March 24, 2016 
There’s not much that seems to intimidate Susan Oakes. The Irish rider is well known for doing things on horseback that few would have the guts to attempt—and she does most of them sidesaddle.
The first winner of the 2013 Dianas of the Chase Cup point-to-point race held in Leicester, U.K. also holds the World Record for jumping a 6-foot-8-inch puissance wall sidesaddle (you can watch her do it here). This week, Oakes is taking on a new challenge: the inaugural running of the Mrs. Miles B. Valentine Memorial Side Saddle Point-to-Point, part of the 70-year-old Cheshire Races held each year in Unionville, Pennsylvania. The event this weekend will be the first side saddle race held north of the Mason-Dixon Line since the 1930s.
(©Kristie Grabosky)
“I’ve never sat on a horse in America until this morning,” says Oakes, who arrived in Pennsylvania on Tuesday. The County Meath-based rider regularly hunts and point-to-point races both astride and side saddle back home. When asked about her goals for Cheshire, Oakes’s expectations are simple. “Just to experience what the point-to-point and the racing is like here in America,” she says. “It is quite incredible, the difference in countryside, and the jumps are very different. Our hunting country [in Ireland], we would have an awful lot of ditches and hedges, where everything here is timber.”
Oakes’s friend Steph Boyer has provided her with a horse for the day, and a good one at that. Fort Henry, a 15-year-old Irish-bred with a long and storied career as a racehorse both in Ireland and America, where he competed in the Maryland Hunt Cup and the American Grand National steeplechases before being used as a huntsman’s horse by Boyer’s fiancé, Ivan Dowling. Wednesday morning, however, was the first time he had ever been ridden sidesaddle. “Fort Henry is a really lovely, balanced horse, and he’s very comfortable to ride. So when you’re trotting you’re not being bounced out of the saddle. He jumped really, really well with it,” says Oakes.
Is there a steep learning curve when it comes to training a horse to go sidesaddle? As it turns out, not as much as you’d think. “Because I’m quite a balanced rider and I’m so used to it, the horses normally get my confidence straight away, so that really helps,” says Oakes, who’s been climbing into a sidesaddle since she was four years old.
(©Attic Photographic)
Though sidesaddle riding has been historically popular in various circles on both sides of the Pond, many credit the “Downton Abbey effect” for bringing the thrill of a dramatic chase across open countryside—while elegantly decked out in habit, snood, and face veil—to a wider audience.
“I think people appreciate it as an art form—an equestrian art form. And I think it’s making a great comeback. It should be appreciated, because it’s not the easiest thing in the world to ride sidesaddle, and it’s great when people get to see it,” says Oakes, who organizes an annual sidesaddle hunt in County Meath, often attended by more than 50 ladies, including several North American participants. “Many years ago, it was perceived differently… but now everyone has a chance to do it, and that’s the main thing. You have little kids on their ponies flying around and ladies of all ages and experiences.”
The first running of the Mrs. Miles B. Valentine Memorial will take place on Sunday, March 27th with gates opening at 10 a.m. Participants will run the 2-mile course while negotiating a series of 8-10 brush, timber and coop-style fences. Like the U.K.’s Dianas of the Chase Cup before it, the rules are pretty simple. “When the flag falls, everyone takes off and then best person comes home first,” says Oakes.
© Jim Graham
Regardless of how the race plays out this weekend, however, the side saddle rider plans to return to the U.S. for the second and third events in a new point-to-point series, which includes the Mrs. George C. Everhart Memorial Invitational Sidesaddle Race at the Loudoun Hunt in Leesburg, Virginia on April 17th, and theHigh Hope Ladies Side Saddle Race May 22nd in Lexington, Kentucky. In her spare time, Susan Oakes also has her sights set on breaking the world side saddle puissance record yet again: this time in the States, jumping a whopping 7 feet.
“I don’t really ever get nervous, it’s just the general excitement,” says Oakes of her pre-race routine. “I just really enjoy the moment and I try to be present in the moment and make the most of it.”
