Ashley Madison began riding at the young age of five in Sebago, Maine. She quickly developed a love for dressage and trained under Tanya Rennie. Ashley attended college at Johnson & Wales University, while also dedicating her time as a working student for Olympian Tina Konyot. While there, Ashley had her first experiences riding FEI horses. She then went on to work for Scott and Susanne Hassler at Hilltop Farm in Mayland before traveling to Wellington with a working student position under Olympian Courtney King-Dye.
Thanks to her time working with the top in the sport, Ashley soon became a successful trainer in her own right, in addition to producing top results with her own mounts, including earning her USDF Gold Medal with her own Lugano. Ashley specializes in producing young horses and developing them through Grand Prix. Ashley has notably competed at the FEI levels in multiple Regional Championships, in the USDF Four Year Old Division and Dressage at Devon. In 2017, Ashley was selectively chosen as a rider for one of Carl Hester’s two US symposiums with her own Lugano. The next year, Ashley was chosen as one of only five athletes to ride with Charlotte Dujardin on a 4-year-old training horse. Outside of her own riding, Ashley has developed a loyal following of students that have all progressed in their training, riding everything from newly-backed young horses and eventers to FEI horses. She currently operates Yellow Wood Dressage out of Chesapeake City, Maryland.