Upperville, Va.—June 8

The last time Amy Jo Magee showed in the side-saddle division at the Upperville Colt & Horse Show was nearly 20 years ago—back when the Parker Ring, which sits under iconic oak trees in front of a historic grandstand, was all grass.

Things may have changed a bit at the historic show since then, but Magee’s love of riding aside hasn’t.

Showing Last Call, her 6-year-old homebred Hanoverian gelding (Landkoenig—Freya, Flamenco), the 49-year-old rider won the ladies side-saddle hack and the Hermen Greenberg Side Saddle Stake on Saturday to win the ladies’ side-saddle championship. Lauren Apple and Jessica Lampe’s Cheetah Beach earned the reserve championship.

“My heart is just exploding,” said Magee, of Coatesville, Pennsylvania. “And Lauren and I live within 10 miles. We both have a four-hour drive home. This will make that drive home take two seconds! You can’t beat this. It reminds me of the hunt field. It’s so easy. You just sit up, and the trees and the grandstand—I love Devon [Pennsylvania] because it’s my big home show, but I think Upperville’s the most beautiful show.”

Magee has been riding aside for nearly three decades after being inspired watching side-saddle at Devon and spurred on by an accident. 

“When I was 28, I had a horse flip over and shatter my pelvis, and I broke my back. I find it more comfortable,” she said. “Riding astride is more difficult because I don’t have any control of my left leg. In side-saddle, your left leg doesn’t do anything. I love riding side-saddle. I just feel like it’s so elegant, and it makes me want to sit up and smile because I enjoy it so much.”

“Blue” is her fifth homebred. One of his full sisters was Magee’s previous side-saddle horse, and she competed up to the 3’6” performance hunters and in national hunter derbies aside. She’s also competed in eventing aside, making it to the U.S. Eventing Association American Eventing Championships (North Carolina) in 2005 at training level.

Blue fox hunts with a side-saddle as well. “I wasn’t sure he was ready for side-saddle, but in the fall, I took him hunting with Radnor [Pennsylvania] as our first big [side-saddle] outing, and hunted through the winter,” Magee said. “He is a complete gentleman when I’m aside. He knows when I put that side saddle on, and he just does his job. He is the quintessential ladies’ horse.”

The pair also won the side-saddle championship at Devon in May.

“This year is my return to showing,” said Magee, who hadn’t been in the ring in any capacity since 2019. “Both my children are old enough that I can go to an overnight stay. I said, ‘You know what? This year I’m going to give it a go.’ The kids are a little older now finally, so I can get back to what mom likes to do.”

In addition to her passion for riding, Magee is handy with a sewing machine, and started a business, Black Diamond Designs, where she makes side-saddle habits and makes and repairs traditional side-saddle tack. She made the habit that reserve champion Apple wore at Upperville.

Another Upperville competitor, Blair Snively, also benefitted from Magee’s expertise.

“[She] messaged me two months ago and asked for a sewn-in bridle [for the appointments class], and I said, ‘Mail me your bit, and I’ll sew it in for you.’ I’m happy to say, ‘This is what you need for your appointments, this is what you’re looking for.’ I want people here. I think people come out to watch this because they love the elegance of it.”

Magee, who trains with Troy Hendricks at Kimber-View Stables, hopes to keep the elegant tradition of side-saddle alive through her business and by mentoring riders who need help.

“We do have these peaks and troughs. It goes up and down,” she said of side-saddle show entries. “I know the hard part is finding the equipment, but I tell ladies, if you want to do it, reach out to one of us who are out there doing it, and we will help you because this is where it started. This is what ladies did. I think it’s critical for us to keep that alive.”

For more images from Saturday at Upperville, read on.