Horse-Drawn Carriages Bring the Holidays to Middleburg
Written by Bill Kent | Photos by Sherri Holdridge
“Are the horses real?”
Once or twice a year, carriage driver Kelly Smith hears this question from a child about to take their first carriage ride. “When kids see the horses, even if it isn’t for the first time, their eyes light up. I tell them the horses are not only real, but they have names and are meetable and petable,” she says. “Then, if the parents permit, I take the kids up to the horses and introduce them.”
As she brings the kids around the four-seater carriage to visit the two Haflinger horses, Al and Bo, she glances at the kids to make sure no one is holding, or hiding, a dried fruit or candy bar. Smith treats Al and Bo to granola bars and apple wafers only at the end of the day. “When I do a wedding, I tell the bride to hold the floral bouquet close, or the horses might think it’s a snack,” she adds.
Smith’s ability to “watch and listen in all directions at once” has been honed for more than 20 years as a carriage driver for Front Royal’s Shenandoah Carriage Company. After starting as a trainee in 2003 and advancing to groom and driver in 2005, Smith bought the company in 2017.
With Middleburg now at its holiday season peak, this is the first year that Shenandoah Carriage will be providing Middleburg’s winter carriage service. Throughout December, Smith and fellow carriage driver Corrine Rohrbaugh will take up to four people on 15-minute carriage rides down Washington Street with Al and Bo or fellow Haflingers Rusty and Dusty. The carriages board in front of the Middleburg Museum at 12 N. Madison Street.
The job was previously done by Harmon’s Carriages and Training of Brandy Station, which was, until the retirement of Scott and Sue Harmon, Hunt Country’s largest carriage company. The couple had taken the reins from Scott’s mother, Midge, after her passing. Linda Winder, who with her late husband, Art, founded Shenandoah Carriage, admires the Harmons’ 46-year run. “They were the biggest carriage company in Virginia and were very well respected,” says Winder, who remains Shenandoah’s office manager. “When we got started in 2000, Midge Harmon referred many jobs to us. She was a very kind-hearted, wonderful person.”
Though they’re new to the Middleburg holiday carriage circuit, Smith and Rohrbaugh know the town well, having featured in numerous weddings here in addition to working with the Salamander Resort and appearing in Middleburg’s Christmas parade, where Rohrbaugh once prevented one of her horses from taking a nibble out of the costumed Grinch marching just ahead.
“As soon as the Grinch saw what was going on, he interacted with us and it became part of the parade. Honestly, there are so many times I love this job,” Rohrbaugh says.
She continues, “Though the horses work together, to me, they’re all different, with different personalities. Some like to put on a show. Others are quite serious about what they’re doing. What they all love is the attention they get, even when they’re not moving.”
In addition to weddings, parades, and holiday carriage rides, Shenandoah also does pro bono work for charitable foundations, some of which provide disadvantaged and special needs children with their first contact with horses. “We get children who have never been up close to a horse, and they are simply in awe,” Smith recalls. “The horses sense that and want to show the kids that they are as special and wonderful as the kids feel they are.”
One such foundation, a Stephens City branch of the national charity Personal Ponies, was what first inspired Art and Linda Winder to get into the carriage business. “This is not, and never has been, something you do for the money,” Linda says. “You do it for the joy it brings people.”
The company has also offered ghostly Halloween hayrides, driven through county fairs and suburban neighborhoods, visited assisted living facilities, featured at birthday parties, and delivered numerous Santas to shopping malls.
Driving visitors through Middleburg is certainly enjoyable, Smith adds, but it isn’t always peaceful. “We’re constantly training and retraining the horses to keep them familiar with public places and contact with people. So I’m always thinking 20 steps ahead for anything that could make a loud noise, jut in front, or surprise them in any way.”
Just seeing a carriage can raise holiday spirits. John Schwarzman, vice president of Sales Up, has Shenandoah’s horses and carriages, with Santa Claus featured prominently in the back seat, bring Christmas cheer to each of his company’s four shopping centers in Northern Virginia and one in Maryland.
Shenandoah’s drivers, he says, “are 100% dedicated to safety and customer service. Their staff members are well trained, polite, and responsive, which makes a huge difference when we are out at one of these events with all kinds of people in all kinds of weather. The rides have become a holiday tradition for many families. People are all smiles.”
Schwarzman himself has even taken a ride once, “just for fun.”
On most weekends in the spring and fall, Smith and Rohrbaugh do weddings. “When we’re taking the bride and groom from the church to the reception, or from the reception to their hotel,” Smith says, “I can hear them relaxing, unwinding from all the pressure and excitement. They’re having the first peaceful moment of their married life together.”
That’s when Smith lets the horses go slow. “You want to make those moments last,” she says. ML
Published in the December 2025 issue of Middleburg Life.