Camaraderie, poise and a healthy dose of Dutch courage were the order of the day when 16 women with nerves of steel took on the Leicestershire countryside for the inaugural Bernard Weatherill Diana of the Chase Cup—the first recorded sidesaddle race to be held since 1921. “Originally I was interested in point-to-pointing but I realized you couldn’t ride them sidesaddle so you might as well organize your own race,” says jewelry designer Philippa Holland, who hatched the plan for the steeplechase after when former Formula One driver Brian Henton invited her to host the event on his farm. Although this equestrian art nearly died out after the Second World War, it has recently undergone a revival with social media serving as a platform to galvanize and unite enthusiasts. Apart from Holland herself, competitors included seasoned riders such as Martha Sitwell, the face of Royal Ascot, and eventer Fiona Davidson. “It’s the combination of glamour and bravery,” says Holland. “You don’t want to be trotting around being judged for your turnout—you want to be galloping across country brave as anything and looking elegant at the same time.” The race, drama and romance that photographer Linda Brownlee captured was ultimately won by Navan-based entrepreneur Susan Oakes, who also set the record for side saddle high jump in July last year.