Often seen riding sidesaddle behind hounds when she’s not designing fine jewellery, Philippa Holland's love of racing inspired this month’s Dianas of the Chase race

Often seen riding sidesaddle in the hunting field, when Philippa Holland discovered you can only ride astride in point-to-points she decided to create a race of her own. The Dianas of the Chase race now runs biennially, and is on again this December.

Our sporting Dianas column celebrates seriously sporting ladies and offers advice and encouragement. For more, stalking is Bryony Daniels‘ passion – and the Highlands have her heart. And sport is very much a family affair for Lady Melissa Percy, who has just launched an outdoor clothing line.


My hunting life began, aged eight, when I was given a pony on loan from some family friends. Having been born to non-equine parents it took a lot of persuasion. My New Forest pony was 21, had hunted all his life and carted me about the Hampshire and Garth South country in Thelwell style. Soon I loved it as much as he did.

Later, staying in Normandy with Venetia Wimborne, a boyfriend’s mother (and about the most elegant lady on or off the hunting field to walk the planet), she gave me a beautiful tweed habit to wear and popped me up on her old hunter sidesaddle and off we rode through the forest. Oddly, it felt easier than I ever imagined and so, inspired by Venetia, I was hooked.

Back in England, the family introduced me to the Quorn (Venetia’s previous husband was the renowned Captain Fred Barker, who had mastered the pack for 16 seasons). Before long I had joined forces with Martha Sitwell, who was also riding sidesaddle. We became obsessed with researching the history of sidesaddle and the brave and daring ladies who had been figureheads of their time, and started taking lessons with Roger Philpot, who taught us the importance of correct balance and a correctly fitting saddle – and also never to talk to a man from the “near side” when out hunting.

At this time there were only a handful of ladies riding sideways on the hunting field keeping up with the rest, jumping gates and hedges. After the Second World War side-saddle had really been replaced by riding astride – perhaps a sign of women’s liberty or perhaps the decline in household staff (cleaning of habit/saddle is fairly labour intensive) – and sidesaddle was rarely seen outside the show ring. Martha and I decided we wanted to break the mould and take sidesaddle back to its roots. Martha, with her innate sense of style, started to design riding habits under the name Sitwell & Whippet. We had them made up by a Savile Row tailor. They were beautiful and unique and broke the rules of what a habit should be.

I kept two horses in Leicestershire and enjoyed the magical Shires for three seasons, driving up and down from London and staying with friends near Market Harborough. Leicestershire may have changed a fair bit since the days of Captain Fred but there is still endless old turf, fly hedges and hunting officers to open gates and give you a lead, making it the perfect place for sidesaddle.

Having ridden in a few charity races I was asked to ride in the Magnolia Cup at Glorious Goodwood (a ladies-only five-furlong race). It was the most amazing experience, not only riding out and training but the thrill of being catapulted five furlongs up the Sussex Downs towards a crowd of 25,000 cheering in the Grandstand was pretty exceptional. I was fortunate enough to be given some amazing horses to ride and we all wore colours designed especially by well-known fashionistas. (When I subsequently rode in the odd point-to-point members race it felt comparatively slow.)

After three seasons in Leicestershire I rented a cottage in Dorset and hunted with the Dorset packs, mainly the Cattistock and Blackmore & Sparkford Vale. Dorset has so much good hunting country and it is hugely varied. With the Cattistock you could be on the coast, in the vale or in hill country. The hedges take a bit of getting used to as they are vast, normally with huge drains. Also, the ground is a lot softer than Leicestershire so riding sidesaddle can be tough on the horse (as you can’t get up off their backs). Having said that, there is no better feeling than flying those hedges sideways – although I recommend a pilot who knows the country well (think Bay Middleton).

One thing led to another and with added excitement and confidence (it’s quite hard to fall off sidesaddle), I started to imagine riding sidesaddle in a point-to-point. God knows why because at that point I’d never ridden in one astride. Sadly, it was only after buying a retired chaser, Zanzibar Boy, that I found out the rules had changed in the 1960s and it was no longer possible to ride sidesaddle in a point-to-point. Cine film of ladies pointing sideways in the early-20th century looked so glamorous and wild, too, epitomising the true spirit of Diana the Huntress.

Hence the idea to recreate this race was born. As I was a subscriber at the time to the Quorn, Joss Hanbury suggested that Brian Henton might host the race at his home, Ingarsby Old Hall – an ancient hunting estate in Leicestershire that once belonged to the Earl of Warwick. So with the help of the Household Cavalry and our sponsor at the time, Bernard Weatherill, the first race was held. It now runs biennially and we have entries from Ireland, America, France and Britain.

TOP TIP: The golden rule to sidesaddle is keeping your right shoulder and hip back (sitting straight in the saddle). I’ve been practising yoga since I was 18 – so, yes, a daily yoga practice helps with flexibility, balance and core strength.

This year’s race, sponsored by Dodson & Horrell and Laurent-Perrier, is on 10 December at Ingarsby Old Hall, Ingarsby, Leicestershire (dianas-of-the-chase.com)