Chester Boodles May Festival 2026: Full Schedule, Must-Watch Races & Early Predictions

Trials Day at Boodles May Festival

Opening at 1:30 on Wednesday with the CAA Stellar Lily Agnes EBF Conditions Stakes, Trials Day is the one for serious racing fans. 

There are seven races in total, with highlights including both the Weatherbys Cheshire Oaks (2:35) and the Boodles Chester Vase Stakes (3:05) scheduled. The full schedule is listed below: 

• 1:30: CAA Stellar Lily Agnes EBF Conditions Stakes 

• 2:05: Join Ladbrokes Bet 5 Get 30 Earl Grosvenor Handicap 

• 2:35: Weatherbys Cheshire Oaks 

• 3:05: Boodles Chester Vase Stakes 

• 3:40: American Holidays Handicap 

• 4:10: TMT Group Maiden Stakes 

• 4:45: Roodee Handicap Cl3 

The Weatherbys Cheshire Oaks is a trial for the Epsom Oaks for fillies and features the likes of I’m The One, Amelia Earhart and Sugar Island. The Boodles Chester Vase is one of two trials run at the meeting for the Epsom Derby, featuring Benvenuto Cellini, Water To Wine, and Del Maro.

Ladies Day at Boodles May Festival

Ladies Day is all about donning your favourite dress and supporting your favourite runners. It’s as much a social gathering as it is a sporting event – but that doesn’t mean the racing suffers, far from it. 

There are seven races to catch – the highlights of which are the Boodles Raindance Dee Stakes (2:35) and the Ladbrokes Ormonde Stakes (3:05). The full schedule is listed below: 

• 1:30: CAA Stellar Handicap 

• 2:05: British Stallion Studs EBF Maiden Stakes 

• 2:35: Boodles Raindance Dee Stakes 

• 3:05: Ladbrokes Ormonde Stakes

• 3:40: Xenon Workplace Handicap 

• 4:10: Halliwell Jones Handicap 

• 4:45: Chester Handicap 

Keep your eyes peeled for Al Qareem in the Ladbrokes Ormonde Stakes; he’s no stranger to a win around these parts and appears to be in great form. 

Ladbrokes Chester Cup Day at Boodles May Festival

We’re treated to an extra race for the final day of the Boodles May Festival, with eight races instead of the standard seven expected to run. 

Highlights include the Deepbridge Huxley Stakes (2:35) and, of course, the Ladbrokes Chester Cup (3:05). The full schedule is listed below: 

• 1:30: CAA Stellar Great Cheshire Handicap

• 2:05: Boodles Darley EBF Maiden Stakes 

• 2:35: Deepbridge Huxley Stakes 

• 3:05: Ladbrokes Chester Cup

• 3:40: Tom Jones Live At Chester Racecourse Handicap 

• 4:10: Ladbrokes Get A Free Race Bet Today Chester Plate Handicap 

• 4:45: Irish Thoroughbred Marketing Handicap 

• 5:20:Chester Roman Day On 30th May Apprentice Handicap

Harry Davies has won the Ladbrokes Chester Cup – the Festival’s big one, for the last two years running. First with Zoffee in 2024, then again with East India Dock in 2025. He’s not yet booked a ride for the 2026 running – but with such an impressive track record, it’s hard to look past anyone else (if he’s confirmed to run, that is). 

What to Watch at Boodles May Festival

If you’re searching for a highlight reel of the Boodles May Festival, it’s the mid-afternoon races (listed in bold above) that promise the most action. 

The Ladbrokes Chester Cup should, of course, be at the top of everyone’s list. Trained by Sir Mark Prescott Bt, Blindedbythelights is one of my top picks, but Harry Davies is going to be the one to beat – we’re just waiting for confirmation of his booking.

For more horse racing predictions and tips, read Adam Mace's weekly recommendations.