“A pony walks into a library … ” Is it the foundation of a joke in need of a punch line? The start of a melatonin-induced dream? Or a captivating scene from the National Sporting Library & Museum’s Founders’ Room in Middleburg, Virginia?

The latter, as a pony spent several hours a day standing in the library’s Founders’ Room for the benefit of equine portrait painter Madeleine Bunbury’s interactive demonstrations the week of Oct. 23 among the shiny hardwood floor, old-fashion curtains and historic hunt scenes framed on the walls. 

“I’ve been coming to Middleburg for the last four years annually; I just come for a month to paint portraits of people’s horses,” said the British painter. “I spoke to Elizabeth von Hassell, who manages and runs the museum, and she came up with this idea just to get people to come and see a real horse. Middleburg is such a horsey town that we thought it would be right up everybody’s street. And then we had to find a pony.”

On that front, von Hassell enlisted decades-long friend Snowden Clarke of Orange Hill Farm, also in Middleburg. 

When von Hassell asked Clarke for a favor, he agreed before learning precisely what she wanted.

“And then she told me what it was. And I said, ‘Well, we’ll make it work,’ ” he recalled.

Clarke, who also works as a realtor for Thomas & Talbot Estate Properties in town, thought of Rooster, a 6-year-old small green pony he purchased a couple months ago to make up and eventually sell. “He’s a beautiful pony, and he’s a great temperament,” Clarke said. He figured the petite equine would suit the indoor assignment best—but he did want to do some practice runs first. 

“It was either him or something a lot bigger,” Clarke said. “I thought, ‘Well, we ought to start out slow,’ so smaller. … We tried him at the house once or twice, thinking we ought to try this out. And he walked right into the house and stood very patiently. So, we gave it a go, and he couldn’t have been better.”

Trailering into town each day, Clarke would unload Rooster and walk him in through the back of the Sporting Library (the front entrance had too many tables and other obstacles for a pony to negotiate). And from 11 a.m. to noon and then for an hour in the afternoon, Rooster stood on rubber mats while Bunbury loaded her brush with paint. Whenever it looked like he needed to go to the bathroom, Clarke ushered him outside to the grass.  

“The pony had to come on the skiddy floor—the polished, wooden floor—and had to slip all the way until it got to his mat, and then he could stand happily on his mat,” Bunbury said. “That was every day for five days.”

Each day Bunbury displayed her artistic methods to people and groups stopping by in person and those tuning in on Facebook live. A Florence, Italy-trained classical artist, she explained her background, including her lifelong affinity for horses and her inspiration, the famed English equine painter George Stubbs, to the audience during the first session. 

“The pressure was on because everyone was watching my every move,” she said. “So, I couldn’t slack, so no breaks.”

While painting in the Sporting Library was different from her day-to-day work, which typically involves private portraiture in settings where one normally expects a horse, the experience thrilled her. 

“It’s just exciting to see how many other people are interested in horse painting,” she said. “I love being able to share my passion, which is painting, and that people can come and be just as enthusiastic as me.

“I asked the crowd: ‘What do you think? Is that too big? Too small?’ ” she added. “And I had input from the crowd—people who weren’t artists helping me with the painting. It goes to show, you don’t have to be a trained artist to be able to see and appreciate art and critique it even.”

During the lunch breaks, Rooster’s close encounter with human life continued: He and Clarke ate at local watering holes and walked around Middleburg’s quaint downtown visiting shops. 

“I held him on the streets, and we ate at the Red Horse,” Clarke said. “Another time we sat at the [King Street] Oyster Bar outside, and I held him, and we had lunch. He couldn’t have been sweeter. Of course, he got all his treats, too.

“They stopped me outside of [Another] Blue Moon, and said, ‘Oh, let’s get a picture of him under the sign,’ ” he continued. “Well, he walked straight in. The problem with going in—I thought it would just be in for the picture and out—well there was nowhere to turn him around. So, we kind of had to go all the way around the store.”

After five days, Bunbury finished her portrait of Rooster and donated the painting to the Sporting Library, which auctioned it off, raising $5,000 to support its program fund. And on Oct. 29, Bunbury hosted a Sunday Sketch class for the public to personally take a turn capturing her model. 

Clarke was as captivated by the painting lessons as any other spectator.

“I wish it went for longer,” he said. “I volunteered him: Anywhere Madeleine goes, we can travel. My pony can travel if I can sit that close to watch that canvas transform.

“For me, being able to literally watch from [the first] stroke on this huge, life-sized canvas and then seeing the last stroke—it was an incredible experience,” he added. “It was magical to see that. And then also to be so close to see the mixing of the colors, and the different brushes used, I couldn’t have had a closer look at what was going on.”

Though Bunbury loved the interactions and feedback from the public—some of whom dropped in every day to see the progress—her favorite note came from Rooster himself. 

“The best part of the painting process was the last day when it was finished: We turned the painting around to face Rooster,” she said. “His head went up, his ears went forward, and he neighed at the painting as if it was a horse. That’s the greatest compliment, when the horse recognizes it. He came up and tried to sniff at the horse; it made me shiver.”