Unforgettable Food & Drink Experiences in Winston-Salem

Planning a visit to Winston-Salem? Come hungry. From chef-led tasting menus and wine pairings to hands-on cocktail classes and cookie factory tours, this city offers far more than just great restaurants—it delivers unforgettable foodie experiences.

Chef Experiences, Pop-Ups & More

Robert Hall Secret Supper Society
Inspired by vintage supper clubs of the 1930s and ’40s, this members-only series pairs themed dinners with inventive cuisine, live performances, and a curated, glamorous atmosphere. Events are held every few months and feature local chefs and rotating themes. Tickets range from $65–$150; memberships are optional. Get more details on the Supper Club by visiting Robert Hall's website.

Pizzakase at Mission Pizza
Chef Peyton Smith, a 2022 James Beard semifinalist, hosts Pizzakase, an omakase-style tasting featuring six to eight surprise mini pizzas, each crafted live at the counter with bold, seasonal ingredients. For a more structured experience, opt for the four-course Prix Fixe menu, served family-style and full of specialty dishes. Learn more at Mission Pizza's website. 

Chef's Tasting Menu at Spring House
Nightly, award-winning Chef Timothy Grandinetti and his team serve a three-course tasting menu highlighting sustainably sourced meats, seafood, and produce. The offerings change daily, so guests are encouraged to call ahead and simply ask, “What’s on tonight’s Tasting Menu?” See more on Spring House's menu offerings here.

Pop-Ups & Fireweed Dinners with Native Root
Chef Jordan Rainbolt weaves her Cherokee and Choctaw heritage into globally inspired dishes like duck-fat cannoli and sweet tea tonkotsu. Her Native Root pop-ups—often hosted at West Salem Public House—celebrate seasonal creativity, while her seasonal Fireweed Dinners offer open-fire cooking, storytelling, and community connection. Follow @native.root on Instagram for event updates.

Supper Series at The Katharine
This ongoing dinner series invites guest chefs to The Katharine’s terrace for seasonal, four-course menus paired with Broad Branch cocktails. Dishes are fun, handheld, and flavor-forward. Supper dates vary, so follow along on Instagram to stay in the loop.

Wine, Beer & Cocktail Experiences

Flights & Bites at Rayson Vineyards
Every Wednesday from 5:30–7 p.m., enjoy a relaxed tasting at Rayson Vineyards in nearby Mocksville (pictured above). Choose from two menus, each featuring three tapas-style dishes paired with three wines, all for just $49. Get more details on Flights & Bites and other menu offerings here.

Pour Tour du Jour at Graylyn
Tour the historic Graylyn Manor House, then unwind with wine and appetizers in the library during this elegant Sunday event (held once or twice a month). Tickets are typically around $60/person. Details and upcoming dates are available here on our website.

Sunday School at EasyTalk
Join a Sunday cocktail workshop at EasyTalk for a hands-on class filled with drinks, games, and expert-led mixology tips. The 90-minute Sunday School classes are offered year-round and include a reserved seat in class, two full-sized cocktails, a cocktail guide, and light bar snacks. Not visiting on a Sunday? You can still enjoy a variety of memorable, cocktail-inspired games, including “Roll the Dice,” where three dice determine your custom cocktail. 

Gourmet Grazing + Pairings at Childress Vineyards
In nearby Lexington, Childress Vineyards offers weekend Gourmet Grazing boards—your choice of cheese or charcuterie—served with wine on the scenic terrace, ideal for 2–4 guests. At the onsite restaurant, The Bistro, enjoy Sundays in the South, a weekly menu featuring Southern comfort classics paired with signature wines. Guided tours and tastings are also available: $15 on weekdays and $25 on weekends.

Brewery Experiences

Gourmet Shakes at Small Batch. Can a milkshake count as a full-on food experience? At Small Batch, the answer is yes. These over-the-top shakes made a name on social media—and now they’re back. Choose from classics like the Black & White (Oreos + chocolate chip cookies) or rotating flavors like Dubai Chocolate. Boozy or not, they’re a treat. See them for yourself here.

Tank Pours at Lesser-Known. Sip straight from the source with “tank pours”—beer served directly from lagering tanks, bypassing the keg. It's one of the unique offerings at Lesser-Known, a microbrewery that focuses on German and Czech styles. See what brews are available via tank pours here.

Beer School at Foothills Brewing. Get a crash course in craft beer during this two-hour session featuring a brewery tour, brewing lesson, and generous sampling at Winston-Salem's legendary Foothills. While public Beer Schools are offered periodically, private or group bookings are typically available year-round. Find more details here.

Local Food & Drink Tours

Taste Carolina Gourmet Food Tours
Walking tours with Taste Carolina offer a delicious downtown experience, often with a brunch theme. You’ll enjoy bites from local staples and hidden gems, plus stories from the city’s culinary scene. Tours are regularly held on Saturdays at 10:45 a.m. and last approximately 3 hours. Private and custom tours can be arranged any day or night for groups.

