Our tour guide: Barbara Gallimore. photograph by Stacey Van Berkel

Editor’s Note: This story was published in 2022 and updated in 2023.

Evergreen wreaths wrapped in lights and adorned with dark red bows stretch across Sunset Avenue, creating a sort of cheery tunnel through downtown Asheboro. Streetlamps are decorated with snowflakes and tinsel trees. In Bicentennial Park, schoolchildren hang ornaments on their class Christmas tree in preparation for the parade. At The Flying Pig Food & Spirits, Asheboro native Barbara Gallimore is trying to keep up with the demand for her seasonal red velvet cheesecakes. She loves this time of year: “The city does a great job decorating the park, and there is a huge Christmas tree right outside The Flying Pig. Tons of people come to get their picture made by that tree.”

For Gallimore, the warm holiday feeling reminds her of her childhood. She grew up with “15 mothers,” she says, “because everybody looked after everyone else’s kids.” While Asheboro has grown, scratch-made birthday cakes from Central Bakery and hot dogs from Hop’s Bar-B-Q are still downtown staples. “There is a huge sense of community here,” Gallimore says. Around dinnertime during the parade, people find a spot on the sidewalk outside The Flying Pig to watch the floats pass by. “When people come in,” Gallimore says, “they’re in a good mood, and everyone is festive.”

Eat

The Flying Pig Food & Spirits. Gallimore opened The Flying Pig with her husband, Dennis, and their friends Barry and Mary Ann Yow in June 2009. After brainstorming about a hundred names for the business, Mary Ann joked that they would agree on a name “when pigs fly.” The sentiment stuck. Entrées include pizzas and sandwiches, and Gallimore’s cheesecakes — which she taught herself to make when her son requested one for his birthday — almost always sell out.

Hamilton’s Steakhouse. Inspired by the popular musical Hamilton, the Mackey family took their “shot” at fine dining in a casual atmosphere and opened this cozy restaurant in 2017. All of the steaks have been aged for more than 40 days; Gallimore recommends the crab cakes, too. The restaurant also offers Sunday brunch, including a tasty Bloody Mary topped with a jumbo shrimp.

Cantina Taco Loco. The lively, colorful atmosphere of this restaurant spills out of garage-style doors and onto Sunset Avenue, beckoning passersby to stop in and order a plate of authentic Mexican fare. Tortillas are homemade, and popular offerings include the Hawaiian tacos — filled with rib eye, pineapple, queso fresco, and chipotle sauce — and the organic margarita, mixed with freshly squeezed orange and lime juices.

Doris and Don Simmons share their love of classic Southern dishes — like fried chicken, collards, and cornbread — at Magnolia 23. photograph by Stacey Van Berkel

Magnolia 23. Head Chef Don Simmons began sharing his love of Southern food while tailgating at the University of North Carolina at Chapel Hill, his daughters’ alma mater. His food became so popular that he opened Magnolia 23 on South Fayetteville Street in 2009. “His fried chicken and macaroni and cheese are to die for,” Gallimore says. “And Don is a really great guy, too.”

The Table. The chandelier, made with glass milk bottles, is the focal point of this bakery, coffee shop, and restaurant. Located in the 1925 office building that was once connected to Cranford Hosiery Mill, this airy, farmhouse-inspired space is an example of how Asheboro “refurbishes our buildings instead of tearing them down,” Gallimore says. All coffee drinks are made with Durham-based Counter Culture Coffee beans.

Central Bakery. Established in 1945, this downtown staple is known for its scratch-made cakes, cookies, pies, pastries, brownies, and other sweet treats.

Time Square Pizzeria. Don’t want to commit to an entire pie? At Time Square, pizza can be ordered by the slice, and there are plenty of flavors to choose from. Gallimore recommends the grilled chicken Caesar pizza, which is topped with grilled chicken, lettuce, tomato, Caesar dressing, and Parmesan cheese.

Nannie Mae’s Café & Bakery. The owners of this bakery searched across the state for the right place to set up shop. Downtown Asheboro turned out to be the perfect place. “They make huge cinnamon rolls that are to die for,” Gallimore says. Oatmeal cream pies, macarons, quiches, and other sweet and savory goodies are also on the menu.

At Harper Jewel Boutique, owner Brittiany Byrd offers a selection of trendy clothes and accessories.  photograph by Stacey Van Berkel

Shop

Harper Jewel Boutique. Brittiany Byrd left her full-time job as a nurse to open this women’s clothing boutique, named after her daughter, in March 2021. The shop features a selection of trendy, bohemian-style dresses, shoes, graphic T-shirts, hats, handbags, and Lacole jewelry, handmade in Asheboro by Kailey Walker.

Randolph Arts Guild. This nonprofit has worked with community organizations to provide arts programming to Randolph County residents for more than 50 years. The brick-and-mortar store displays the work of about 50 artists, including local cartoonist and Mad magazine contributor Rich Powell. The guild’s art shows, held on the first Tuesday of every month (except January and July, when they are on the second Tuesday), are a great opportunity to meet artists and view new work.

Minkology. “They have everything from furniture to jewelry to clothes to candles,” Gallimore says. “And they’re convenient. If I need to run in and buy someone a little something, I know I can find something there.” In addition to a variety of home decor and specialty gift items, customers can sign up for workshops on painting, waxing, and detailing chairs and cabinet doors using a special mineral-based paint that the store sells.

Collector’s Antique Mall. Established in 1993 in the former B.C. Moore department store, this 35,000-square-foot, three-story store displays a wide range of well-organized antiques in every corner. This time of year, the ceramic Christmas trees in white and shades of green — some with multicolored lights, some with all red lights — are a nostalgic sight in a front window. The shop’s selection of vintage glass and Hallmark ornaments and houses from the discontinued Department 56 collection also make great gifts.

Sip a local beer and gather with family and friends at Four Saints Brewing Company. photograph by Stacey Van Berkel

Drink

Four Saints Brewing Company. Named for four patron saints of beer brewing, this brewery is a true downtown gathering place. Customers can usually find a fun event taking place, from weekly music bingo and trivia to seasonal events like this year’s inaugural Christmas Bake-Off. There are plenty of opportunities to support the community, including the annual Mug Club auction for local charities, where customers bid on Seagrove pottery mugs to use whenever they visit.

The Black Lantern Tea Room & Bakery. Glowing lanterns, green velvet chairs, and dark wood accents provide a cozy setting for customers to enjoy a full-service tea; soups, salads, and sandwiches; or baked goods. “They have great desserts and savory pastries,” Gallimore says. More than 40 custom-blended teas — including a seasonal Christmas blend — are available hot or iced alongside other treats like chocolate peppermint macarons.

Stay the night at Lawyers’ Row Loft in downtown Asheboro. photograph by Stacey Van Berkel

Stay

Lawyers’ Row Loft. This tastefully furnished one-bedroom, one-bathroom Airbnb in the historic Lawyers’ Row district is run by Asheboro native Christie Luckenbach. Located within walking distance of all of the downtown businesses and just a 15-minute drive from the North Carolina Zoo, the loft is a great base for exploring the area.