Side Saddle is Back!

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PC: TPH Intern Irene Powlick

While side saddle was de rigueur for lady riders until just over a century ago, interest has waxed and waned for decades. In the show world, only a few big mid-Atlantic shows like Devon, Pennsylvania National and Upperville continue to offer a division every year. Yet, side saddle riding has been making a gentle comeback for a decade, and now is back in a big way. The resurgence is evident not only at shows, but also fox hunting and timber racing. Yes, women stay out for hours at a time following hounds and race over timber jumps while riding side saddle. It is like helicopter skiing instead of just taking the chairlift!


Before side saddles came into existence, riding was considered unladylike, to say the least, and impractical. Modesty ruled the day. No woman should have her legs apart in public, even atop a horse. So, women rode “aside” while men rode “astride.” Women dressed in full-length, heavy dresses. The first side saddle was designed in the late 14th century with the woman literally sitting sideways with her feet on a little platform. A saddle with one stirrup on the left with the right leg swung over a pommel, was designed in the 16th century, apparently at Catherine de Medici’s behest. The double pommel, to better secure the right leg, came in the 1830s. This addition allowed jumping, galloping, and participation in sport. The side saddle riding style we see today has not changed since the Victorian era. When safety finally took precedence, britches were allowed to be worn under an overskirt or apron. With the suffragette movement in the early 20th century, women began to break boundaries by riding astride. Finally, by the ‘30s, it was socially acceptable. But, riding aside never faded away completely.

Sue Sisco of Aiken, SC, a long-time hunter rider and trainer, began showing side saddle in 1980 without any premeditation. A friend asked her to show her horse in the Side Saddle division for the season. Undaunted, Sisco agreed even though she had never ridden aside. No problem. Her friend gave her instruction and loaned her a saddle and a habit. Sisco went to some local shows and then straight to Devon where, to her great surprise, she was successful enough to qualify for the National Horse Show at Madison Square Garden. “It was a big deal to qualify for the Garden. The bigger show stables would pull out their best moving horse, put a lady on it at Harrisburg or Devon to show side saddle and qualify for the Garden,” she says. That first year she was “star-struck and overwhelmed,” and was out of the ribbons. In her second year at the National, she was thrilled to get a second. The next year Lisa Frankel asked her to jump her horse, Ricochet, in the division and Lisa would do the hack. Three’s a charm and Ricochet was champion. Sisco rode him for the rest of his long career to four tri-colors at Devon and five at the Garden. She also had great success with Ante Up, owned by Victoria Clavan and trained by Patty Heuckeroth. They were Side Saddle Champions once at the Pennsylvania National and four times at Upperville. “What attracts me to side saddle riding is it’s so traditional. And, if you have a really nice horse, it makes them look even better.”


The 1980s were a heyday of the sport. There were enough ladies showing to have two sections at the big shows, but the numbers dwindled when the National Horse Show moved to the Meadowlands and the prestige of the Garden was gone. By this time, Sisco was coaching side saddle, as well as riding. She and her students kept showing, so the division wouldn’t disappear. Ultimately, the numbers began to rise, especially in Zones 2 and 3. No matter how small, the side saddle classes never lost their popularity with the crowds.


Anne Moss, of Unionville, PA, remembers the day she realized she was just as comfortable riding aside as she was astride, and has not looked back. Since she found an antique habit and Western side saddle in an antique store at age 15, her fantasy was to foxhunt side saddle. To date, she has done that and so much more. She has ridden Fourth Level dressage aside, ridden Western side saddle in parades in period costumes, ridden in Civil War re-enactments side saddle, and coached all levels from beginners to advanced side saddle riders.

After taking many lessons with renowned English side saddle trainer, Roger Philpot, the fantasy came true. For six glorious seasons, Moss hunted a horse named Helium aside. “He was the world’s best hunt horse. He was like riding a catcher’s mitt. Where ever I was, he was under me.” When asked how scary it is to hunt aside, she says, “It is roller coaster fun. It’s a rush and a grin that lasts a week.”


A beginner, Moss says, learns quickly that riding aside takes a lot of conditioning and fitness. It comes down to time in the side saddle, strengthening the abs and the legs to hold the position. But, before a beginner gets on, they must have the right horse and a well-balanced, proper fitting saddle. The horse should respond to a verbal “whoa,” know some neck reining, and have a smooth trot for all the sitting. And, Moss says, “Spookers are not invited to the side saddle party.” She begins by demonstrating correct position at a walk, trot and canter. If you have ridden astride, sidesaddle is almost counter intuitive. Riding with your right leg swung to the left, you don’t put weight on your left seat bone or in your left heel, or the saddle will lean left. You are twisted left, but your right shoulder is back so you appear straight. Rather than riding with your hands, you ride with your seat. “I teach the safety grip. Your purchase is with your right leg. You swing it over and press it against their shoulder. Your left leg comes up to the other pommel, too. You grip hard with your knees and twist right and you can stay stuck on pretty well. You hammer on their equitation because if they’re not in balance, they won’t be comfortable.”


