Stories from the Saddle: Dan Cherriman
- pporacommittee
- Apr 30
- 9 min read
Dan Cherriman rode his first double at the weekend – at the age of 40 – on Galileo Silver and Hugos New Horse at Woodford, having only had his first winner at 32, and his first ride aged 29.
One of just two serving huntsmen to have ridden a winner, Dan is still actively involved in hunting, as Joint Master-Huntsman for the South Shropshire, and obviously has strong views on the future of point-to-pointing if further restrictions are placed on his career, so Jake Exelby spoke to him about this subject, his journey in the sport, his faith… and pipe smoking!
Talk me through your involvement with horses as a child.
I was born on the family farm at Chiddingfold, on the Surrey-Sussex border. Dad was always keen on field sports like shooting and fishing, while Mum liked ponies, so I grew up doing pony club, eventing and a little bit of hunting.
How did you get into hunt service and what roles have you performed?
Dad had gundogs, so I’ve always loved working dogs. As a teenager, I met the hound puppies, got introduced to the kennels and fell in love with the traditional pageantry involved with hunting. I started volunteering on Saturdays and in the school holidays with the Hampshire and Chiddingfold, Leconfield & Cowdray Hunts and decided that’s what I wanted to do – getting paid to work at the kennels and go hunting was the perfect job!
Aged 18, I went to work for the Quorn and spent seven seasons there as First Whipper-in, effectively assistant to the Huntsman, who’s the senior professional. My main job was to look after the hounds.
While there I met, then married Jessica Dawson. There are few jobs in hunting so, to progress, you have to move, so I went to become Kennel Huntsman at the Glamorgan, then was offered the job of Huntsman at the Pytchley. I was there for ten years.
How did you get into point-to-pointing in the first place?
I’d had no exposure to racing apart from going to the local point-to-point at Parham, but Rowan Cope and Stuart Morris were Joint Masters of the Pytchley and had both been successful point-to-point jockeys. Lots of hunting people I knew had ridden and/or trained – the likes of Johnny Bailey, Sam Davies-Thomas and Tom McClorey.
I’ve always been quite competitive and enjoyed cross-country, so I asked if I could get a horse to ride in the Members. I hooked up with Jo Messenger – whose son Tom was riding professionally at the time and is now assistant to Dan Skelton – as she trained a few pointers at Creaton, where the kennels are based. She’s brilliant at nurturing novices and owner-riders.
Tell me about your early riding career, leading up to your first win with Churchfield Champ.
My first horse was Victor Grumps, who we bought from Dale Peters. He was an old schoolmaster but didn't work out well for me! We got round in our first race, an Open at Bangor-on-Dee, which was a big tick in the box, then finished mid-division at Brafield-on-the-Green, but then the wheels fell off and his jumping went to pot. We fell at the second in our Members, then unseated at the first at Dingley.
I had my first win at Umberleigh, having just turned 32. Churchfield Champ was the first of three horses that I’ve bought, then won on within a week, the other two being Reikers Island, and Hugos New Horse, of course. He was trained by Kayley Woollacott and had won two for Lee Drowne that season, so I thought I could win on him. He was advertised on Facebook, and wasn’t expensive, so I bought him over the phone – the first time I saw him was in the paddock! We won the Mens Open in the fastest time of the day, and it was an absolute dream.
You rode at Cheltenham – on Martin Cash – before you’d had your first winner in a point. That seems quite unusual.
Tom found Martin Cash and it was Jo’s idea to run him at Cheltenham. I was 30 by then and knew I wouldn’t be around forever. While I wasn’t a competent jockey then, I knew how to ride. Cheltenham was just my second ride under rules, and a great experience.
After that, you had horses with Alan Hill. How did that link come about?
I knew Alan from hunting with the Pytchley. In my first season, there was a charity race at Newmarket, and he gave me Royal Etiquette to ride, to support a huntsman. It was – unofficially – my first winner at 30. I went to his to ride out, really enjoyed it, and decided to have a horse with him. My first was Brians Well, and I then bought Stage One, who won three for me.
Tell me about Kashmir Peak and Reikers Island, both of whom you rode at Aintree?
It was my boyhood dream to ride over the National fences, and I realised it could be a possibility with Kashmir Peak, a good pointer, who was qualified for Aintree. The first year I had him, it was cancelled due to Covid then – in the second season – there was no pointing and amateurs couldn’t ride in Hunter Chases until after Cheltenham. You were only allowed to ride at Aintree if you’d ridden under rules that season – I hadn’t, because I was busy hunting, so only had a short window.
I was due to ride Stage One at Warwick, but he was kicked at the start and withdrawn and – by that time – it was too late to make any more entries, so I had to find an outside ride. I got one for Micky Hammond – Excalibur in a Carlisle hurdle. He was carrying ten stone and I claimed 7lbs, but I managed to do the weight. We finished fifth and I could ride at Aintree, where we jumped the first and Mighty Stowaway did the splits in front of me and brought me down!
I thought, ‘I still want to scratch that itch’ and decided to buy a younger horse. Reikers Island was with Richard Newland, fit and ready to run, and we won at Cartmel just after I bought him – my first and only winner under rules.
