A History of Chester Races

Chester, also known as the Roodee, is officially recognised as the world’s oldest racecourse, and races at Chester have played a significant role in horse racing’s history.

First established in 1539, Chester Racecourse rests on the banks of the River Dee in Chester, England. It is nicknamed the “Roodee” because the original site was submerged underwater for several centuries until an accumulation of silt produced an island in the middle of the River Dee.

A stone cross was built in the centre of the island during the middle ages and dubbed the “Rood Eye”, a combination of ancient Norse and Saxon languages for “Island of the Cross.”

Small mounds still occupy the centre of the modern racecourse, one of which is marked with a stone cross.

The beloved venue has attracted some noteworthy figures over the years, including legendary showman Buffalo Bill, who attended the Roodee in 1903.

From the Royal Family to celebrities and TV personalities, Chester is no stranger to the rich and famous, with Sir Cliff Richard spotted in 2019, Manchester United’s Cristiano Ronaldo in 2017, and Queen Elizabeth II sighted in 1966.

There’s no denying that Chester is steeped in history. Discover the heritage of Chester races and the role the UK’s smallest racecourse played in the evolution of British horse racing.

480 Years of Racing at Chester

Although Chester was established in 1539, racing at the Roodee can be traced back to 1512.

The site has been used for sports outside of horse racing too, as Chester hosted the infamous Goteddsday football match in 1533.

While the Boodles May Festival is the most popular meeting at Chester, there have been several thrilling races at the Roodee and three momentous occasions in modern era horse racing history.

The first recorded prize presented to a horse racing victor was at a Chester fair in 1512. The award was a hand-painted wooden bowl – a slight change from the prizes champions receive today!

The second notable event at Chester revolves around Henry Gee, who became the city mayor in 1539. During his reign, Mr Gee introduced an annual horseracing meeting at the Roodee and made it so race winners would receive silver bells instead of a hand-painted wooden bowl.

Henry Gee became synonymous with horse racing due to his involvement in the sport, which saw racehorses nicknamed “gee-gees” as a result! The popularity of horse racing in Chester made it economically viable to build the first grandstand at the racecourse, constructed in 1817.

Racing fixtures at Chester are highly sought after by racing enthusiasts, with the unique 1 mile, 1 furlong course comprising of tight turns providing thrilling sights for spectators.

Chester May Festival 2024 - Chester Racecourse - Silks Restaurant Hospitality - Racecourse view

What are the Most Popular Chester Races?

During the early years after its establishment, Chester hosted two meetings, one of which took place on Shrove Tuesday and the other on St. George’s Day.

Fast forward almost 500 years, and there are now 15 fixtures annually, including the highly renowned Chester May Festival, which attracts approximately 50,000 racegoers each year.

The May Festival kick starts the racing season at Chester, with contenders going head-to-head in seven high calibre races across three days. The most iconic Chester races are as follows:

Cheshire Oaks Cup History

The Cheshire Oaks Cup gets underway on the first day of the May Festival and boasts a prize pot of £87,500. First established in 1950, it’s run over a distance of 1m 3f 75y and is open to three-year-old horses.

Notable winners of Cheshire Oaks Cup include:

  • Enable in 2017 ridden by Frankie Dettori
  • Bolas in 1994 ridden by Pat Eddery
  • Shoot A Line in 1980 ridden by Willie Carson

The Cheshire Oaks Cup often serves as preparation for the Epsom Oaks, with the only horse to have won both races being Khalid Abdullah-owned Enable.

Chester Vase History

The Chester Vase is another highlight race, which features on the Wednesday of Chester May Festival, dubbed City Day.

It’s run over a distance of 1m 4f 66y and, with a prize pot of £110,000, attracts some of the finest sprinters in Britain, making for an incredible atmosphere in the stands.

Some memorable Chester Vase winners include:

  • Treasure Beach in 2011 ridden by Ryan Moore
  • Old Vic in 1989 ridden by Steve Cauthen
  • Shergar in 1981 ridden by Walter Swinburn

Legendary trainer Aidan O’Brien has dominated the Chester Vase in recent years, boasting a record of 9 wins in the race, which made its festival debut in 1907.