PC: TPH Intern Irene Powlick

Beginners always learn to canter to the right. Cantering on the left lead tends to spin the rider left. “It’s crucial to teach that while you are twisted left, your right shoulder must stay back. Going left is difficult because only your nose can point left, not your shoulder. It’s a patting your head, rubbing your tummy thing. You have to practice. Getting out of the ring is important because turning is always problematic. Hacking makes you stronger so you find your glue. But, once you’re no longer a beginner and find your balance, you’re not so over-twisted. You have a huge seat aid in a side saddle. So, teaching that just sitting up and tightening your right leg creates a strong half-halt is empowering. It’s really all seat. You can balance your horse with your seat. You’re sitting about six inches behind where you’d be sitting astride, so any adjustment you make with your weight, they hear loud and clear.”


Dr. Cindy Buchanan, also from Unionville, and a protégé of both Anne Moss and Sue Sisco, shows, plays polo, events and foxhunts. She took up riding aside about 20 years ago. She says, “You have to do it when you have the right horse, one you know you can trust jumping. You need a smooth jumper – the opposite of what the show jumpers are looking for. You don’t want them to crack their back; you want them to jump flat.”


PC: TPH Intern Irene Powlick

Although Buchanan has hunted aside, her focus has been on the show ring. She has collected her share of blues in the Side Saddle division, as well as winning the Hunt Teams and the Family Class at Devon. Buchanan’s daughters Audrey and Maggie, now 16 and 13, started young, each making their side saddle debut in the leadline class, wearing perfect traditional mini-habits. Maggie won the coveted Devon blue when it was her turn, no small feat in an enormous class of adorable children on ponies. Their family made quite the picture in the Devon Family Class with mother and daughters aside. They won four times in a crowded field and opted not to try to retire the trophy. Buchanan admits, when turnout is as critical as performance, it is quite an ordeal preparing three riders, their horses and tack for side saddle, as well as her husband and father-in-law riding astride. Phew. On the me night, she also rode as part of a side saddle Hunt Team, winning one year and third the next.


Side saddles and bespoke habits from generations ago have been passed down and reworked for today’s riders. A relative newcomer to side saddle, Stephanie Dowling of Unionville, found her saddle was made in 1928 for an English World War I veteran, whom it’s assumed was an amputee who chose side saddle to continue riding.

PC: TPH Intern Irene Powlick

Dowling, a former professional Whipper-in for Mr. Stewart’s Cheshire Foxhounds, took up side saddle a year ago when Susan Oakes, an Irish side saddle phenom, came to Unionville to race in the first Cheshire Point-to-Point Side Saddle Race. With great confidence, Oakes put her saddle on Dowling’s hunt horse Fort Henry and blew the rest of the field away on race day. While in the area, Oakes offered a teaching clinic. Oakes encouraged Dowling to pursue the sport and before long she was hooked. Dowling took to the Hunt Field this past winter. “It was important to me to be able to hunt as I do astride, as a thruster up front. I wanted to be safe and cautious, but I didn’t want it to be a costume show. I wanted to be able to hunt First Flight.” In Cheshire’s past, there were several notable side saddle riders whose stories have come to light with the sport’s recent boom. Key to Dowling’s efforts was her determination to honor the legacies of those hard-riding Cheshire women, to make them proud. “Before I knew it I was in First Flight. I just had to do it, I had the horse and the best way to learn was hunting. Turning in the woods and jumping around other people forced my muscles to react to stay on so much better than riding in a ring.” Her goal was to hunt First Flight with Cheshire, Elkridge Harford and Greenspring Valley Hunts – the big three in hunting over timber fences. Dowling’s next goal is to race aside over timber to qualify for the legendary Dianas of the Chase Cup in Ireland. She hopes to cross that off her list by finishing in the top three at her first race at Willowdale Steeplechase on Mother’s Day. Side saddle races first appeared on race cards last year and are now featured at several race meets in Pennsylvania, Maryland and Virginia.


All those who ride side saddle seem to agree, the effort to retrain your brain and body and to equip your horse and yourself properly is formidable. With steely-jawed determination, a nod to tradition, and a wink of fun, these women riders chase the challenges of riding aside.