With more than 40 wineries in the Yadkin Valley, most within a 30-minute drive of Winston-Salem, there’s no shortage of wine-focused date ideas. While guided tours are always an option, many wineries also host intimate tastings and seasonal experiences that feel especially well suited for a romantic outing.

JOLO Vineyards, 30 minutes north of downtown, is known for its special events and elevated tasting experiences. Its popular Cuvee Tasting Experience features a flight of five wines paired with four food items and is offered monthly by reservation. For Valentine’s season in 2026, JOLO also hosts a Galentine’s Day celebration on Feb. 13, complete with a four-course meal, paired wines, and a lively atmosphere, along with a Valentine’s Day dining experience at its award-winning restaurant, End Posts. Reservations are required.. (See more details on upcoming events here.)

Elsewhere in the Yadkin Valley, Shelton Vineyards offers Valentine’s Weekend specials from Feb. 13–15, including exclusive tastings, romantic vineyard tours, and a special menu at the Harvest Grill. And at Raffaldini Vineyards, often considered the region’s most picturesque winery, February brings events like a Valentines Amore Brunch on February 15 and the Four Seasons Wine Dinner on Feb. 28.  

Learn more about Yadkin Valley Wine Country, including standout vineyards, tour options, and more, by visiting our Wineries & Vineyards page.

Whatever food or vibe you're looking for this Valentine's Day, you'll find something perfectly suited to your taste. There are countless places for to eat, drink, and love in Winston-Salem, each with their own unique charms. If you're looking for tips, here are a dozen local favorites hand-picked by our staff.

The Spring House is a great choice between their fun cocktail menu and the ambiance of dining in a historic home. The setting is a sight to behold (there's really nothing else like it in town), and the onsite Library Bar is a perfect place to grab a drink before or after your meal. 

The Katharine Brasserie & Bar is another popular date spot, with its art-deco decor and Parisian brasserie-inspired menu. Located on the ground-floor of the Kimpton Cardinal Hotel, the chic eatery is equal parts fun and finesses.

Looking to make a good impression? Meridian Restaurant is a date-night staple downtown, hallmarked by a casual-elegant ambiance, open kitchen layout, and innovative tapas menu--perfect for sharing. If a memorable meal is what you're after, Bernardin's Restaurant at the historic Zevely House (pictured) is one-of-a-kind. Set in a century-old brick home, the eatery offers a perfect balance of history, charm, and deliciousness (not to mention one of the best year-round patios in town).

Some more favorite spots for a memorable Valentine's dinner include:

• Mozelle's Fresh Southern Bistro
• Ryan's Restaurant
• Rooster's: A Noble Grille
• Sushi Rose
• Cibo Trattoria
• The Downtown Grille
• Fratellis Italian Steakhouse

For a complete list of restaurants in Winston-Salem, click here.

Few dates are more memorable than making something side by side. At Sawtooth School for Visual Art, couples can sign up for one-night Taste of Art workshops, creating everything from ceramics and jewelry to glass and printmaking in a relaxed, beginner-friendly setting.  Multiple classes are held each Friday and several Saturdays in February, including a few uniquely themed for Valentine's. See the full Taste of Art schedule here.  

Also downtown, Mixxer Makerspace offers short classes in hands-on projects like metalwork or ceramics—perfect for couples who like to experiment, with breweries and nightlife close by. And in nearby West End,  Dabble Art Bar  at West End Mill Works lets you drop in for self-guided activities like watercolor, collage, or clay sculpting in a cozy café atmosphere. You can also sip and paint together at Wine & Design in downtown or Uncorked Masterpieces in Reynolda Village, but of which offer couples-themed experiences throughout the year, including Valentine classes.

Not all creative dates involve an easel. Some start in the kitchen. Decorating cakes together is equal parts playful and rewarding at the Canvas Cake Studio on Jonestown Road, where hands-on classes guide couples through buttercream techniques, fondant details, and colorful designs. No baking experience is required, just a willingness to get creative and a little messy. The studio regularly offers couples-themed classes, especially around February. Check their website for upcoming themes.

