May Racing Weekend

Racing on the Roodee since 1539; older than almost everything, and still running.

The first recorded horse race at the Roodee in Chester took place in 1539, making it the oldest racecourse still in use in England. The course sits on a small, flat meadow beside the River Dee, enclosed by the ancient city walls. Early races were rough affairs, run for a civic prize and watched by the Mayor and Corporation from the city walls above.

A trial for three-year-olds with Classic dreams, the Dee Stakes has been separating contenders from pretenders since 1813.

The Dee Stakes, named after the river that curves alongside the course, was first run in 1813. It quickly became a key trial for three-year-old colts with Classic ambitions. The race remains a Listed contest and a regular feature of the May meeting, offering trainers a searching test over a mile and a quarter on Chester's demanding bends.

Two centuries on, the Chester Cup still rewards craft over raw pace on the Roodee's relentless bends.

The Chester Cup was inaugurated in 1824 as a handicap over two miles and two furlongs, and it remains the centrepiece of the May meeting. Run over nearly two full circuits of the tiny Roodee, it demands stamina, tactical nous and the ability to handle relentless turns. The race has produced some of the most dramatic finishes in flat racing, with the tight track ensuring that positioning and jockeyship matter as much as raw speed.

Since 1907, Chester's twisting mile and a half has been separating genuine Derby contenders from hopeful pretenders.

First run in 1907, the Chester Vase was established as a trial for the Epsom Derby. Run over a mile and a half, it gives three-year-olds a stern examination on a turning track before the wider expanses of Epsom. Several Chester Vase winners have gone on to Derby glory, cementing the race's reputation as one of the most reliable Classic pointers in the calendar.

Named after an unbeaten champion, the Ormonde Stakes has given older horses a stage worthy of their talent since 1936.

Named after the legendary unbeaten racehorse Ormonde, trained by John Porter and owned by the 1st Duke of Westminster, the Ormonde Stakes was first run in 1936. The Group 3 contest over a mile and five furlongs gives older horses a chance to shine during the May meeting, adding further depth to a fixture already rich in quality.

Corporate racing days outside Royal Ascot rarely rivalled Chester's May meeting once the grandstands went up.

Through the 1990s, Chester Race Company invested heavily in upgrading facilities, building new grandstands and improving hospitality areas while preserving the intimate character of the Roodee. The May meeting benefited enormously, with corporate hospitality becoming a major draw alongside the racing. The combination of a compact, atmospheric venue and high-quality fixtures made it one of the most sought-after corporate racing days outside of Royal Ascot.

Three days, three distinct personalities. the Roodee rewards those who stay to the end.

Chester's May meeting grew into a full three-day festival, typically running from Wednesday to Friday in early May. Each day carries its own character: the Chester Vase and Dee Stakes anchor the middle day, while the Chester Cup provides the climax on the final afternoon. The expansion reflected growing demand from racegoers and corporate guests alike, drawn by the quality of racing and the unique atmosphere of the Roodee.

Prize funds north of £300,000 across two races alone; the Roodee has never paid out so well.

The May Racing Weekend remains one of the most anticipated fixtures in the British flat racing calendar. The Chester Cup carries a prize fund exceeding £170,000, the Chester Vase is a Group 3 contest worth £140,000, and the Ormonde Stakes continues to attract high-class older horses. With Boodles and Ladbrokes among the sponsors, and Sky Sports Racing broadcasting every race, the meeting has never been more visible. Yet the Roodee's charm endures: the city walls still offer a free vantage point, and the tight turns still catch out the unwary.