As the leadline riders filtered into the main hunter ring at the Upperville Colt & Horse Show in Upperville, Virginia, one youngster stood out in the sea of smartly dressed tots in pint-sized hunt coats. Sydney Pemberton sat proudly decked out in a traditional side-saddle habit complete with double reins on her steady mount.

A few minutes later, the 2-year-old Pemberton exited the ring with a blue ribbon fluttering from her pony’s bridle. The idea for the young child to compete side-saddle was spurred by family friend Devon Zebrovious, who is an accomplished side-saddle rider herself. It was meant to be a one-time thing, but Pemberton’s parents, John and Sarah Pemberton, discovered it provided a good way to pony Sydney out on trails, so they continued until her legs were long enough to comfortably ride astride. That one horse show, however, morphed into a vigorous passion.

After an introduction to side-saddle at a young age, 9-year-old Sydney Pemberton prefers it over riding astride. Middleburg Photo

Sydney, of Middleburg, Virginia, tried riding astride as she got older, but she wasn’t as comfortable with it.

“She had a couple big falls astride, and she was like, ‘I don’t want to do this anymore,’ ” said Sarah. “We did six months at the barn where she just wanted to groom, so we went and groomed, and we were over at Mrs. Devon’s one day, and she was like, ‘Maybe I just want to ride side-saddle all the time.’ We were just like, ‘OK, whatever it takes if you want to get back on the ponies.’ ”

And Sydney’s stuck with riding side-saddle ever since. She does occasionally ride astride or bareback, but side-saddle is her preference.

“It’s very comfortable, and then I don’t have to post when I trot,” said Sydney, now 9. “It’s very easy.”

Sydney’s partner in crime is Mary Elaine Boland’s 12-year-old Welsh-cross mare Lynden’s Sadie Hawkins (Shenandoah Cracker Jack—Dance With Me). “Sadie” did a little bit of showing with Boland in the large pony hunters, and the mare showed at Upperville in 2017 with Sydney in the walk-trot (aside, of course), but her true calling is out in the hunt field. When Sydney first started riding the mare, she’d never been ridden aside.

“It was kind of weird because she kept scooting over to the side trying to see where my leg was because she wasn’t used to no leg on one side,” said Sydney.

But once Sadie got used to the idea, she took to it quickly. These days you’re likely to find Sydney and Sadie gamely galloping in the second flight when they hunt with the Middleburg and Orange County hunts in Virginia.

Sydney wants to do everything her riding mentor does, including riding in side-saddle races. But since she’s not old enough yet, this March she entered the Piedmont Fox Hounds Point-To-Point pony races aside.

“I was terrified, but she was just rolling along, her and that pony, just trucking,” said Sarah. “It was great for them—huge confidence booster for all of them. She had the best time. Nothing fazes that kid, and I hope that stays with her for a long time.”

This article appeared in the July 6-16, 2018, issue of The Chronicle of the Horse.

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