For a more savory spin on creative time together, Southern Home & Kitchen at Thruway Center offers cooking classes that feel both social and inspiring. This specialty kitchen shop and cooking studio hosts popular demonstration-style classes, with occasional hands-on options. Classes often sell out, so it’s worth checking their event calendar early when planning your date.

Live music fans will find plenty to love in Winston-Salem, where shows happen nearly every night of the week. Local and touring talent take the stage at bars, clubs, and concert halls across the city, spanning genres from blues and jazz to indie rock, punk, and country. February’s lineup includes fan-favorite rocker Corey Smith, Fleetwood Mac tribute band Tell Me Lies, and legendary punk group Dead Boys. For a snapshot of what’s coming up, browse our our Live at the Ramkat blog for featured shows and artist highlights.

While Ramkat anchors the city’s mid-sized concert scene, it’s far from the only place to catch a great show. The Joel Coliseum regularly brings major touring acts to Winston-Salem. This month, rising country stars Parker McCollum (Feb. 12) and Cody Johnson (Feb. 27) headline the venue. Check the coliseum’s event calendar for upcoming performances.

Smaller venues add to the city’s musical personality. Monstercade leans toward indie, punk, and grunge, while Earl’s Whiskey Bar features country and rock. Muddy Creek Cafe is known for Americana, roots, and singer-songwriter sets, and several local breweries, including Wise Man, Joymongers, Fiddlin’ Fish, and Foothills, host regular live music. In warmer months, free outdoor series take center stage, from Friday’s Downtown Jazz to Saturday’s Summer on Fourth and the growing CoalPit Live series. For a full rundown of venues and recurring concerts, explore our Live Music Guide. 

Exploring Winston-Salem’s arts scene is an experience in itself, anchored by the Downtown Arts District, the heart of the city’s nationally recognized creative community. A stroll through the district reveals a mix of galleries, public art, and working studios, including stops like Visual Index and Piedmont Craftsmen Gallery, where local and regional artists take center stage.

The city’s major art institutions are also in a season of transformation, with compelling options still available to visitors. Reynolda is known for its historic setting, strong American art collection, surrounding gardens, and its boutique retail district (Reynolda Village). While the historic house museum is closed for renovation through the first half of 2026, Reynolda’s Babcock Wing reopens this spring with Layered Looking (March 10–July 19), an immersive exhibition inviting visitors to engage with art through touch, sound, and movement. 

For art lovers drawn to immersive experiences, the Van Gogh Experience offers a different way to connect. This ongoing exhibition surrounds visitors with floor-to-ceiling projections, light, and sound across 20,000 square feet, creating a 60–90 minute journey through the artist’s most iconic works. Dates, times, and ticket availability vary, so visitors should check the official website for current details.

To extend the experience beyond gallery walls, consider staying somewhere that feels like art itself. The West Salem Art Hotel is one of the city's most creative lodging options, housed in a former 1930s grocery store and reimagined as a six-room short-term rental. Each themed space is paired with gallery-style common areas showcasing local art for sale, and its under a mile from downtown.

There’s just something about a coffee date that’s a little extra romantic. Whether it’s the cozy atmosphere or the chance to linger over your favorite brew and have a conversation, there are plenty of cozy coffee shops in Winston-Salem.

Louie & Honey’s Kitchen is known for their cinnamon rolls, but be sure to get there early because they do sell out! And take it from us; the coffee here is among the best in town; possibly some of the best in the universe.

Bobby Boy Bakeshop was a James-Beard nominee for Most Outstanding Bakery in 2024, so you can’t go wrong here. Anchor Coffee is another great choice located in the historic Bailey Power Plant. 

If you love books, head to Footnote Coffee & Cocktails where you can sip on your drink and browse through the bookstore next door, Bookmarks.

