Every evening around 8 p.m., guests gather in the parlor of Winston-Salem’s historic Brookstown Inn, where a wood-burning fire, dark mahogany furnishings and walls, comfy leather couches, and colorful paintings by local artists set the stage for a nostalgic end to the day: milk and cookies.
“It’s a nice space to sit and gather your thoughts,” Allison Watts says, the inn’s director of sales. “It feels like home.” The 1837 hotel was originally constructed as the hydroelectric Arista Mill, and today the rooms embrace those architectural features. All exude warmth: floor-to-ceiling windows flooded with sunshine, hand-laid bricks, wooden pine beams.
Across Winston-Salem, shorter days transition into long evenings that are especially cozy, thanks to attractions that feed our soul and nourish our spirit. When you plan a cool-weather visit to the city of arts and innovation, make yourself at home with these seasonal favorites.
Discover authentic, legacy-driven experiences in Winston-Salem. Stroll centuries-old sidewalks that share stories of the past while leading you into a world of modern art, flavor, and innovation. It’s history and modern charm, perfectly paired — because here, it’s Twice as nice.
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Dressed in period clothing, the interpreters at Old Salem show visitors how the Moravians lived in the 18th century. Photography courtesy of Visit Winston-Salem
For Watts, nothing epitomizes the aroma of winter in Winston-Salem like Old Salem, a historic district filled with museums, gardens, living history, and live demonstrations. “It’s hard to describe it, but you pick up hints of Moravian sugar cake, beeswax candles, and woodburning fireplaces,” she says. “That smell is why I like to visit around the winter season.”
As you walk into Winkler Bakery, founded in 1807, you’ll get the true Moravian cookie-making experience. Bakers wear traditional period clothing as they showcase time-honored cooking methods. Pick up a Moravian sugar cake to go; they freeze well, so you can warm it up — and make your house smell like a bakery — year-round. “I love it for breakfast on Christmas morning,” Watts says.
Be sure to pop into the Single Brothers’ House on Main Street, the largest half-timber building in North Carolina built as a residence for unmarried Moravian men living in Salem in the 18th century. Here, costumed interpreters demonstrate many of the trades that were commonplace at the time, like pottery, shoemaking, and weaving.
Have lunch at Old Salem’s Muddy Creek Café & Listening Room, where you can get a slice of traditional Moravian chicken pie or a bowl of soup and hot panini. Check their events calendar for live music on the horizon.
Beat the cold and cozy up with a showing at a/perture cinema. Choose from a selection of indie films or documentaries. photograph by Kristen Bryant
Slip away into the alternate universes depicted in new and classic films inside a small, art-house environment at a/perture cinema on 4th Street. With a lineup of independent films and documentaries you won’t find anywhere else, the nonprofit theater lives up to its mission to engage and entertain the community with thought-provoking and inspiring films.
With four cinemas for showings, it’s warm and cozy in the comfortable, intimate studios, but what’s truly heart-warming here is the community of theater buffs who set the world aside for a few hours to get lost in a good story with a bag of popcorn.
Indulge your sweet tooth with a made-to-order cake doughnut from Dough-Joe’s. Try a hot classic glazed or their seasonal specials. Photography courtesy of Visit Winston-Salem
The “Hot Doughnuts Now” sign has long been a Winston-Salem icon since Krispy Kreme opened in 1937. Today, the now-international chain is joined by lots of sweet company to keep visitors sugared up.
On a Saturday or Sunday morning when she has time to get a cup of coffee and stroll around, Watts heads to Dough-Joe’s in Reynolda Village. Known for their made-to-order, cake-like doughnuts and café that feels straight out of an artistic farmhouse, the coffeehouse invites you to sit and stay for a while or take your treats to go.
“Even in the winter, it’s calming to walk the grounds around Reynolda House,” she says. “It’s serene and refreshing, but also historic, which has a warm feeling for me.”
Just down Reynolda Road in the West End district, a mother-daughter duo mastermind the treats at Louie & Honey’s Kitchen. Try the Amish cinnamon rolls, inspired by a family recipe and European baking techniques.
For a display of treats both mouthwatering and beautiful — twice-baked almond croissants with chocolate, pull aparts with sliced almonds and plump raisins; orange-cream éclairs — stop by Bobby Boy Bakeshop, also on Reynolda Road in the Buena Vista neighborhood.
Built up around the 1890s, Winston-Salem’s oldest West End neighborhood holds its fair share of secrets. Make time to hear about them on one of Carolina History & Haunts’ West Endings ghost tours. About 90-minutes long, the candlelight tour strolls West End’s Victorian homes and takes participants on a time-traveling adventure all the way back to the Revolutionary War.
When the tour’s complete, settle in with a glass of wine and dessert at Manolo’s Boutique Wines & Bistro, inside a historic West End house. We recommend the tiramisu or chocolate mousse.
The nationally renowned Mission Pizza is a must-visit spot for wood-fired pizza. Photography courtesy of Visit Winston-Salem
There’s something extra decadent about a wood-fired pizza, especially when it’s fresh out of the oven at Mission Pizza Napoletano. At the helm of this small osteria is Chef Peyton Smith, who boasts a dizzying list of accolades.
Smith’s pizza-making journey began with a wood-fired oven in a trailer back in 2010. Four years later, he officially opened Mission Pizza in an Arts District building on Trade Street. He was a semifinalist for the James Beard Award for Best Chef Southeast for his Neapolitan-style pies in 2022. And this year, the annual Top 50 Pizza USA guide — a Michelin-style ranking organization — rated Mission Pizza 19th best in the country.
Word about Mission Pizza has spread; you’ll want to make a reservation to savor one of Smith’s Italian-inspired masterpieces, recognizable by their slightly charred, puffy, and perfectly chewy crusts. Like Smith and his pizza, the dimly lit restaurant’s decor is non-fussy and authentic, the ideal destination to warm up and fill up.
Let the afternoon fade into the evening as you enjoy a wine tasting then dinner at JOLO Winery & Vineyards. Photography courtesy of Visit Winston-Salem
Relax by the fire in Childress Vineyards’ tasting room with a glass of award-winning wine.
Outside of Winston-Salem, more than 40 wineries in the Yadkin Valley AVA await exploration. If you want to curl up in an atmosphere reminiscent of an Italian manor, enter through the grand, curved doorway at Childress Vineyards in Lexington, a short 30-minute drive from downtown. Make yourself comfortable in the tasting room. Sip a flight of wines ranging from reds and whites to even mimosa flights. In nearby Pilot Mountain, JOLO Winery & Vineyards offers tastings of their award-winning wines. Book a dinner reservation for afterwards at their on-site EndsPost Restaurant.
Where will you begin? Whether you wake up with a still-warm treat or save your cookies for an evening by the fireside, a weekend in Winston-Salem is the perfect tonic to the winter’s chill. Click here to start planning your visit.
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