Head north to JOLO Winery & Vineyards for their Cuvee Tasting Experience, which includes a flight of five wines paired with four different food items. This experience will be offered Feb. 15-16, and you’ll need reservations. Shelton Vineyards will also be having Valentine’s Weekend specials like exclusive wine tastings, romantic vineyard tours, and a special Valentine’s menu at the Harvest Grill, Feb. 14-15. Saturday, Feb. 15, is also when Raffaldini Vineyards is hosting their Four Seasons Winter Wine Dinner. With over 40 wineries in the Yadkin Valley, you can also book a tour to visit other local wineries for tastings.

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 expert suggestions, here are a dozen local favorites hand-picked by Visit Winston-Salem staffers.

Spring House Restaurant, Kitchen & Bar 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. For first dates, 6th and Vine in the Downtown Arts District is an ideal choice thanks to its cozy, inviting atmosphere and ever-evolving wine list. While the menu is somewhat modest, the salads and small-plate options here are top-notch. If a memorable meal is what you're after, Bernardin's Restaurant at the historic Zevely House 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:

• Founders Restaurant located inside the Shaffner Inn
• Mozelle's Fresh Southern Bistro
• Sushi Rose
• Cibo Trattoria
• The Downtown Grille
• Fratellis Italian Steakhouse

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

At the heart of Winston-Salem's creative soul is Sawtooth School for Visual Art, a downtown institution offering hundreds of classes annually in 11 different mediums. Couples can check out their one-night Taste of Art workshops, where you'll spend a few hours creating a work of art to take home. 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. 

Elsewhere downtown, Mixxer Makerspace hosts classes on Saturdays and a few throughout the week. A few examples of current offerings are making a copper wind chime or a unique ceramic tile. As a bonus, it's conveniently situated near popular local breweries and entertainment venues.

Looking for a little playful experimentation? Check out Dabble Art Bar in the West End Mill Works Complex. Couples can choose from various self-led art activities, such as collaging, watercolor painting, stamp making, air-dry clay sculpting, drawing, and coloring, all designed for beginners. The casual, coffeehouse-like atmosphere makes it easy to connect and create together.

Bring your own wine and enjoy an evening of guided fun at Wine & Design. The downtown studio offers several couples-themed events in February where partners collaborate on a two-canvas painting. Additionally, there's a special Galentine's Party on Thursday, February 13, perfect for celebrating with friends. 

Live music fans will find plenty to love in Winston-Salem. Throughout the month (and nearly every night of the week), local talent shines brightly at dozens of local bars, clubs, and other venues in town. Whatever style you prefer, from blues and jazz to indie rock and country, you're sure to find it here. You can find details on upcoming live-music events on our Events Calendar, but here are a few concerts happening around Valentine's Day weekend:

• Local favorite Jeffery Dean Foster & The Arrows will be playing at The Ramkat on Saturday, Feb. 15.
• On Sunday, Feb. 16, you can attend the Camel City Jazz Orchestra  Presents Big Band Brunch, which includes a jazz performance and brunch buffet.
• If you want something a little more laid back, you can catch live music all weekend at the Foothills Brewing Tasting Room where they serve wine, cocktails, and other drinks in addition to their brews.
• UNCSA has a couple of different performances over the weekend from a brass quintet to a clarinet and piano recital focused on women composer.

The Reynolda House is known for its rich history, but it also serves as one of the city’s best collection of American art. The new Andrew Wyeth Exhibit will open on February 15 and run through the end of May. The North Carolina Museum of Art Winston-Salem (formerly SECCA) serves to connect southeastern contemporary art to the art world at large and is one of the perfect Winston-Salem date ideas for art lovers. You can also take a stroll through the Downtown Arts District to check out a few local art galleries and public art, including Visual Index and the Piedmont Craftsmen Gallery to name a few.

The Lam Museum of Anthropology houses many archaeological artifacts and is North Carolina’s only museum dedicated to the study of global cultures. One of their current exhibits is Poems Made to Wear: Traditional Colors in East Asia, which features clothing from China and Japan and the connection of color, nature, and fashion.

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! 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.

ROAR brings the excitement all day in Winston-Salem, making it a perfect spot to add to your romantic getaway list! Play arcade games, go bowling, try a new spin on putt-putt, or test out a sports simulator all in one place. They even have bars, a beer wall, and multiple restaurants, so you don’t have to leave to find dinner. Perfect for when the weather is chilly! They’re also hosting a Valentine’s Day event on February 13 where their Trivia Night will be Valentine’s themed.

The Graylyn 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, you can book their Celebrate Good Times 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 has a Luxury Getaway package. 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.

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