Kathy Montgomery Gregory doesn’t admit that her skill with a pen comes naturally to her, at least not on the record, but she loves working with pen and ink. Maybe you’ve seen her work embellishing Main Street, or she’s the speed walking and fast-talking friend who exercises your dogs. 

Gregory is many things for different people, and she defines herself by who she has met. It starts in town, thanks to a rich history with Fauquier through her parents.

Fairfax to Fauquier

The Montgomery family used to be “city-slickers” situated in Fairfax before her parents craved the country enough to buy a 123-acre farm in the 60s. Kathy took to the horses and cows, plus some fox hunting. She didn’t have a habit of drawing then, she would give her pieces as gifts, but she was raised in an art-embracing home.

“My parents were big in the community, they called them the Musical Montgomeries because my dad played piano and my mom was a singer,” she said. Kathy’s father owned Montgomery Shade & Awning in town. “I feel like he taught me how to be in the community, to give back,” she said.

Richmond realizations

Once she graduated high school in Warrenton in 1971, she moved down to Richmond and spent some time as a secretary where she met Gene, her husband. He caught her attention with his mustache and kept it to this day (her attention, that is). 

She also worked as a hairstylist, fitness instructor, and dog walker. “You learn from everything you do. I did a lot of different things and met so many great people,” Gregory said.

One day she noticed the Virginia Museum of Fine Arts was going to host an art show accepting public submissions. Since she would always gift her art at the time, she asked her brother Rob for the Christmas gift she had given him–a pen and ink drawing of a raccoon.

“I put it in the show, and I got second place,” she exclaimed, “I sold it for $40, and in those days, that was big time.” Her smile pervaded her voice as she recalled the memory. She got back into pen and ink following the experience, spending spare time drawing animals, cars, and people.

When one door closes, another opens

When Kathy and Gene moved to North Carolina in the 90s, her drawing faded. After her parents passed away in the early 2000s, they moved back to her family home in Casanova in 2007, off of Rogues Road, and she started Packpower Dog Walking. “I’m known as the fast walker. I’ve still got it,” she laughed.

About a decade later her doctor identified a melanoma on her leg. They quickly followed up with surgery to remove it, but recovery meant no dog walking for a while. Kathy’s friend and neighbor, fellow artist Greg Huddleston, encouraged her to spend just 10 minutes a day on her art. Days of 10 minutes turned into weeks of 20 hours of creating art with pen and ink and soft pastels.

Kathy drew the dogs she would walk and vintage cars and entrepreneurs that ornament Warrenton–signing it “Katydidit.” Kathy learned under Jennifer Sims in classes at Stuart Street Atelier until Sims said that Kathy was self-motivated enough without help. Becky Parrish mentored her in personal sessions at Kathy’s house. She set up an art studio in the back room that was her mother’s.

Art in all she does

Kathy said her years of working “with [the] body, how it’s sitting, [and] how it’s leaning” (through her fitness classes) played into how she captured subjects in her art. There’s art is all she has done, including hairdressing. “I could make people look great, and that’s how I feel with my artwork,” she said, “It all kind of comes back to you.”

Hound ‘n Hair owner and all-around aficionado Bob DiNunzio asked Kathy to do some postcards and wound up selling them all. He advised that she own her style, and that’s just what she has done. She usually does pastel and oil pastel then adds linework in pen and ink. For those she knows and comes across, she is inspired to draw for them–including the businesses along Main Street. “I’ve probably done one for every business,” she said.

The people who “drew” her in

It’s all about “the people who touch me,” she said. When Old Town Woodworking owner Steve Bailey’s Great Dane Eris died this year, Kathy did a drawing of her to give to Steve. She captures the essence of subjects in her art, it’s easy to see in the eyes of her drawings. “I can pick out the personality in whatever I do,” she said.

Her pace has slowed a bit to match her clients’ dogs getting older–although some want to go 100 mph while others are slowing down on the leash. She often pauses nowadays, expressing gratitude for everyone she has met.

“You think about what people do for you… they might not think it’s anything. People don’t realize what they do for you,” she said, musing, “What can you do for people? For me, [drawing is] what I do. It might give them a boost where they needed it. I know I need them.”

Her reverence for everyone around her goes deep, that’s what motivates her art and makes her pieces so alive. She concluded, “It’s the people that I meet that make me interesting.

For information on commissions, message Kathy Gregory through her facebook page. 

This article originally published in Warrenton Lifestyle Magazine, July 2022. Read the full issue here

Jaya Patil is a freelance writer for Warrenton Lifestyle Magazine.

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