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Town and country lifestyle

Jock and Penny MacKillop, along with their parents and children have created a premier stable in the heart of Terrey Hills.

(Photos © Carol Gibbons Photography)

Jock and Penny MacKillop, along with their parents and children have created a premier stable in the heart of Terrey Hills. It has enabled their children to become completely immersed in a rural lifestyle, developing into championship riders on the competitive show jumping circuit. Less than 35 minutes from Sydney’s CBD yet a world apart, it's been home for this extended family for more than 30 years.
A fast moving thunderstorm has just made its way through the Northern Beaches, soaking Jock MacKillop’s five acres and giving an extra sheen to the gently rolling landscape dotted with paddocks, grazing horses and a sprinkling of chickens. It’s a breathtaking spot and when the low hanging fog clears, the elevated vistas stretch from St Ives to Asquith.

Tucked well away from any main roads, ‘Highgrove’ lies within the heart of Terrey Hills, less than 35 minutes from Sydney’s CBD yet a world apart. Home for over 30 years, the northern part of Warringah Shire, Terrey Hills is fast becoming a suburb that many residents in the North Shore are now hearing about. The perfect combination of proximity to the city, top-notch private and public schools plus perhaps the lowest residential density per acre in Sydney has made it a very attractive alternative to those longing for a more tranquil, rural environment within easy reach of the city and beaches.

Originally from a waterfront home in Mosman and a graduate of Scots College, Jock’s determination to spend every waking moment around horses saw him gravitate to the area in his teens. In 1987 fortune smiled upon him in the form of Penny Caspar, a dressage competitor whom he met at a party at the very same property where they now live. 27 years later, Jock and Penny, their kids Steph and Riley and Penny’s parents, Dennis and Andrea have created a premier stable that trains, boards and breeds; in the process, they have enabled their kids to become fully immersed in a rural lifestyle, with each one developing into championship riders in the ultra-competitive show jumping circuit.


Now 18 and studying for her HSC, Steph is taking a short break from the daily rhythms and routines that have shaped her life since she was small. She is typically up with the first light, exercising the horses before breaking off for a full day at Northern Beaches Christian School and then back at it again until dark. The deep sense of responsibility she feels towards ‘Team MacKillop’ as the family enterprise is known, is remarkable and has given her a focus and discipline that’s quite unique for her age. Steph is expecting to study Animal & Veterinary Bio Science at Sydney University next season, reckoning that as a researcher, she will be able to continue her jumping career anywhere in the world.

Riley, at 16, shoulders the same responsibilities as his sister and has had tremendous national and international success, winning the coveted World Championship FEI in Bogota Colombia in 2012-2013. Making that win all the sweeter was the fact that he was on a borrowed horse – one, that by the rules, he was only able to ride for half an hour prior to the competition. Jock’s view of his children’s achievements is pretty straightforward, “the kids had to work for everything – nothing was given to them; the fact is that either can take a mediocre horse and make it a champion – that’s the real test of expert horsemanship. ”


Weekends are spent at various competitions up and down the east coast from Melbourne to Queensland; an integral part of ‘Team MacKillop’ are the half dozen people who take over the daily responsibilities when the family is on the road, along with Penny’s parents, who own the property and built the original home there. One of the biggest draw cards for the family is the opportunity for three generations to work and live together, a rarity in this day and age. Terrey Hills and Oxford Falls still offer that possibility, harking back to a time when life was just a bit less frenetic and the summers seemed endless and full of fun.