Chester Racecourse: The Oldest and Roundest in the Land

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Chester Racecourse Bend

One of the big advantages UK horse racing has over its international counterparts is the varied selection of racecourses. While other nations tend to follow a standard layout – usually completely flat and oval – British racecourses come in all manner of shapes and sizes. Figure-of-eight tracks, rollercoaster-like undulations, and twists and turns all feature alongside more conventional layouts. Given that diversity – no two UK tracks are exactly alike – it takes a special type of racecourse to earn the label “unique”.

Nevertheless, there are several singular tracks contained on the list of 59 British racecourses – none more so than the beautiful North West venue of Chester. Located within a stone’s throw of the city centre, Chester Racecourse scores top marks for location, heritage, the quality of the racing, and sheer “roundness”.

Chester Racecourse: The Guinness World Record Holder

The land on which Chester Racecourse resides was reportedly used as a Roman harbour during the grim-sounding Dark Ages. Later repurposed as a sporting destination, the open fields hosted the notorious Gottesday football match, which by all accounts resembled little more than a mass brawl. Presumably tired of dealing with the aftermath of the Gottesday game, Chester’s mayor, one Henry Gee, banned the annual bloodbath in 1533. He then gave the go-ahead for a more civilised activity when granting permission for the racecourse to be built.

With Henry VIII atop the throne and onto wife number four, Chester Racecourse was born in 1539. So too was the term “Gee-Gees” as a nod to the mayor who made the whole operation possible. Now closing in on its 500-year anniversary, Chester Racecourse is the oldest racecourse still in operation on the planet – as confirmed in the Guinness Book of World Records.

What’s in a Name? The Tale of a Nunnery or a Murderous Statue?

When tuning into Chester races on TV, you will almost certainly hear the track referred to as the Roodee. The exact origins of this term have been lost to the sands of time, but theories abound. Most agree the term Roodee relates to a cross in the centre of the course, resting on a raised mound – the rough translation of Roodee being “Island of the Cross”. However, the stories behind the cross vary widely.

The most mundane explanation states that the cross represented the boundary of an ancient Benedictine Nunnery in the area. More interesting is the assertion that the cross marks the resting place of a murderous statue of the Virgin Mary. Hoping for rain, Lady Trawst, wife of the Governor of Hawarden, headed to church to pray. Legends suggests those prayers were emphatically answered by a thunderstorm and a dislodged tumbling statue, which ended the good lady’s life. Not ones to let a statue get away with such an act, the Chester locals arranged for the statue to be tried by jury. Offering no protest, the statue was found guilty, hanged for its crimes, and buried on the land that is now Chester Racecourse. A fine story, true or not!

A Compelling Mix of the Old and the New

Chester Roman Walls and Cathedral

A visit to Chester Racecourse presents a unique blend of the old and the new. On one side of the course, the grandstands offer all the facilities you would expect of a modern race-day experience. On the other side, the track nestles against the ancient city walls, often populated by locals taking the opportunity to take in the action for free.

In recent years, Chester has invested heavily in improving the spectator experience, adding high-spec hospitality suites, panoramic viewing areas, and digital facilities that retain the charm of the old Roodee while meeting the expectations of a 21st-century crowd.

Despite the modern gloss, Chester remains tied to its rich and distinct heritage and it’s all the better for it. Newer venues can never match the entrenched heritage, while few old courses have been brought into the modern age so effectively. Throw in a vibrant atmosphere regularly bolstered by a significant Liverpudlian element, and you have one of the most appealing race-day experiences in all of British racing.

A Singularly Circular Experience

Besides the rich history, unusual nickname, and invariably excellent atmosphere, Chester is best known for the layout of the track. At a little over a mile in circumference, Chester is one of the smallest and tightest tracks in all of British and Irish racing. Whatever the distance, runners turn left-handed for the bulk of their journey, with the only brief respite arriving in the home straight of just over a furlong.

This near constant left-handed turning brings two factors into play when selecting your Chester bets. Firstly, those drawn low hold a distinct advantage – if you are going to be racing around a bend, it’s far better to start towards the inside of that bend. Secondly, long striding galloping types tend to struggle at a track which favours nippier sorts who like to race handily.

Festival Time: The Marvellous Month of May

Such a historic track deserves a prominent position in the racing calendar, and Chester duly gets it. Around 15 fixtures take place on the Roodee each year, but the clear highlight arrives in the shape of the three-day May Festival.

Taking place over a Wednesday, Thursday, and Friday in early May (when else?), this three-day feast of action is one of the most well-attended midweek meetings of the year. Sandwiched between the Guineas meeting at Newmarket and Epsom Derby Festival, this early summertime highlight is regularly bathed in sunshine. Featuring five races rated at Listed level or above, the track’s most famous handicap – the Chester Cup – and a sell-out Ladies’ Day, this outstanding fixture is the meeting that thrusts Chester Racecourse onto centre stage.

Classic Winners on Show

Away from the ancient and unusual heritage, distinctive atmosphere, and disc-like layout, a visit to Chester Racecourse may also afford the sight of a bona fide racing superstar in the flesh.

Given the demands the track places upon balance, many trainers view Chester as an ideal stepping stone towards the Epsom Classics. The Chester Vase, Dee Stakes, and Cheshire Oaks are all recognised as key Classic trials, and regularly attract runners from the leading British and Irish yards. All three races have a history of producing the winner of the Derby and Oaks.

Kris Kin won the Dee Stakes before his Derby success in 2003, while 2017 runner-up Wings Of Eagles went on to cause a 40/1 shock at Epsom. More recently, Minnie Hauk and Lambourn landed the 2025 editions of the Cheshire Oaks and Chester Vase before going on to Oaks and Derby glory in June.

Almost 500 years of history, a Guinness World Record, Classic winners aplenty, and a buried statue of the Virgin Mary (allegedly), this gem of a track on the banks of the River Dee is one of the true icons of the British racing scene. A must-visit destination for all UK racing fans and indeed racing lovers fullstop.