September 23, 2023

Celebrating a half-millennium of racing at Britain’s historic Chester

The ancient city walls adjoin Chester, the world's oldest active racecourse (Steve Davies/

As British racing authorities map out plans to reschedule the classics amid the COVID-19 pandemic, other fixtures aren’t so fortunate. This week’s festival at Chester is the latest casualty. Although its classic trials – the Chester Vase (G3), Dee S., and Cheshire Oaks – are lost, along with the Ormonde (G3), Huxley (G3), and Chester Cup for the older set, we’ll pay homage by celebrating the track’s rich history.

Chester is described as the world’s oldest active racecourse, according to a precise definition. The Curragh has far greater antiquity if you count the Celts’ equine pursuits from Iron Age chariots through finer riding horses. But in the context of continuous race meetings backed up by written records, Chester takes the honors for going strong for about 500 years.

The city itself, south of Liverpool and near the Welsh border, is much older. Chester still sports its 2,000-year-old Roman walls, the best preserved circuit from that era in Britain, abutting the track. What is now the racecourse was then a harbor on the River Dee.

After the legions abandoned Britain in 407 A.D., as the Western Roman Empire began to crumble, natural processes took over. Silt deposited by the Dee formed an island. A Cross was erected, giving rise to the name Cross Island – or in the hybrid Saxon-Norse term, the “Roodee” (variously styled “Roodeye”), still the beloved nickname for the racecourse.

The industrious medieval inhabitants did engineering work in the area, building a weir to regulate the Dee. As a result, the river yielded substantially more silt. The island spread out, evolving into a meadow that made for a fine racing surface.

The year 1512 marks the first record of a prize for a horse race in Great Britain. The contest was staged at the Chester fair, the winning owner awarded a painted wood bowl.

The first annual race meeting arose in 1539, thanks to the reform agenda of Mayor Henry Gee. Gee’s initiative is reportedly the origin of the slang “gee-gees” for racehorses.

Horse racing was an upgrade from Chester’s previous activity on Shrove Tuesday, a brawling football match the day before Ash Wednesday ushered in the penitential season of Lent. The horses raced for the prize of a silver bell furnished by the Saddlers’ Company. According to an authority in the latter part of the 16th century, the winning horse got to wear the two-ounce silver bell:

“the which said silver bell was ordayned to be the rewarde for that horse, which with speedy runninge, then should rune before all others.”

To put Chester’s origins as a racetrack in context, Henry VIII was king, and only halfway through his six wives. (Third wife Jane Seymour had died in childbirth in 1537, and his brief marriage with Anne of Cleves came in 1540.) Martin Luther was still alive, the Protestant Reformation barely two decades old, Charles V was still Holy Roman Emperor, Hernando de Soto hadn’t found the Mississippi River, Ivan the Terrible was not yet Tsar, and the Gregorian calendar was still about four decades in the future.

And Chester was already racing.

Newmarket rose to prominence the following century, thanks to racing enthusiast Charles II, whose mount “Old Rowley” gave his name to the “Rowley Mile.” Not until 1711 did Queen Anne bring Ascot to life. The Derby at Epsom didn’t come along until 1780, and its very founding testifies to Chester’s venerable status. The classic was set for June so as not to clash with Chester in May.

Only war has broken the continuity of the Roodee. The English Civil War of the mid-17th century took its toll on the sport in general, with Cromwell’s Puritan regime banning racing as a vice. The world wars of the 20th century also interrupted the usual pastimes.

Befitting its distinguished history, Chester has hosted some of the sport’s greats. The marathon Chester Cup, inaugurated in 1824, has been won by the outstanding Alice Hawthorn (1842), by some accounts the winner of as many 52 races and a tap-root mare of lasting influence, and *Leamington (1857 and 1859), the future leading sire in North America responsible for Iroquois, Longfellow, Parole, and Aristides. The legendary gelding Brown Jack captured the Chester Cup in 1934, the same season he won the Queen Alexandra at Royal Ascot for an incredible sixth straight year. The great hurdler Sea Pigeon was a two-time Chester Cup hero (1977-78), and in 2015, Trip to Paris progressed from this 2-mile, 2 1/2-furlong heritage handicap to take Royal Ascot’s Gold Cup (G1).

