The Horsemanship Behind Gabby Dickerson’s Kentucky 5★ Journey

When Gabby Dickerson steps into the start box at the Defender Kentucky Three Day Event 5★, it will be the culmination of nearly two decades of deliberate, disciplined horsemanship. The 30-year-old eventer from Gordonsville, Virginia, isn’t chasing a moment — she’s built a whole career to earn one.

At GreenHorseBrands, we’re drawn to athletes who put their horses first. Gabby is exactly that kind of horsewoman, and her story holds real lessons for anyone serious about performance horse care — from the mentors you choose to the horse bedding in your trailer.

The Foundation

Horsemanship Learned From the Best

Gabby’s path to Kentucky began at age 11 on the hallowed grounds of the Kentucky Horse Park, where she first worked alongside U.S. Olympian Kim Severson. By 12, she had left her family home on North Carolina’s Outer Banks to train with Kim full time — an equine education, as her parents put it, long before online schooling became mainstream.

At 17, she crossed the Atlantic to work with British Olympian Nicola Wilson — a move that started, like so many great partnerships, with a single clinic. “I could just tell she was going to be a great person to spend time around,” Gabby recalls. That instinct proved right. She then had shorter stints working for German legend Ingrid Klimke and Olympian Dirk Shrade before returning to the United States at 20 to start her professional career.

That depth of international exposure shaped not just Gabby’s riding, but her entire philosophy of horse care. European horsemanship tends to be methodical and horse-centered, and those values are woven into everything she does at Milltop Farm in Virginia today.

The Partnership

Building “Ken” — Horse Development Done Right

Gabby’s Kentucky partner, Traditionally Fernhill — known around the barn as “Ken” — is a 12-year-old Irish Sport Horse she acquired in early 2024. He arrived with a single 4*-Short outing to his name. Rather than rushing him, Gabby leaned on everything she had learned: systematic conditioning, expert coaching, and an unwavering focus on the horse’s readiness over competitive ambition.

The results speak to her horsemanship. Ken delivered an 8th-place finish at their 4*-L debut at Tryon International. The pair then completed a strong 4*-L at Morven Park — a course Nicola Wilson herself called worthy of 4.5★ status. And it was experience gained through Ken that helped Gabby simultaneously bring three other horses to CCI4* level.

That kind of development — patient, principled, and horse-first — doesn’t happen by accident.

Stable Management

Why Gabby Made the Switch to Cardboard Bedding

Great horsemanship doesn’t stop when the saddle comes off. Gabby’s barn management reflects the same careful thinking she applies in the arena — and it’s why her switch to cardboard bedding is worth understanding.

Gabby has since transitioned all of her Advanced horses onto cardboard bedding. Her reasoning is straightforward, and it echoes a growing awareness across the eventing and jumping worlds: respiratory health is performance health.

This is particularly relevant at the 4* and 5* level, where horses are asked to perform at their aerobic ceiling. A horse carrying even subclinical airway inflammation is a horse that cannot perform to its true potential — and conventional bedding, with its dust and organic particulates, is one of the most common and overlooked contributors to respiratory compromise.

Cardboard bedding addresses this at the source. Made of pre-consumer cardboard, Airlite has dramatically less dust and other microscopic particles that trigger airway inflammation. For performance horses stabled for long hours between competitions, the difference in air quality adds up over a season.

The Full Program

Simple, Consistent, Horse-First

Cardboard bedding fits naturally into a management philosophy that Gabby describes as deliberately uncomplicated. Her horses spend as much time outdoors as possible. Each day typically opens with an hour on a free-walker by Kraft — a smooth, flat rubber surface that provides low-impact movement in both directions, similar to European-style roadwork.

Supplementation is kept minimal. “We’re not giving a thousand supplements because they get what they need through good feed,” she says. “We keep everything as high quality as we can regarding their care, then ride them as correctly as we can.”

That simplicity is a deliberate choice. Consistency, she believes, is more powerful than complexity. And the decision to optimize the basics — air quality through cardboard bedding, turnout, low-impact conditioning, quality nutrition — reflects a holistic view of what horses actually need to thrive.

Looking Ahead

What Kentucky Means — and What It Doesn’t

Gabby is clear-eyed about what she wants from her Kentucky debut. A clean, solid, horse-honoring round. Not a chase for headlines, but proof that the process works. “Of course I’d love to push out a personal best at Kentucky,” she admits, “but I am aiming more for a solid result. It’s a 5★ and anything can happen.”

That measured confidence, earned through years of careful horsemanship, is exactly what makes her and Ken a partnership worth watching. They are not a shortcut story. They are what happens when horsemanship — in the ring, in the barn, in every bedding and management decision — is taken seriously for a very long time.

At GreenHorseBrands, that’s the kind of horsemanship we celebrate. And we’ll be cheering them on at Kentucky.