Racing Aside: Scenes From the Cheshire Point to Point Sidesaddle Race

Susan Oakes began riding sidesaddle when she was four years old. She was the ringer brought in from Ireland to run in the first inaugural Mrs. Miles Valentine Memorial, a sidesaddle race for ladies last Sunday in Unionville, PA.

She felt charmed when she was loaned an Irish timber horse for the Cheshire Point to Point. Fort Henry, owned and trained by Stephanie Boyer, had never been ridden aside, but Susan took him out a couple of times before the race using her 130 year old sidesaddle. She said that with her good balance and his willingness, the transition was smooth.

Spectators stood at the top of the hill and looked down through the leafless trees to catch peeps of the thirteen ladies riding astride.

It seemed to be the modus operandi to cross the finish line with an arm extended upward punching the sky in concert with a wild primal call.

As they came around the first corner and emerged into view Oakes and Mary Musheno were neck and neck at the front of the pack. Shifting into fifth gear, Oakes decisively pulled away from the throng. Musheno challenged Oakes one more time briefly, but coming into the finish it was all Oakes, wearing an expression of fierceness and pure joy.

L-R: Susan Oakes and Fort Henry (IRE) and Mary Musheno and Lucky to Have Him.

It looked terrifying to the spectators. Many a rider took air over the fences, like Cathi Groves and “Figure It Out”:

Cathy Groves and Figure It Out, followed by Becca Barker and Shiloh.

The course circled up and down the steep hills of Unionville and included seven 2’6″ fences. The end of the two mile track was up a long, killer hill lined with spectators cheering wildly as the riders streamed by to the finish. The ladies were elegantly attired in riding habits, many of which were vintage. It seemed to be the modus operandi to cross the finish line with an arm extended upward punching the sky in concert with a wild primal call.

Flushed with adrenaline, the ladies enthusiastically shared their stories. Below, Amy Jo Magee gives us a sidesaddle riding tip:

Magee was also awarded the Best Turned Out, which not only included her smart riding habit, but the condition of her horse, cleanliness, condition of her tack and braiding. This award was sponsored by Middy N Me, the maker of beautiful equestrian inspired shirts.

Jenny Kobilinski (below) said that riding the jumps wasn’t the most difficult part of the race:

Becca Barker clearly didn’t have a lot of fun:

Catching up later with Oakes she, too, gave us a parting pointer on technique: she leans forward into the jump so as not to get left behind. It’s very different than traditional riding because she is not able to adjust her stride when approaching the fence and she needs to take what is presented to her.

Check out this head cam of Susan Oakes and Fort Henry to experience the closest thing to you riding sidesaddle:

You feel you were there, right?

A painting of Mrs. E. Miles Valentine, painted in 1966, hangs nearby in the Brandywine Museum. She is at rest on her horse riding sidesaddle, beautifully turned out in a grey riding habit and top hat with the hills of Unionville dusted with snow in the background. She might be at a check point while out hunting with Mr. Stewart’s Cheshire Hounds. Her eyes tell you she is confident and strong and her bearing suggests a formidable character. We salute Mrs. Valentine for a great day at the races.

Amy Jo Magee

L-R: Becca Barker Christina Mulqueen Cathi Groves and Amy Jo Magee

Results

The race was sponsored by Middy N Me
1st – Susan Oakes – Fort Henry
2nd -Mary Musheno – Lucky to Have Him
3rd- Bernadette Boland – King of Hearts
4th – Maureen Britell – Tango
5th – Devon Zebrovious – Handsome Is
6th – Sarah O’Halloran – Patrick
7th – Julie Nafe – Madame Belvedere
8th – Jenny Kobilinski – Penny
9th – Amy Jo Magee – Little Lady
10th – Christina Mulqueen -Waffles
11th – Rebecca Barker – Shiloh

The Mrs Miles Valentine Sportsmanship award, donated by Mr. and Mrs, Stephen Groves and voted on by all riders, was awarded to Christina Mulqueen.

This sidesaddle race was the first in a three part series. Coming up on April 17 is the Loudoun Hunt Point to Point followed by the High Hope Steeplechase in Lexington, Kentucky on May 22.