Triad Trolley Food Tours
Triad Trolleys offers seasonal and private tours take guests to Winston-Salem’s food landmarks—like a Hot Dog Tour that hits the town’s legendary stands (Pulliam’s, Kermit’s, etc), a Farmer’s Market tour celebrating local growers and makers, and a Moravian Cookie Trail that visits beloved bakeries such as Mrs. Hanes, Winkler, and Dewey’s. See all tour options here.

Yadkin Valley Wine Tours
North Carolina’s largest wine tour company, Yadkin Valley Wine Tours offers private excursions from Winston-Salem for groups of 2 to 30. Transportation options vary by group size—from luxury cars to full-size shuttles. Tours last about seven hours and include visits to multiple area wineries. You can customize your itinerary or let the team handle all the planning. See more Yadkin Valley tour options in our Wine & Ride article.

Mrs. Hanes’ Moravian Cookie Tour
Get a behind-the-scenes look at how beloved Moravian cookies are made during this 90-minute tour of Mrs. Hanes’ factory in nearby Clemmons. You’ll visit “Grandma’s Kitchen,” see dough mixed from scratch, and watch the “Artists in Aprons” hand-roll and hand-cut each cookie. Best of all? You’ll sample all six signature flavors along the way. options here.

Broad Branch Distillery Tours
Named North Carolina’s “Distillery of the Year” by the NCRLA, Broad Branch offers monthly tours of its downtown distillery, spotlighting Appalachian traditions and bold, small-batch spirits. Learn how their moonshine-based spirits are made, then enjoy a guided tasting. Public tours ($15) take place at 2 p.m. on the first Saturday of each month; private tours are available year-round. To book, fill out a short request form on the Broad Branch website. 

Party-on-Wheels

• Hook & Ladder Party Pumper. A BYOB bar crawl led by retired firefighters aboard a tricked-out firetruck—complete with music, lights, and fun stops around downtown.
   
• Winston-Salem Trolley Pub. Pedal-powered and perfect for groups, this mobile bar seats up to 14 guests and makes multiple stops downtown. Tours are available nightly; minimum six passengers.

Cooking Classes & Culinary Demos

Old Salem Hearth Cooking
Step into the past with seasonal cooking demos and hands-on classes at Old Salem’s historic sites. Watch 18th-century Moravian meals prepared over open hearths and enjoy tastings with a side of history. Hearth cooking is held at various times year-round; check Old Salem's calendar for upcoming classes.

Southern Home & Kitchen (SoHo)
Located in Thruway Shopping Center, Southern Home & Kitchen offers hands-on weekly classes led by chefs and food writers. Learn techniques and recipes while cooking global dishes—and enjoy the full meal. Private group sessions available. See all upcoming classes.

The Stocked Pot Cooking Studio
This family-run cooking studio on Jonestown Road offers a wide range of classes—from sushi rolling and comfort food to knife skills and liquid nitrogen ice cream. A hit for team-building and special occasions. Get more details on team-building classes by visiting the Stocked Pot website.

Food-Focused Events

While most Winston-Salem events serve up something tasty, these annual favorites put food and drink front and center—making them must-visits for every foodie.

WS Food Truck Festival – various dates
Held two to three times annually in downtown, this lively festival brings together dozens of local food trucks, live music, and unbeatable street eats. The festivals are typically held in May and September in downtown's Industry Hill area, adjacent to Wise Man Brewing.

Greek Festival – May
Hosted by the Annunciation Greek Orthodox Church each May, this beloved event features authentic Greek food, pastries, and dancing.

Rayson Around the World – July
This global food and wine celebration at Rayson Vineyards features curated pairings, artisan vendors, and live music. Following a successful debut in 2025, the event is expected to return even bigger and better next year.

Hispanic League FIESTA – September
This vibrant downtown street festival features international food vendors, cultural displays, and festive Latin flair. Expect bold flavors and big energy. 

Carolina Classic Fair – October
North Carolina’s second-largest fair draws nearly 300,000 visitors. Food is the star—from turkey legs and funnel cakes to only-at-the-fair creations such as Krispy Kreme burgers, deep-fried butter, and “Dilly Dogs” (a hot dog inside a dill pickle). 

Kernersville Oktoberfest – October
Celebrate fall at Körner’s Folly in nearby Kernersville with music, seasonal brews, and bites from local vendors at this German-inspired fest. 

Yadkin Valley Grape Festival – October
Just 25 minutes west of Winston-Salem, this fall festival features wine tastings, food trucks, craft vendors, and live entertainment in charming downtown Yadkinville. 

Triad Restaurant Week – October
Organized by Eat.Drink.Triad, this week-long celebration includes prix-fixe menus at 50+ local restaurants, plus deals for VIP passholders. Stay tuned for the 2025 dates.

Hungry for More?

This list is just the beginning. Head over to the Food & Drink section of our website for even more ways to savor Winston-Salem. Discover chef spotlights, seasonal stories, and one-of-a-kind culinary events. You’ll also find a full directory of local restaurants, bakeries, breweries, coffee shops, vineyards, and more