​​today -- an English style Martin & Martin and a Western-style saddle made by Lillian Chaudhary – Basile estimates having purchased more than 15 over the years. But it wasn’t until 2001 that she bought a sidesaddle that fit her and her horse and began competing.

“The saddles I found at the auction were Victorian era and apparently women were tiny, so if they were sound enough to ride in, only a child would fit,” Basile said.

Sidesaddle, or riding aside, may have started as an aristocratic style to allow women to be ladylike while on horseback. Princess Anne of Bohemia, who rode aside while traveling across Europe to marry England’s King Richard II in 1382, is credited with popularizing the style in England.

Today’s sidesaddle riders, however, ride for the

thrill of the challenge on the trail, over fences,

in the show ring and purely for the fun of it.

Any breed of horse can be taught to be ridden

sidesaddle. Maggie Herlensky, the American

Sidesaddle Association president, has ridden

both draft horses and light breeds sidesaddle.

“As long as the breed rules don’t specifically

prohibit sidesaddle you can compete in it for

classes that are judged on the horse,” Herlensky

said. “Saddlebreds, Arabians and Morgans offer

classes.” The American Quarter Horse Association,

for one, forbids riders from showing sidesaddle,

although stock breeds can certainly be ridden

aside informally.

The New York State Fair Horse Show offered

all-breeds sidesaddle classes as did the Empire State Arabian Horse Show, and indeed the options are limitless when it comes to what a rider can do aside rather than astride.

Riders can compete in steeplechases – the Genesee Valley Hunt Races will feature a cross-country sidesaddle race this October – flat races, drill teams, sanctioned United States Eventing Association competitions, parades, endurance rides, pleasure shows and more.

A quiet, willing horse and an interested rider is all it takes to get started. Herlensky has worked with riders whose horses who knew the basics – how to turn and stop – all the way up through Prix St. Georges dressage horses (those four-legged magicians with the extended trot, canter half-pass and other fancy footwork).

“The horse really only needs to know how to direct or neck rein and respond to whoa. The less leg cues a horse understands the better to start off – so they’re not waiting for the right leg cue,” Herlensky said. “The biggest thing is that the horse must be pretty quiet to mount and dismount. That’s the hardest part. There’s no graceful way of getting on and off.”

Regardless of the rider’s current discipline, there’s a sidesaddle that’s similar. There are Western, English and hybrid style saddles to choose from. When Bloomville rider Amy Morris saw a Western sidesaddle she was intrigued, especially because it is touted as more comfortable for people with joint pain.

“I was intimidated at first, but I met people online who were supportive and shared info. When you find a group of friendly people as a beginner it’s easy to ask for more,” Morris said.

Comfort is the reason that Herlensky

began riding sidesaddle as a teenager.

She suffered from joint pain and her

mother read an article in Western

Horseman touting the comfort of

riding sidesaddle. She’s ridden

sidesaddle ever since. She has logged

3,000 miles participating in endurance

rides riding aside and has ridden in

Presidential Inauguration parades.

But just because of its history as a

ladylike way to ride, don’t think there’s

nothing more to riding sidesaddle

than sitting sideways. Sidesaddles have

a curved pommel that cradles the

rider’s right leg. In the 1830s, a

revolutionary second pommel – also

called the leaping head – was added for the left leg, giving riders more stability and control and allowing less modest equestrian pursuits like galloping and going over fences.

The biggest challenge to getting started in sidesaddle is finding a saddle. Fit, riders say, is more important in sidesaddle than with any other discipline. A tree that is too narrow or wide will roll off the horse. And if the seat doesn’t fit the rider precisely, she will feel as if she’s falling off.

“Even if it’s only a half-inch off, it won’t ride right,” Herlensky said.

Measuring a rider for a sidesaddle is slightly different than astride saddles. The seat size is based on the length of the rider’s thigh and not the size of their rear. To get a measurement, the rider sits on a table or bench with the edge at the bend of their knee. Then measurements are taken to the back of their backside and an inch is added. Herlensky is 5’ 8” and rides in a 23” sidesaddle seat.

Sidesaddles aren’t as plentiful as other style seats making well-made saddles pricey. Before investing, Herlensky encourages interested riders to reach out to her – she’s at
maggieszoo@horizonview.com  -- or other instructors for advice. She often recommends buying a used saddle even if it needs basic repairs and flocking to fit.

“Used sidesaddles have a sweet spot where the rider sat, but it might not match up with you so it’s important to spend time to find the right one,” she said.

As an ambassador of the discipline, Herlensky is a clinician and instructor and invites riders to participate in club activities. Thanks to the internet and social media, finding a group of enthusiasts has never been easier.

“Our unofficial motto is: ‘You can show up in your underwear,’” she said. “We’ll have a horse, the equipment and all you need to ride. Most of our riders learn in the parking lot before their first parade.”


Story by Katie Navarra

Decades before the televisions series Downton Abbey glamourized women riding aside, Julie Basile was fascinated by sidesaddles. The décor in her childhood home included four Victorian paintings, all of ladies riding sidesaddle. She pored over books that featured photos of women riding sidesaddle.

“I was mesmerized,” said Basile, who calls Buffalo home. “I loved the elegance, and it was different from anything I would see at local horse shows and events.”On the third Saturday of each month, she attended the Sherman Livestock Auction where used sidesaddles often surfaced for sale in the mid-1980s. Although she only owns two 


RIDING ASIDE: Sidesaddle riders love the sport for the challenge on the trail, over fences, in the show ring and purely for the fun of it

​ ​​New York Horse magazine 


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