The Chester Vase honor roll includes several Derby winners, from the memorable Hyperion (1933) and Shergar (1981) to *Papyrus (1923), Windsor Lad (1934), Henbit (1980), and most recently Ruler of the World (2013). Bayardo, the 1909 Chester Vase hero, by rights should have been on that list if not hampered at Epsom when Sir Martin (Sir Barton’s half-brother) fell.

As a trial shorter than the about 12 1/2-furlong Chester Vase, the 10 1/2-furlong Dee has accordingly produced fewer Derby winners. Sainfoin (1890) turned the double when the Dee was staged at the Derby distance, but only Parthia (1959), Oath (1999), and Kris Kin (2003) have managed to do so in its modern incarnation. Yet the Dee has significance beyond Epsom, with such winners as leading sire Touchstone (1834), a building block of the breed, and in our own day, 2013 Breeders’ Cup Turf (G1) star Magician.

The classic trial for fillies, the Cheshire Oaks, launched Enable on an unsuspecting world in 2017. One year later, Magic Wand made a successful stakes debut on the way to her lucrative globetrotting. Other victorious alumnae who mixed it up with males are Cantelo, heroine of the 1959 St Leger; *Lupe II, queen of the 1970 Oaks at Epsom as well as the 1971 Coronation Cup; and Shoot a Line, the 1980 Irish Oaks winner and a hard-trying second to Ardross in the 1981 Gold Cup. You might remember seeing Shoot a Line’s name in the pedigree of her grandson, 1995 Triple Crown near-misser Thunder Gulch.

Unbeaten English Triple Crown legend Ormonde (1886), bred and raised at nearby Eaton Hall, is memorialized by the race in his honor. Ironically, the first winner of the 13 1/2-furlong Ormonde, Quashed (1936), later edged U.S. Triple Crown winner Omaha in the Gold Cup. Alycidon prevailed in 1949, the year he swept the “Stayers’ Triple Crown” comprising the Gold Cup, Goodwood, and Doncaster Cups. *Tulyar (1952) won the Ormonde as a 3-year-old, during his championship campaign highlighted by the Derby, Eclipse, King George VI & Queen Elizabeth, and St Leger. Fellow Derby winners Blakeney (1970) and Teenoso (1984) prevailed the year after Epsom. In recent years, the Ormonde was a stage for Harbinger (2010) and St Nicholas Abbey (2011) on his way to Breeders’ Cup Turf glory.

A fairly new fixture, the 10 1/2-furlong Huxley, was established in 1999 but harkens back to an older association. Its trophy, the Tradesman’s Cup, alludes to a former name for the Chester Cup. Frankel’s brother, Noble Mission (2014), is the best British performer to take the Huxley. From a North American racing perspective, though, the Huxley is a pointer to success on our side of the pond with such winners as Chester House (1999), Debussy (2010), and Cannock Chase (2016). So did Deauville (2017), only the year after he’d plundered the Belmont Derby (G1).

Indeed, Chester’s left-turning mile circuit puts a premium on the handiness, agility, and mental focus required around similar contours stateside. That’s why racing fans and history aficionados alike can appreciate the Roodee.

To get insights into the unique vibe of Chester, watch this video from the track’s website:

Chester Racecourse – 480 Years in the Making – Our Story Continues from Chester Racecourse on Vimeo.


The Chester Racecourse website is a great resource for the early history. Stakes honor rolls are readily accessible online, including at, and is a treasure trove for historical Thoroughbred biographies. For more color than included here, see Alan Shuback’s Global Racing, pp. 11-16, and Roger Longrigg’s History of Horse Racing, especially pp. 29-30 (source of the silver bell quote), 39-40, 49, and 141.