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.