As Keri Kampsen walked into client Laura Cramer’s tack room in Middleburg, Virginia, and discovered the collection of side-saddles before her, an idea sparked. Why shouldn’t she give it a try?

“It was an impulse,” Kampsen said. “The opportunity arose, and I kind of just thought I’d go with it!”

Kampsen, a professional who runs her business out of her own Two Goals Farm in Wellington, Florida, had been riding and training Cramer’s horses for the hunter derbies, but the six side-saddles on the wall of her client’s tack room were a surprise. “Most people don’t know I have side-saddle in my past,” said Cramer, who used to foxhunt and show aside, although she’s now stopped riding completely.

“I rode both, but particularly as a child growing up, I remember going to Madison Square Garden [in New York City] and looking at those beautiful horses and ladies riding side-saddle and just being in awe of them,” Cramer said. “And 25 years ago, my husband Joe brought home a horse. And when he dropped the ramp to the trailer, and she looked out the door, I said, ‘That’s my side-saddle horse,’ and she was national champion. She was wonderful.”

So Kampsen asked Cramer if she’d be game to teach a rookie the ropes.

Keri Kampsen tacked up derby mount Take Two to compete in the ladies side-saddle division at the Loudoun Benefit Horse Show. All photos courtesy of Keri Kampsen.

And Kampsen added another challenge to the mix: She didn’t want to attempt this adventure on a made side-saddle mount. Instead she tacked up derby horse Take Two and young hunter Pebble Beach. “Both the ones I did it on were 7 and had never had a side-saddle on them before, and they were very, very good about it,” said Kampsen.

Initially Kampsen was concerned whether her horses would understand the new tack and aids, but her mentor wasn’t stressed. “I said, ‘Trust me, he will,’ ” Cramer said with a laugh.

In her 30 years of riding side-saddle, she’s only ever come across one horse that didn’t want to play. “They respond to it immediately,” said Cramer. “A well-trained horse picks it up easily.”

A naturally competitive person, Kampsen didn’t stop at just taking a few lessons; she entered the ladies side-saddle division at the Loudoun Benefit Horse Show, held June 13-17 in Upperville, Virginia, two weeks later. In a stroke of luck, Kampsen was able to borrow all of Cramer’s habit, right down to her boots.

Kampsen was only able to practice a few times before competing, but she proved that her horsemanship skills transferred outside of the hunter ring. “She was the perfect student,” Cramer said. “Rarely did I have to say anything twice.”

Kramer didn’t even coach Kampsen ringside. “She’s an excellent horseman, so her ability translated to side-saddle perfectly,” Cramer said.

Keri Kampsen and Take Two won the side-saddle under saddle at the Loudoun Benefit Horse Show.

Take Two, a Dutch Warmblood (Cabachon—Catalina N), took to side-saddle like he’d done it a million times, winning the flat and placing third in the hack to tie for the reserve championship in the division at Loudoun.

Kampsen did opt to skip the over fences class, although the hack had two jumps in it.

“I would have to practice a little bit more than the three times I did to feel really comfortable jumping,” Kampsen admitted. “They were like, ‘Do you want to practice more?’ and I said, ‘No I’m just going to wing it!’

“It was amazing how challenging it was to jump a jump like that,” Kampsen added. “I don’t know how they hunt [side-saddle].”

Cramer had been considering getting rid of her side-saddles because she no longer used them, but Kampsen’s interest in the discipline has rekindled her love for it. “It [was] wonderful to see a rider of her quality, and her horse was of such quality too. It brought a touch of class, as far as I’m concerned, to the division,” said Cramer. “It was a beautiful sight to watch.”

Kampsen isn’t planning to swap out her show gear for a side-saddle and smock any time soon, but she enjoyed the new experience and the challenges that came with it.

“It’s definitely something I would try again,” said Kampsen. “It was amazing.”