48 HOURS IN WINSTON-SALEM

Kick off summer in style with a month full of fun in Winston-Salem. A mere three-hour drive from Wilmington, Winston-Salem is where history meets haute cuisine — and where summer comes alive with unforgettable energy. This charming North Carolina city, once defined by its tobacco tycoons and industrious past, has reinvented itself into a spirited weekend destination where cobblestone streets, culinary artistry, and Southern hospitality intertwine.

Day One: Arrival and Indulgence

2:00 p.m. – Check into Hotel Indigo Start your weekend in style at Hotel Indigo Winston-Salem, a boutique gem in the restored 1928 Pepper Building downtown. With sleek, art-infused rooms and panoramic city views, it's a stylish launch pad for everything on your itinerary — walkable to galleries, music venues, and the summer buzz of Fourth Street.

4:00 p.m. – Coffee & Culture at Krankies Fuel up at Krankies, a local favorite roasting up small-batch coffee in a converted warehouse that now serves as a hub for artists, creatives, and coffee aficionados. If you're lucky, you might catch a pop-up market or summer patio performance here.

6:00 p.m. – 3rd Street Soundwaves at Kaleideum (June 6 only) If your visit aligns with June 6, don't miss 3rd Street Soundwaves. Dance to live Latin rhythms by West End Mambo and soak in the summer vibe with street food, cold drinks, and interactive museum fun for just $5 admission. It's the kind of high-energy local experience that perfectly kicks off a Winston-Salem weekend.

7:30 p.m. – Dinner at Sir Winston Head back downtown for dinner at Sir Winston, located conveniently inside Hotel Indigo. This elevated Southern bistro serves up locally inspired dishes with modern flair. From bourbon-glazed pork chops to shrimp and Anson Mills grits, every bite is a warm welcome to Winston-Salem's culinary scene.

8:30 p.m. – Nightcap at Fair Witness Fancy Drinks

After dinner, stroll over to Fair Witness for a cocktail (or two). This speakeasy-style bar crafts inventive drinks in an ambience perfect for unwinding or continuing the vibe from the dance floor.

Day Two: Savor, Stroll & Celebrate

9:00 a.m. – Moravian Breakfast at Winkler Bakery

Begin your morning with the time-honored taste of Moravian sugar cake and warm wood-fired bread at Winkler Bakery, where the scent of history still lingers.

11:00 a.m. – Arts District Ramble

Spend the late morning exploring the Trade Street Arts District, brimming with colorful murals, indie galleries like Delurk, and local shops. During summer weekends, you'll often stumble upon street performers or a mini arts festival along the way.

1:00 p.m. – Lunch & Wine Tasting at JOLO Winery and EndPosts

Spend a sun-soaked summer afternoon at JOLO Winery & Vineyards, just a short drive from Winston-Salem. Enjoy a relaxed wine tasting paired with a seasonal lunch at End Posts, the winery’s elegant on-site restaurant. Dine al fresco with panoramic views of Pilot Mountain, savoring fresh summer flavors and award-winning wines in a picturesque setting made for lingering.

5:30 p.m. – Sip & Savor at Incendiary Brewing

Set in the revitalized Bailey Power Plant, Incendiary Brewing is the ultimate summer hangout. With open-air seating, local food trucks, and live music on weekends, it's the kind of place where you'll linger longer than planned.

7:30 p.m. – Dinner at Six Hundred°

Close out your Saturday with fire-grilled perfection at Six Hundred°. Known for its wood-fired cooking and farm-to-flame menu, this hot spot blends fine dining with bold, smoky flavors. Don't skip the ember-roasted vegetables or their signature steak.

Day Three: Sweet Send-Off

9:00 a.m. – Krispy Kreme Pilgrimage

Make one final (and necessary) stop at the original Krispy Kreme location on South Main Street. There's something deeply satisfying about watching the conveyor belt roll out hot-glazed originals while locals and tourists gather like bees to sugar.

10:00 a.m. – Reynolda House Museum of American Art

Dive into American art history at Reynolda House, the former Reynolds estate turned museum. The stunning gardens are in full bloom during the summer, perfect for a stroll after viewing works by O'Keeffe, Stuart, and Hopper.

12:00 p.m. – Farewell Lunch at Theodore's Bar & Market

Before you hit the road, treat yourself to one last meal at Theodore's, where seasonally inspired, elevated Southern cuisine meets warm, elegant ambience. The crispy chicken sandwich, artisan salads, and signature cocktails make for a perfect finale to your Winston-Salem weekend — one last delicious memory before the drive home.

If your dates align, don’t miss these standout summer events.

Some are tied to specific weekends, but Winston-Salem is alive with music, markets, festivals, and local flair all season long. There’s always something happening — and you can explore the full lineup of summer fun HERE.

June 6 – 3rd Street Soundwaves at Kaleideum

Dance in the streets at this free outdoor concert series in front of Kaleideum. West End Mambo, Winston-Salem's legendary Latin/Salsa band, will bring the rhythm. Enjoy food, beer, and wine on-site, plus $5 museum admission for those who want to explore inside.

Time: 6–9 p.m. | Cost: Free

June 11 – Reynolda Drinks @ Dusk (21+)

Spend a summer evening at Reynolda House Museum of American Art, enjoying cocktails, music, and twilight views of the historic estate. Participate in a scavenger hunt and relax in the Babcock Wing with food trucks and curated drinks.

Time: 6–8 p.m. | Cost: $25 (includes two drink tickets)

June 14 – Winston-Salem Pride Festival & Parade

Celebrate love, equality, and community during this vibrant city-wide Pride event. The parade brings color and joy through the downtown streets, followed by a day filled with live entertainment, vendors, food, and family-friendly fun.

Time: All Day | Cost: Free

June 21 – Juneteenth Festival

Honor Black history and culture at Winston-Salem's annual Juneteenth Festival. Enjoy live music, spoken word, artisan vendors, historical exhibits, food trucks, and more in this joyful celebration of freedom and heritage.

Time: All Day | Cost: Free