Riding Sidesaddle, Part 1: Learning the Sport


Lady Mary in a scene from Downton Abbey

Jane Smiley’s Horse Country, a piece published last year in the New York Times, describes grass and sky and mist over Virginia and the wide, flat expanse of Maryland – both regaled horse countries. The tiny taste I got while driving through the Adirondack Mountains and experiencing the rich horse culture of Saratoga Springs left me with nothing but good things to say about the eastern United States.

I’m going to hedge a guess, based on what I’ve read and heard from friends, that the horsey culture of the rest of other eastern states is equally valued or perhaps even more potent than what I experienced around Saratoga Springs.  I have a friend from Maryland who tells me I’m missing out, and know folks from Pennsylvania who say there’s nothing better.

But we know what we know and we have to appreciate what we know, and I mainly know Fargo.

Here in the Fargo area, we have wide and flat down par. We also have plenty of sky and a bit of mist every now and then. But one thing we don’t have that the equine-celebrating east coast does is the sidesaddle riding discipline.

Ever watched Downton Abbey? Not going to lie, I haven’t because I don’t really watch TV, but apparently the popular show is triggering a “Lady Mary effect,” leading to an upsurge in the amount of people beginning to ride sidesaddle.

Neat to see the trickle-down effect of pop culture in other sectors of the world. I wasn’t part of that trickle-down effect when I learned to ride side saddle. I was just lucky enough to live with an amazing “Saratoga Mom” for two summers in a row who rides sidesaddle and has a long history with east coast horse culture.

On one of my rare Tuesdays off during the Saratoga race meet, Saratoga Mom Donna loaded me into the car with her sidesaddle and we headed off to the barn where she boards “Java” and “Big,” her two off-track Thoroughbreds.

Learning to ride sidesaddle was one of the coolest experiences of my equestrian career, and I can’t wait to tell you all about it! But first I want to fill you in on the history of my amazing instructor/Saratoga Mom extraordinaire, Donna Vild.

I recently sent Donna an email to ask about her introduction to riding sidesaddle. Her response was “I’m always up for publicizing sidesaddle riding. It was nearly a lost art that Lady Mary managed to bring back nearly single-handedly!”

Donna’s the editor and publisher of the Upstate Horse, an equine publication that serves upstate New York’s horse community. She was introduced to riding side saddle when she attended the Devon Horse Show with a friend in 1991.


Donna and CeCe (Country Christmas) at the Devon Horse Show in 2005. Photo courtesy of Donna Vild

“What a sight!” Donna said. “Forty-five horses and ladies in top hats and habits with everything polished to the nines. I was fascinated.”

Donna began taking lessons from that day’s champion rider, who happened to live near her. She later became a working student in the world of eventing, but made it back into a sidesaddle when an eventing connection gifted her with a saddle and double bridle.

“A trip to Graham Motion’s mother’s shop in Middleburg secured all the odds and ends for the formal class at Devon,” Donna said. “Now it’s even easier with eBay and sidesaddle sites on the internet to find all the appointments.  Back then it was more like being in the right place at the right time. That Mid Atlantic area with the deep foxhunting history is chock full of top hats, hunt whips, sandwich cases, etc. so it was doable without the internet.”

Donna now has two saddles, both of which are from the 1920s (which I think is amazing). So much history, I would love to see everything those saddles have witnessed and experienced over the years!

She’s long used her OTTB’s for sidesaddle, one of which was “CeCe,” or Country Christmas (one of the cutest names ever because it reminds me of a Terry Redlin print of horses pulling sleighs through the snow).

“I had my mare trained for combined training and we just showed her in a Training level frame aside,” Donna said. “We tried to flatten her out like the top show hunters but she was a really round mover and neither of us could pull that ‘flat’ look off very well. We showed sidesaddle on the flat at Devon a number of times between 1999 and 2010.  We were in the low ribbons our last two years on the flat. We also showed at Gladstone at the yearly sidesaddle show there. We were champions in Schooling hunter in 2004, which involved a flat class, a hack class with two jumps and a hunter round. This mare loved to show…”

Now Donna rides Java to Go, or “Java” for short. Java raced on the flat (races with no jumps) in the Midwest for a number of years before starting in races over brush fences (jump races with scrubby sorts of obstacles). He then transitioned to timber races (which are like big wooden fences).

The way Donna describes his jumping ability during his racing career is absolutely beautiful, so I’m going to let her take it from here:

“He was a very careful jumper over timber with an amazing jump – he’d just soar.  He usually ran out front and would gain ground at each fence.  He wasn’t so fast between fences so the pack would typically get closer, then Java would open up more daylight at the next jump.  He jumped a couple of horses into the ground when they tried to go with him but lacked his effortless scope.  I schooled him a few times ahead of his races and he just came off the ground like gravity had let up. The horizon would drop (Oh, we must be in the air!) and then it would come back up where it belonged (Oh, must be back on the ground!). Couldn’t feel the push off the ground nor the hooves hitting the earth.    

“(Java) raced in National Steeplechase Association-sanctioned races from South Carolina to Pennsylvania and in the Mid Atlantic point to points until he was 13,” Donna said. “The Maryland circuit kept their own points and Java was the 2006 Maryland Steeplechase Horse of the Year with Open Timber wins at Marlborough Point-to-Point and the Potomac Hunt Races.  He was well known on the steeplechase circuit.  I used to lead him up and you’d hear “java” “java” “java” “java” all the way around the paddock! He never had a sanctioned win over timber but he always tried hard and made the other horses earn it.

“Java had retired from racing and was hanging out with his still-racing buddies and got pressed into service one year for Gladstone.  I had sent my entries in for my mare and then she developed an abscess that was very slow to clear up.  She wasn’t coming sound so I decided to go see what Java thought of the sidesaddle.  The show offered walk trot for beginner horses so I thought we might be OK. He was lovely with the sidesaddle. (Racehorse trainer) Eddie Graham stopped by and was watching Java go sidesaddle and was so amazed how well he looked, so that kind of sealed the deal. Off we went. He was in the ribbons and generally behaved himself…”

Check back to read about my first time riding sidesaddle on Java in Riding Sidesaddle Part 2: Lady Annise takes a spin.

A BIG THANK YOU to Donna Vild for her help on this blog!

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