How Caitlin Oldham Seized the Opportunity of a Lifetime

British eventer Caitlin Oldham is starting her own training business – and she’s basing out of William Fox-Pitt’s yard in the United Kingdom. After working for riders such as Harry Meade, Caitlin is ready to spread her wings while also continuing her own education. We caught up with Caitlin as she gets ready for the next step in her career. You can learn more about her background and business at

Photo by Jay Photos.

EN: What made you decide to pursue eventing as a professional? What gave you “the eventing bug”?

CO: I have always been an extremely competitive person, in all areas of life and sport. I used to play at county level in 4 or 5 sports ranging from hockey to handball to fencing. As I moved through school, however, I had to narrow down my sport intake to make time for studies and horse riding always made the shortlist. When I went to Millfield to study for my A-levels, I had to pick one and again the horses prevailed. I chose to bring my mare Lilly with me and specialise in Eventing. Despite my love for all kinds of sport, I was never a specialist in any so eventing seemed more my speed: not getting too hung up on one thing and being able to keep it varied and interesting day to day.

EN: How did you end up at Harry’s, and what were some of the primary takeaways you learned there in terms of your riding and horse management?

CO: I knew when I left school, I wanted to carry on eventing but wasn’t ready to go on my own and it still seemed sensible to have a Plan B, so I went to the University of Surrey to study Sports Science. I had an incredible first year but juggling trying to develop my riding and continue my studies meant I wasn’t doing as well as I wanted in either. I chose to drop out after my first year and become a working pupil at a professional yard where I could get stuck in. I could go back to uni but I couldn’t go back to being young!

I sent my application to many riders, but Harry was the one I chose. He is one of the loveliest people I have ever had the pleasure of working for and I knew as soon as I met him that we would get on. His work ethic and methods have been inspiring to learn from and being a member of his team has put me in such great stead for the future!

I was able to take notes on all his methods of training and favourite exercises which I will certainly be implementing in my future programs. But my biggest take away is his aptitude for kindness and giving. He is always on the end of the phone for anyone who needs help in any sphere; his manner and honesty are delightful and his approach to care and thoughtfulness for others is unmatched. I have learnt about the kind of atmosphere all people involved with the rider deserve, from owners to sponsors to staff and beyond. I can only strive to bring even half the amount of joy and pleasure for people who choose to be involved with me as Harry does for members of his team. It is truly incredible.

EN: What has been the biggest challenge as a young professional?

The biggest challenge of being a young rider has been being part of such a big pool of riders. I wasn’t born into a horsey family and haven’t moved up through the age rankings so trying to get the right support and becoming a professional hasn’t been straightforward. Nonetheless, I know this will only make me work harder and be more grateful when I achieve my dreams. I hope that through networking with members of our incredible sport as I grow I will find the right people to continue to grow with. There is so much joy and fun to be had for anyone involved with riders and I would love to bring handfuls of it to the plate.

EN: Can you give some detail on how yo got to William’s and what your impressions of working with that team have been?

CO: The opportunity to base myself with William Fox-Pitt has already been monumental and I still don’t believe quite it’s happening. Harry kindly helped me get connected with William. as I knew that after my time with Harry I wanted to move towards having my own setup and a bigger string of horses. By being at William’s I am able to have his and his team’s support and guidance whilst finding my own feet and getting a hold of the ropes. He, like Harry, has a wonderful yard full of good people who are passionate and kind. I am very grateful to have such an incredible opportunity.

EN: How has your riding evolved as a result of your continuing education?

CO: Under the watchful eyes of Harry, Yogi Breisner, William and Tim Rogers, my riding has come on immensely. My dressage scores are dropping, and the quality of my riding is beyond what I ever thought I was capable of and I’m sure I’m not even halfway there yet! Learning from such great people has been invaluable and I look forward to continuing to work with them and others great minds over the coming years. I am excited to put this winter’s work into some serious practice next season with some big goals and even bigger dreams.

EN: What is some advice you would give to an up and coming rider who wants to succeed?

CO: It has been tough; it is still tough, and I have no doubt with will continue to be tough. But our determination and pluck and perseverance are what makes us event riders so impressive and strong. It has been a rollercoaster already, but my passion and drive has never wavered and I can’t wait to see what the future has in store. I know it is going to be difficult and some days I will want to give up but what is the point in spending all day everyday sweating over a job you don’t even care about? I would never be able to forgive myself if I didn’t give my dream a go and what’s the harm in trying? At least I can say I gave it a bloody good go!

EN: What will your business look like?

CO: I am looking to develop event horses, provide private coaching and work with owners to compete horses at any level in 2021 and beyond. I am a qualified BHS stage 3 coach, currently working towards my stage 4 exams (COVID permitting!).
I will be available in the southwest area for private lessons for clients of any age or ability; I am able to travel to you or make arrangements for premises. I will also be available to provide clipping, plaiting and show prep services in the Sturminster Newton area.

I have four stables available at William’s yard for all kinds of horses and their needs. I am rather short – as I am often reminded – so am able to take on rides on ponies as well as bigger horses. I would happily accept rides on any horses in varied types of work/discipline/age/ability. I am a competent hunter as well as competing in lower level pure dressage and show jumping alongside my eventing at novice/intermediate levels. I have trained with Harry Meade, Yogi Breisner and Tim Rogers and will continue to work with them in the future alongside William and his coaches. So, whether you are interested in supporting a young rider looking to make a career in eventing or you are unable to ride as often as you would like or have a young horse that needs more consistent work to develop – the list goes on, and I am happy to offer my services.