have a picnic at Salem Lake, explore the downtown art galleries, or attend the monthly Gallery Hop.
What are some good date ideas just outside Winston-Salem?
Hanging Rock State Park is great for hiking and stargazing, while Mount Airy makes a charming day trip filled with small-town nostalgia.
Where can I go for a first date in Winston-Salem?
Downtown Winston-Salem is perfect for a first date — start with coffee or dessert at Camino Bakery, take a walk along Trade Street, and maybe catch a film at a/perture cinema.