Check out our Coffee Lover’s Guide for more café date ideas.

Put on your dancing shoes and learn (or refresh) moves together! Best of Ballroom dance studio and Real World Ballroom both offer ballroom, Latin, swing, and other partner-friendly lessons that are perfect for couples or beginners, with group and private options to suit your pace. Local favorite SonCaribe Latin Dance hosts salsa, bachata, and merengue classes and socials — including monthly drop-in lessons followed by dancing at Art For Art’s Sake. 

For a more casual or creative setting, community studios like Juxtaposition Studios sometimes offer adult movement classes, and The Academy of Dance Arts provide structured adult lessons that can be booked as series or individual sessions. Check schedules and preregistration requirements — many welcome drop-ins or short-term sign-ups for a fun date night with rhythm and connection.

Add a little friendly competition to date night at Winston-Salem’s arcade bars, where nostalgia, neon lights, and cocktails set the mood. Start downtown at Reboot Arcade on Liberty Street, pairing vintage games and pinball with craft drinks that make it easy to linger between rounds. Nearby, Camel City BBQ Factory ups the fun with skee-ball and billiards alongside its comfort-food menu, while Dive Bar on Burke Street keeps things lively with Jet-Pong, Guitar Hero, music bingo, and DJ nights.

For a bigger, all-in-one experience, head to ROAR, the multi-level entertainment hub downtown. Following a recent reconfiguration, ROAR’s 50-game arcade now shares the second floor with duckpin bowling lanes, creating a natural hangout for playful competition. The basement level is also home to high-tech mini golf, the Twisted Putter, for this looking for a differnt kind of challenge. Lastly, Roar's 75+ tap, self-serve beer wall and casual bites make it easy to turn a few games into a full evening out. 

Turn a date into a shared adventure with guided tours that mix history, storytelling, and great food. Carolina History & Haunts offers evening ghost walks through Winston-Salem’s West End, where candlelit streets and local legends make for an atmospheric night out. 

For daytime exploring, Triangle Walking Tours dives into downtown’s architecture with its Industrial History tour, inspiring moments with its Black History tour, and explores the city's sinister side in its ultra-fascinating True Crime tours. Triangle has regularly scheduled walking tours on Saturday afternoon and always does custom tours by appointment daily.

If food is your love language, Taste Carolina Food Tours pairs chef-driven bites with local history on Saturday brunch tours or custom private experiences. Rated the top travel experience in the area by AAA, Taste Carolina tours are an easy way to spark conversation while discovering a different side of the city together. In addition to the Saturday brunch tours, custom tours are also available to fit your schedule.

Couples looking to turn a great date into a full getaway have several romantic hotel options across Winston-Salem. 

The Graylyn Estate (pictured) leans fully into romance with packages that may include champagne, chocolate-covered strawberries, fresh roses, and late check out.  The estate has a Valentine’s Weekend package that includes dinner and breakfast for two, late checkout, plus champagne & strawberries in the room. If you're looking for a little pampering, check out their European Touch Spa package, which includes a spa gift certificate, dining credit, and a romantic welcome gift.

At the Kimpton Cardinal Hotel, you can book several love-themed packages, most of which can be customized to your choosing. A popular option includes the Winston-Salem Staycation package, which includes nightly champagne, or upgrade to the Bath & Bubbles Package where you can enjoy that champagne in a large spa-soaking tub. 

If you want to add some history to your stay,  The Historic Brookstown Inn offers popular date-night and luxury getaway packages, Looking to stay closer to the west Winston-Salem / Clemmons area? The Village Inn offers a Romantic Getaway package for their guests. Finally, if you want to stay at a romantic bed & breakfast in the heart of downtown, book a room at The Shaffner Inn or Summit Street Inns. The sister properties don’t always advertise formal romance packages, but their intimate rooms, historic charm, and quiet atmosphere make them natural favorites for couples. 

For a full list of lodging and accommodations in Winston-Salem, click here.