The next season, we were supposed to be going to Aintree, but I broke my pelvis schooling Kashmir Peak, who ran out through a wing. Huw Edwards rode him and he travelled and jumped lovely to finish seventh, so I was excited about riding him the year after.
In 2023, my boyhood dream finally came true. We finished in the middle order and to get round after four years of planning was brilliant. We went back in 2024, but he hated the soft ground and we pulled up, then last year I rode Percussion for Joss Hanbury, so I was lucky enough to go five years in a row. Hopefully Hugos New Horse can get there next year.
Which has been your favourite horse?
Reikers Island – I won five on him.
What do you think will happen to pointing after a hunting ban?
This is a really important question, and I’m concerned that pointing’s leadership think it won’t be the end of the world if we lose some meetings if hunting goes, because there are too many fixtures and not enough horses.
I think it would have a devastating effect, and that we’d go from having too many fixtures to not enough to sustain the sport. At most point-to-points, the landowner and volunteers doing the less glamorous jobs do it for the hunt, not for racing. You could run it as a charity or club meeting but would have to pay the volunteers so – even if you have the landowner’s permission – you might not be able to afford to run a meeting. If you pull the thread out of hunting, the whole thing begins to unravel.
I can see a scenario where you have a small number of tracks like Chaddesley Corbett, Garthorpe, Kingston Blount and Larkhill, but the once-a-year courses like Guilsborough would disappear. Pointing’s probably the only sport organised by a different one (hunting). It would be like the FA organising rugby!
Are you aware of any other huntsman who do currently ride, or have recently ridden, in point-to-points?
Mick Wills, who was Huntsman with the Grafton, had ridden in points (and at Cheltenham, like Dan) and won a race. Apart from him, I can’t think of any. For a long time, hunt servants were classed as professionals, so couldn’t ride in points, and most Masters don’t want their staff getting injured race-riding. Some Joint Masters, like Henry Bailey with the Wynnstay, ride in points.
The Shropshire pointing scene seems strongly associated with hunting, with the likes of Guy and Iola Sankey and Henry Bailey all keen hunters and active jockeys. Why do you think that is?
It seems to have clung on to its hunting connections better than other areas, with the likes of Chris Stockton, the Greenalls and Richard Burton.
Which other jockeys do you admire?
Tommie O’Brien is steely, wily and kind enough to give me advice. I think highly of him. And Johnny Bailey was at the top of his game when I started. He was local to me, was helpful in the weighing room, and would phone me and lift my spirits when things weren’t going so well.
What's your favourite course?
Godstone. At my level, you pick unfashionable courses to ride. I’ve had a couple of winners there, it’s a fun day with a good crowd and the hospitality’s fabulous – they really look after owners. I think that, because the South East has low horse numbers, they try harder to attract people from outside the area.
What are your ambitions in pointing and racing? You’re now 40, so how long do you think you’ll keep riding?
I’ve got three children – Jack’s 10, Ted’s 7 and Sidney’s 3 – and Jack is already pony racing. Will I keep going long enough to ride against him? I don’t feel old – when I started, I felt like an up-and-coming jockey – so if I’m physically able and the desire’s there, I’ll keep going.
When we moved to Shropshire, the plan was to ride at Aintree then retire but, because I came down at the first, I wanted to go back. And watching it on TV this year renewed my hunger to go back. It’s a special place. Cheltenham doesn’t do it for me the same way.
You also train your own Punch Perfect. What made you decide to do that?
Training’s a new string to my bow. I bought him ‘oven ready’ from Josh Newman. We’ve got stables at home and training him myself saves a bit of money – it’s fun to have a go with an inexpensive horse, although it’s hard during the winter when I do so much hunting and daylight hours are shorter. He’s jointly owned with Ruth Elaine de Quincey, who owns Galileo Silver, and we’re going to Godstone on Saturday.
What would you do if you were in charge of the sport?
I’m not sure I’m qualified to answer! But I’d bring back the Veterans category for Novice Riders races. It’s the first year I’m a Veteran, and they’ve scrapped it.
What would you be doing if you weren’t involved with horses?
It’s a light-hearted question, but an area of big concern. Pointing and hunting are two of my passions, and one’s coming to an end, with the other under threat. When I was younger, I wanted to join the Army and I enjoy writing – I write for Horse & Hound – and public speaking. I guess anything I do would involve horses and/or dogs.
I know that you’re a regular churchgoer, often before racing on Sundays. How does that work alongside your riding?
I’m a Christian with an active faith and it’s human nature to think we’re the centre of our lives, but putting God first is important to me – after all, He’s given me the physical ability to ride horses.
Yes, I make sacrifices and can’t ride every Sunday, but race-riding’s a hobby and I often want to prioritise church and family, even if it means missing racing.
As far as I’m aware, you’re the only jockey to smoke a pipe. When did that start and why?
Aged 16, I went to an agricultural show and saw an old-fashioned tobacconists stand and bought a bargain basement pipe with tobacco for a fiver. I’ve smoked, occasionally and for a bit of fun, ever since. I give it up from time to time – during Lent for example – to make me think I’m not addicted (!) but really enjoy it after a day’s hunting or racing.
Dan Cherriman is sponsored by his family business, Ryestead Estates.
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