Ormonde Stakes History

On day two of the Chester May Festival, also known as Ladies Day, the Ormonde Stakes takes centre stage.

The Group 3 flat race – first established in 1936 – is run over a distance of 1m 5f 89y and has a prize fund of £100,000 in 2022. It was initially open to racehorses aged three years and older but was confined to three-year-olds in 1955, before being restricted to older horses three years later.

Notable winners of the Ormonde Stakes include:

  • Rakaposhi King in 1987 ridden by Steve Cauthen
  • Teenoso in 1984 ridden by Pat Eddery
  • Ninisniki in 1980 ridden by Willie Carson

Aidan O’Brien-trained Japan is the most recent winner of the Ormonde Stakes, blitzing the field to win by a clear margin.

Dee Stakes History

The Dee Stakes is also held on the Thursday of the Chester May Festival. The Listed race is one of the older fixtures still in operation at Chester, having first been established in 1813 and is run over a distance of 1m 2f 75y.

The name of the race stems from the River Dee, which runs alongside Chester Racecourse. Notable winners of the Dee Stakes include:

  • Magician in 2013 ridden by Ryan Moore
  • Sohaib in 2002 ridden by Richard Hills
  • Sir Harry Lewis in 1987 ridden by Cash Asmussen

Like the Cheshire Oaks Cup, the Dee Stakes is also considered a significant trial for the Epsom Derby and attracts a lot of attention from punters and bookmakers.

Huxley Stakes History

First established in 1999, the Huxley Stakes takes place on the Friday of Chester May Festival and is run over a distance of 1m 2f 75y.

It’s one of the most expensive races at the Boodles May Festival, boasting a prize pot of £137,500 in 2022. The race, which officials upgraded to Group 2 status in 2018, is named after Huxley village located to the east of Chester.

Memorable winners of the Huxley Stakes include:

  • Notable Mission in 2014 ridden by James Doyle
  • Debussy in 2010 ridden by William Buick
  • Chester House in 1999 ridden by Kieren Fallon

Ryan Moore is the leading jockey of the Huxley Stakes, having won the race six times in the last 20 renewals.

Chester Cup History

The Chester Cup, which was called the Tradesman’s Plate until 1892, is the feature race of the Boodles May Festival and takes place on the final day of the meeting.

First established in 1824 and run over a distance of 2m 2f 147y, it’s the Chester May Festival’s longest race. It’s also one of the major handicaps in the British horse racing calendar and regularly attracts high profile sprinters.

Notable winners of The Chester Cup include:

  • Trip to Paris in 2015 ridden by Graham Lee
  • Overturn in 2011 ridden by Eddie Ahern
  • Grey Salute in 1989 ridden by Pat Eddery

Nine horses have won the race more than twice, including Rainbow High, Top Cees, Anak Pekan and the Champion Hurdler Sea Pigeon.

When is the Chester May Festival 2024?

In 2024, the Chester Boodles May Festival is scheduled for Wednesday 8th May 2024 – Friday 10th May 2024

When is Chester May Festival Ladies Day?

Ladies Day at Chester always takes place on Thursday, with Chester City Day on Wednesday and Chester Cup Day on Friday. In 2024, Boodles May Festival Ladies Day 2024 takes place on  Thursday 9th May 2024

Although Chester does not impose a strict dress code, smart attire and glamour are encouraged! Gentlemen are advised to wear either a well-tailored suit or jacket and smart trousers, while ladies are asked to adorn “smart dress”.

Chester May Festival Hospitality

If you fancy attending one of the most historic meetings within the horse racing calendar, why not experience it in luxury?

Our Chester May Festival hospitality packages are guaranteed to make your day at the races more memorable. Our course-facing facility, Silks Trackside Pavilion, is a firm favourite among our clients, offering guests the opportunity to indulge in a four-course fine dining experience, complimentary bar and afternoon tea, among various other VIP luxuries.

Have an enquiry about Chester hospitality?

Chester May Festival

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