By Jennifer DeMaro
Portraits by Melissa Fuller
Whether the day starts out at the gym boxing or in the arena riding, Ali Wagstaff approaches her daily routine with a winning attitude. In the spring of 2020, she started Mill Pond Farm in Wellington, Florida, just a stone’s throw away from the Winter Equestrian Festival showgrounds, where Ali teaches her students and horses to become athletes.
The gym plays an integral role in Ali’s success. “As a professional athlete, I hold myself to standards congruent with my career,” she said. She attends a local gym, Fight Fit Wellington, where she does strength training, cross training, conditioning and recovery work to improve balance and mobility. Her boyfriend, Patrick Parsons, is the owner and head coach of the facility, so slacking off is a bit more challenging. Being present and accountable has helped Ali with her fitness journey. “I can’t stress enough the improvements in my athletic ability since I started treating myself like a professional athlete and not just a rider,” she said. This philosophy carries over into her horse training. “When I ask any of my equine athletes a physical question, I want them to be as physically prepared as possible to respond to my aids.”
Learning to Ride
As an only child, Ali had the full attention and support of her parents on her equestrian journey. “My father’s family had ponies and my grandmother even taught one of our Olympic-level dressage riders, Tuny Page, how to trot as a little girl,” she said. Ali had strong roots to grow from to become the successful equestrian she is today. From the first time on a pony ride at the age of 2 she spoke the words every parent should probably be afraid to hear, “I want to ride ponies and jump!” 
Pony rides progressed to lessons and then escalated to showing. She got her first pony at the age of 7 and has never known a day without horses since. She has fond memories of her parents being there for every step she’s made. “My dad had a trailer and shipped the horses to shows, where he videoed or photographed all my rounds, and my mom organized every detail to make sure I looked the part,” she said. Her parents are still an integral part of her life as they live nearby in Wellington.
Instead of remembering their first boyfriend or girlfriend, horse people tend to remember their first pony or horse, and Ali is no different. “My first walk/trot pony, Benlea Penny, lived with me for her entire life and produced five beautiful foals,” she said. “My second pony, Wit’s End Day Dream, brought me success in the ring at Pony Finals and we won champion and reserve ribbons at almost every show.”
Unfortunately, ponies are eventually outgrown and the journey to horses begins. Ali attributes her growth as a rider to being a catch-rider. “My first Junior jumper horse, Truman, was 15.3-hands and this is when I learned the saying, ‘It’s the size of the heart, not the horse, that matters.’” One of her Junior rider achievements was being ranked in the top 20 at USET Showjumping Talent Search Finals. Her next horse, Wynonna, was Ali’s first 1.40m horse. “Riding her was like trying to hold back an avalanche, and I hold a special place in my heart for her,” Ali said.
First Grand Prix Win
They say a picture is worth a thousand words, and Ali found herself buying a horse off a photograph from an auction in Europe in 2015. Generaal came to the United States as a 4-year-old and proved to be a great acquisition by winning circuit champion in the 5-Year-Old Young Jumpers at WEF in 2016, and the USHJA National Hunter Derby in 2021. “Generaal is a very special horse to me because he is a confidence builder for my students and one of the most intelligent horses I have ever had the privilege to work with,” Ali said.
Generaal’s win in the National Hunter Derby was followed up by what Ali says is her most memorable win in her career so far. “Winning my first Grand Prix in the summer of 2021 was without a doubt my most memorable, not only because it was my first Grand Prix win, but because I had also won the USHJA National Hunter Derby in the same week,” she said.
This past spring Ali bought her current competition horse, Great Thing—who is related to Generaal, both descendants of sire President. Up until this time in her career, she’s ridden horses that are very willing to learn. “This horse is different; she’s a fierce competitor who has taught me how to win, which has been an incredible skill I’ve recently added to my repertoire,” Ali said. Her wins with Great Thing include both $10,000 1.40m Stake classes in the same weekend at Equestrian Sport Productions last June. It takes a team to succeed, and Ali gives credit to her current coach, Monty Kelly, and the whole team from Stepping Stone Farm for setting her and her horse up for show ring success.
Teaching to Win
Ali always starts her first lesson with a new student emphasizing the importance of communication between horse and rider. “As riders we need to tailor our communication and expectations to match their cognitive abilities, and more importantly, how they perceive and make decisions based on the stimuli we impose on them,” she said.
Since horses are herd animals, Ali teaches the importance of communication and instilling in them the importance of communicating with horses in their own language without expecting them to learn ours. Ali credits one of her first trainers, Charlie Moorcroft, for her teaching style and training philosophy. “He taught me everything I love about horses and riding,” Ali said. Charlie is known for giving kids the confidence needed in the early stages of riding, and Ali got that confidence and ran with it.
Of course, Ali wouldn’t be where she is without the founders of her life and support group: her parents. “I owe everything I have to my mom and dad,” she said. “My mom always makes sure my horses and I have everything we need before, during, and at the end of every day, from clipping to tacking, wrapping and clapping, she’s always there for me with the exact right thing in each moment, like magic! I would not be the person I am today without the unwavering support of my amazing parents.”
Free time is sparse for Ali, but when she has it, she loves fishing with Patrick. “As captain of the boat, I oversee finding the best fishing spot and Patrick takes care of the rods and tackle,” she said. Though she loves to fish, she is not a fan of being in cold water. Ali used to tell people she wanted to be a dolphin trainer when she grew up but the thought of cold water derailed that career path. “Horse trainer is a great substitute, especially living year-round in Florida, with plenty of sun to keep me warm!”
Ali has a degree in clinical psychology which she has been able to put to good use. “I’ve been able to follow my passion using what I’ve studied to help me with the behavioral training aspects of this industry, as well as skills related to working with many different types of people,” she said. “For those who want to ride, I teach riding, and for those that want to compete, I teach how to win.”
Ali likes to keep challenging herself and has a future goal of being a professional course designer. “I would someday like to be one of our industry’s respected course designers,” she said. She has put that goal on hold until she can dedicate herself to learning the craft. In the meantime, Ali loves designing courses in her own arena for her students and horses.
Ali is excited to continue growing her business by helping riders and horses develop the confidence needed to succeed. Both horse and rider benefit from Ali’s win-win attitude. “Every step taken on a horse is a step in the right direction,” she said.
For more information, visit www.millpondfarminc.com
Photos by Melissa Fuller, msfullerphotography.com
