May Festival

Chester Racecourse, popularly known as 'The Roodee', has the distinction of being the oldest racecourse in operation, according to Guinness World Records, having staged its first recorded race on January 10, 1539. The May Festival, of which luxury jeweller Boodles has been the official, title sponser since 2013, is the most presitigious meeting of the year at Cheshire course. In 2025, the May Festival is schedule for Wednesday, May 7 until Friday, May 9 and, as is customary, consists of Trials Day, Ladies Day and Chester Cup Day. Free Bets UK and other sites will be doubt be helping you make the most of your money.

The Group 3 Chester Vase, run over a mile and half and restricted to three-year-olds, is a recognised trial for the Derby at Epsom on the first Saturday in June and, as such is the feature of a seven-race card on Trials Day. The race was won, by 12 lengths, by the subsequently ill-fated Shergar, en route to a still-record 10-length win on Epsom Downs in 1981, while the most recent participant to win the Derby was Wings Of Eagles, who finished second to stable companion Venice Beach in 2017 before defying odds of 40/1 in the Epsom Classic.

Ladies Day, as the name suggests, is a visual spectactle off the course, but on it the Group 3 Ormonde Stakes, run over an extended mile and five furlongs and open to horses aged four years and upwards, is the undoubted highlight. Notable past winners include Harbinger who, like Shergar, was trained by Sir Michael Stoute and remains, jointly, the ninth highest-rated Flat horse in the history of Timeform.

Again, as the name suggests, Chester Cup Day belongs to the Chester Cup, a 'Heritage Handicap', established, as the Tradesmen's Cup, in 1824, run over an extended two and a quarter miles and open to horses aged four years and upwards. Worth £170,000 in guaranteed prize money, the Chester Cup has a safety limit of 17, but is inevitably over-subscribed. So much so, in fact, that horses balloted out of the main event have an opportunity to contest a consolation event, the Chester Plate Handicap Stakes, run over the same distance as the last race on the card.