By Britney Grover
Portraits by Adrienne Morella
Dudley Macfarlane has been a dedicated horsewoman her entire life, even while juggling her Wall Street banking career and raising three boys. In 2013, she and her horse Authentic won the Washington International Horse Show Adult Amateur Hunter Championship, and last fall she and her “horse-of-a-lifetime,” Roland Park, were awarded the “Automation-Model Cadet” Memorial Perpetual Trophy at the 2018 National Horse Show for the best ride of the Amateur-Owner divisions. Dudley and her husband now live at their own Mount Fair Farm, a historic property near Charlottesville, Virginia. At 64 years old, Dudley still hasn’t grown out of horses. “Ever since I was about 16, my mother kept saying, ‘You’re going to grow out of it, you’re going to grow out of it,’” Dudley said. “Then I got married and had kids, and she still asks me to this day, ‘When are you going to grow out of it?’ And I say, ‘Mom, you’ve been on my case for 45 years. Haven’t you figured it out yet? I’m not. It’s not happening.’ It’s in every fiber of my being; I feel at peace when I get on a horse.”
When did you first become interested in horses?
I’m not really sure; I’ve always loved them. My mom grew up with horses in Virginia where her father owned a sale barn, so she rode as a child and through high school but stopped riding before she went to college. It was always just a part of me; I played with little toy ponies, and I started riding when I was about 8.
Did you show growing up?
I grew up in Atlanta and it wasn’t really very horsey back then, but I did show. I did the large ponies and then I moved up to the junior hunters. I never owned a horse; I leased my pony and I leased my junior hunter. I went to Hollins University specifically so that I could ride. We did a lot of foxhunting, and we did a lot of local shows where you would take one of the school horses from Hollins and show them at regular shows in the adult hunters. My senior year, I did do a little of the intercollegiate. It was so brand new it wasn’t anything like it is today, but it was fun getting on strange horses, going into the ring and riding whatever you had, whatever was underneath you.
When did you get your first horse?
I graduated from Hollins in 1977, got married right out of school and lived in Charlottesville for two years while John was in business school. I rode some there, I did some catch-riding for a woman named Connie Dempsey who had a bunch of Thoroughbreds she would take off the track and teach them how to foxhunt. Then we moved to New York City, and riding sort of got put on hold; every once in a while I would lug my saddle up to Central Park to a place called Claremont Stables, get on one of their horses and gallop around the park. I was working on Wall Street so I had very long hours, but after about two years of that I looked at John and finally said, “I think it’s time I get a horse.” We moved out to Westchester County and I bought my first horse with my first bonus check from my job at Citibank in the municipal bonds department.
How did you balance work, riding and starting a family?
It wasn’t easy, but if you want something badly enough, you’ll do it. I’d leave the house about 6:00 every morning to commute from Westchester County to Wall Street and put in a full day, leave Wall Street around 6 p.m. and take the train home. I’d have my riding clothes in my car, jump in the car from the railroad station and go up to a place called Coach House Stables, and I would ride at night by myself in the indoor ring. In 1985, my first son was born and by that point we had moved to Connecticut so I started riding at Ox Ridge with Scott Stewart. That’s when I really got more invested in the whole thing, and I started getting my first amateur-owner horses.
I rode with Scott for eight or nine years and then Scott decided to spend more time in Florida and I wasn’t willing to travel to Florida with my three boys at home. I started riding with Jimmy Toon in South Salem, New York; he stayed at home mostly and everything worked out great. I would show in New York and Connecticut and freeze to death throughout the winter, but I needed the points to get to Devon and Indoors. Then in the spring there were the really nice horse shows in the area, you had the Old Salem Horse Shows, Ox Ridge Horse Shows which I actually ran for about 10 years, and then you had the Hampton Classic, Fairfield, Lake Placid and Vermont. So at the time I just stuck it out and froze riding up in New York for the nine years I rode with Jimmy.
What brought you to Virginia?
I always had a dream that I wanted to own a horse farm in Virginia, and fortunately my husband was kind enough and stood behind me in moving back to Charlottesville. We moved permanently about four years ago, so now we have our own farm. We have a 15-stall barn, which we built; we built an outdoor ring, we have a nice indoor ring, lots of fields to ride in, and we’ve bred a lot of horses. I probably have five or six home-bred — some of them have been successful, some of them not so much, and I now ride with Rodney Bross. He’s helped me so much — it’s been incredible how much I’ve learned at an older age.
How did you come to develop Mount Fair Farm?
When I came to see Mount Fair Farm for the first time in 2003, I looked at the house, walked up the front steps and opened the front door — I didn’t even have to go in. I said, “This is it.” When we first bought it, all it had was a house and two dependencies, one that used to be the icehouse and one that used to be the smokehouse, on 78 acres. The house we live in now was built in 1848; we were still living in Connecticut at the time but we started renovating it. We had to be very careful about what we could and couldn’t do to the house since it’s on the National and Virginia Registries of Historical Places, so it took several years.
We ended up building a seven-horse barn because originally I thought it would be a place where we would just keep the retired horses. But the more time we spent down there, the more we realized this was really where we wanted to be. We outgrew the seven-horse barn and added another eight stalls to it, and we’ve been adding property so we now own close to 1000 acres. We’re very fortunate; I’m very fortunate that my husband’s been able to get on board with my passion. Every time I got pregnant he’d think, Okay this is it, she won’t want to ride anymore. But I’ve always been able to fit everything in.
Has any of your family shown interest in horses?
My husband has learned a little, I’ve taught him how to ride. We’ve had a couple of nice horses for him that he could play around with, and my youngest son, Brian, is a very good rider. The moment he sat on a horse, I said, “Wow, you’ve got a future here!” And he loves it. They get on the horses and they’ll just trail ride, and I’ll give Brian a lesson every once in a while, but we’ve had the most fun doing equestrian safaris. John just wanted to ride well enough to do a real equestrian safari in Africa; he and I have done that four times, and Brian did it with us once. We usually go to Tanzania. It’s just remarkable; to be out in the Serengeti, to go at a full gallop and have zebras and warthogs and giraffes galloping along with you is absolutely amazing.
What are your goals at this point?
To be champion or reserve at Washington or Kentucky would be really amazing — I’ve shown there with Roland Park and I get maybe two points away from it; I get so close and then I make an error. But you know what? I really just want to be able to keep riding: I’m 64 years old, and I still do the 3’6″ amateurs. I have a 4-year-old that I’m just starting to show in the adults, and it’s quite amazing that I can take a 4-year-old who’s never been off the farm and do that. I just want to be able to keep showing, having fun and being able to get in the saddle every day. I love to jump, and I don’t think I’m going to be satisfied just trail riding at the farm in my golden years, although they’re approaching much more quickly than I like to admit. But I still feel good, I’m still brave enough to do it, and I’ve got really good horses underneath me, and I think that’s a tribute to Rodney as well as his training — he’s instilled a huge amount of confidence in both me and the horses.
For more information, visit mountfairfarm.com
Photos by Adrienne Morella, www.adriennemorella.com, unless noted otherwise