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Paint-splattered easels sit side by side on a pair of wooden tables in the front room of an 87-year-old house near downtown Asheboro. Nikki-Cherry Crofoot walks down the line of workspaces, placing white foam plates in front of each one. Her husband, Andy, follows behind, squirting pools of brown and red acrylic paint onto the platters. “I hope everyone comes ready to have a good time,” Nikki-Cherry says, “and that they aren’t afraid to try something new.”
When she opens the door of The Preppy Possum, her paint-and-sip studio, customers arrive, slip on aprons, and slide onto stools facing each easel. The students — some of them novices, others more experienced artists — have come to paint a holiday scene: a Christmas wreath-laden pickup truck parked in the snow. Not that Asheboro gets massive drifts of the fluffy white stuff too often, but being creative is what makes painting at The Preppy Possum so much fun.
Nikki-Cherry Crofoot loves teaching kids how to paint pets in holiday sweaters, like this Boston terrier in Christmas Pooch. photograph by Jerry Wolford & Scott Muthersbaugh
As she walks about the room, smiling at each student’s work, Nikki-Cherry draws on her years of training and experience in the arts to guide the budding painters through the process of creating beautiful images. After all, she was once a novice herself, just like most of her customers. Nurtured by her maternal grandmother, Nikki-Cherry’s childhood passion for art blossomed into a career. In 2009, she established The Preppy Possum in order to host art classes in local businesses and at community events. Three years later, she and Andy transformed this old Craftsman-style house into a warm, inviting permanent space where she could coax the inner artist out of anyone willing to come in, pick up a paintbrush and a glass of wine, and follow her instructions. “It’s rewarding to watch others create. It’s the most rewarding when they truly get it — when they get that art is a process,” she says. “I love when people are proud of what they’ve created.”
Nikki-Cherry’s own creativity grew from seeds planted on Christmas Day in 1987. She was 5 years old, and her family had gathered for dinner at the home of her namesake grandparents. After finishing off Grandma Cherry’s glazed ham and beef tenderloin, Pawpaw Cherry began handing out presents. Nikki-Cherry tore into the one with her name on it, and found an art set that opened like a briefcase. She marveled at all of the colorful pencils and paints, markers in every hue, and brushes of all sizes. Tucked at the bottom were two thin canvases. “They weren’t expensive kits,” she says with a wistful smile. “But they were filled with magic.”
A longtime collector of Ball jars, Nikki-Cherry uses them to hold her paintbrushes. photograph by Jerry Wolford & Scott Muthersbaugh
She shared an interest in art with her grandmother, who also loved to express herself through colors. With Grandma Cherry’s encouragement, Nikki-Cherry eventually began selling her folksy paintings at local and regional festivals. As she worked her way through the circuit, she noticed that other booths used cute names to draw in customers. She decided to call hers “The Preppy Possum,” because she liked the way the words sounded together, and she soon began working with business owners in downtown Asheboro to offer casual painting classes. When the paint-and-sip trend caught on in the early 2010s, she took the income that she’d earned from her classes and commission work and opened The Preppy Possum’s physical location. Here, she could offer a variety of classes for children as well as for adults who enjoy having a glass of wine while creating art.
Andy signed on to be his wife’s assistant, helping with setup, replenishing paint, repeating Nikki-Cherry’s instructions to students, and doing whatever else was needed to support the business. And the couple’s creative spirit spills well beyond the easels inside The Preppy Possum. The two also take pride in helping make their community more compassionate.
The Preppy Possum was named Employer of the Year for its work with special-needs adults.
When Nikki-Cherry was a child, one of her earliest friends was a little boy with a learning disability. By high school, she was volunteering to assist other kids with special needs. When The Preppy Possum was up and running, she and Andy decided to continue those efforts. They began working with Randolph Vocational Industries, which connects businesses with special-needs adults seeking jobs. That’s how they found Lindsey Pizzola, who helps Nikki-Cherry fold paper towels for The Preppy Possum’s art classes. “We’re the first job Lindsey has ever had, and she’s proud of the work she does with us,” Nikki-Cherry says.
During a 2018 ceremony for National Disability Employment Awareness Month at Asheboro’s Bicentennial Park, the mayor presented The Preppy Possum with the Jim and Audrey Harriman Employer of the Year Award for their work with Lindsey. “The mayor said that numerous people had nominated us,” Nikki- Cherry says. “We were floored.” She also takes art classes into assisted-living communities, schools, and other organizations, expanding her reach well beyond the row of easels at The Preppy Possum.
In 2020, Nikki-Cherry and Andy expanded their reach on a more personal level with the arrival of their daughter, Ruby Fern. Inside The Preppy Possum, the toddler’s soulful hazel eyes sparkle as she watches a bird alight on the front porch glider. She turns, looks back at her mom, and smiles, showing off brand-new teeth. When music blares from the windows of a passing car, Ruby Fern’s little foot begins to move, and she squirms to get down on the floor.
This year, Ruby Fern will likely get an age-appropriate art kit of her own for Christmas, but Nikki-Cherry is quick to note that her daughter seems more interested in music than visual art. “I may have to find toddler dance classes or drum lessons based on the way she gets excited and moves to any kind of music she hears,” Nikki-Cherry says with a chuckle.
Brielle Davis adds the final touches of green to the wreath in her painting Red Truck in the Snow. She’s a Preppy Possum regular, having completed about 40 works there. photograph by Jerry Wolford & Scott Muthersbaugh
Although the paint-and-sip trend has been a boon for The Preppy Possum, Nikki-Cherry says that, in the future, she plans to spend more time on art sessions for children. “They’re better artists,” she says. “They’re not weighed down by the worries and stresses that adults carry with them onto the canvas.”
Nikki-Cherry loves the energy and spirit that kids bring into this old house, and to the classes that she teaches at schools and other community events. She’ll continue to offer adult classes, but as a young mother and a painter who specializes in fun, colorful, and playful works of art, Nikki-Cherry is constantly moving forward, focusing on what makes herself and others happy.
The Preppy Possum
830 South Cox Street
Asheboro, NC 27203
(336) 963-9063
thepreppypossum.com
City Art Room is a full-service public art studio and gallery conveniently located on the second level of The Shoppes at University Place, which offers more than 38 shops and restaurants where you can also eat and knock out your Christmas shopping. This studio provides public and virtual paint-and-sip events.
9009-9 J M Keynes Drive
(980) 500-9149
cityartroom.com
The Dusty Pallet offers instructional paint parties either in-store or at a location of your choosing. Open party attendees can bring tea, coffee, and soft drinks, while at private parties, customers are allotted their choice of beverages.
52 East Main Street
(828) 524-5676
thedustypallet.com
Bring a few friends and your favorite wine, and tap into your creativity at The Tipsy Paintbrush. Sign up for a class or host a private holiday painting party.
321 North Indian Trail Road
(980) 229-5500
thetipsypaintbrush.com
Attend a wine and painting event at Pinot’s Palette for a fun night out or host a private event. Pinot’s tailors its classes to your needs, offering in-person and virtual painting parties. Guests can purchase beer, wine, and cider from the bar.
10410 Moncreiffe Road, Suite 101
(919) 391-0258
pinotspalette.com/briercreek
Wine and Design’s On Wheels program partners with local businesses to provide fun and creative painting parties at a venue of your choosing — including your home. It also offers a range of affordable private and public parties, and painters are encouraged to bring their own wine, beer, and snacks.
1319 Military Cutoff Road
(910) 679-4750
wineanddesign.com/calendar/wilmington-nc
— Rosa Stancil
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