Training Built Around Your Progress

Not a Rotation of Staff

At Bayboro, every lesson and training ride is taught by our head trainer — never a working student. When you or your horse are in training here, you're working with a qualified, experienced professional every single time, not whoever happens to be available that day. It's a standard we hold ourselves to because consistency actually produces progress. 

Lead Trainer: Jerry Dean

Jerry Dean is a USHJA Certified Trainer with more than 25 years of competitive show jumping experience, including success at the 5★ international level, along with a strong foundation in eventing up to Training Level. Beyond his own competitive record, Jerry has led his own training business and coached collegiate teams — experience that shows in how he works with riders of every level, with clarity, patience, and purpose.

Jerry's own training has been shaped by some of the best in the sport, including Irish international rider Derek McConnell and Olympian Anne Kursinski. That foundation carries directly into every lesson he teaches at Bayboro.

Guest Dressage Trainer: Cindy Canace, USEF "S" Judge

Cindy Canace is a highly respected dressage professional whose career spans decades of riding, training, and judging at the highest levels of the sport. She is a USDF Bronze, Silver, and Gold Medalist and a USEF "S" (Senior) Licensed Dressage Judge, qualified to judge all national tests through Grand Prix. Cindy brings a rare combination of technical expertise, classical training principles, and a thoughtful, horse-first philosophy to every session she teaches.

At Bayboro, Cindy serves as a regular guest dressage trainer, working closely with Jerry to deliver a unified training program that supports both dressage and show jumping goals — so whatever discipline you're focused on, your horse's foundation stays consistent across the board. We are privileged to have her as part of the Bayboro team.

An Owner Who Trains Alongside You: Brian Healy

Bayboro's training culture starts at the top. Owner Brian Healy has been riding since he was five years old, and that early foundation has grown into a disciplined, lifelong pursuit of mastery. In recent years, Brian has trained regularly with top-level riders including Boyd Martin and Dom Schramm, both of whom serve as ongoing mentors in his development as a competitor.

That commitment extends well beyond the saddle. Brian has pursued extensive coursework through the Rutgers Equine Science Center, the Penn State Extension program, and the British Horse Society — covering everything from safe horse handling and pasture management to first aid and training fundamentals. It's the kind of rigorous, credentialed foundation most owners never bother to build.

It's a rare thing to find a facility where the owner isn't just running the business — he's in the ring, holding himself to the same exacting standard he expects from every trainer on staff. Brian's approach is disciplined and deliberate: study the fundamentals, train with the best, never assume the learning is finished. That standard — precise, demanding, and always improving — is the one every horse and rider steps into at Bayboro.

Your Training, Your Goals

A Program Built Around You

No two riders come to Bayboro for the same reason. Some are working toward their next competition; others simply want to learn, improve, and grow more confident in the saddle. We start by assessing both horse and rider, then build a program around your specific needs and goals — whether that's a lesson once a week or a full training package with rides five days a week. Our head trainer has experience coaching riders and horses of every level and ability.

Training here isn't limited to the arena. Depending on what you and your horse need, it can include behavioral evaluation, dressage and flatwork, jumping progressions, cross-country schooling, and hill work to build strength and stamina — evolving as your horse progresses.

For every training ride, you'll receive text updates and videos, so you stay connected to your horse's progress even when you can't be at the barn.

Our goal is simple: a sound, happy horse and an educated, confident rider — so the progress you make here goes with you.

Clinic Series

Train Alongside the Best in the Sport

Great riding is contagious and at Bayboro, our clinic series puts you in the ring with riders who are shaping the sport at its highest level. What makes our program different is depth of relationship: several of our clinicians aren't occasional visitors, they're an ongoing part of the Bayboro community, returning regularly, getting to know our horses and riders individually, and helping guide our program even between visits.

Our Regular Clinicians

These are the riders our program is built around — the ones who know our horses, our footing, and our riders well enough to coach with real continuity from one visit to the next.

  • International 5★ Event Rider Dom Schramm visits Bayboro several times a year, giving our riders the kind of continuity that's rare to find. Beyond his in-person clinics, Dom remains available for consultation — so guidance doesn't stop when he heads home.

  • International 5★ rider Lillian Heard brings a positive teaching style and a strong record of competitive success, with a particular gift for helping riders build real confidence at every level. She works with horse-and-rider combinations from Starter through Advanced, and her approach makes her a natural fit for our ongoing clinician group.

  • Four-time Olympian and multiple Pan American Games gold medalist, Boyd is a regular clinician and advisor at Bayboro. Beyond coaching, Boyd has been instrumental in advising on the design of our cross-country course — meaning the terrain our riders train on carries his expertise built right in.

Distinguished Guest Clinicians

In addition to our regular clinicians, Bayboro periodically welcomes other top-level riders and judges to supplement our program with fresh perspective and specialized expertise:

  • Phillip Dutton — Olympian, 5★ Rider

  • Peter Wylde — Olympic Gold Medalist

  • Peter Gray — Three-time Olympian, Pan American silver medalist, and FEI 5★ Dressage Judge and Coach

  • Daniel Bluman — International Show Jumping Rider

  • Silva Martin — Nations Cup Gold Medalist

These guest clinics give our riders additional angles on their training — a chance to hear from a different voice in the sport while staying grounded in the consistent program our regular clinicians help build.

Clinic Series

Bayboro regularly hosts clinics with equestrian luminaries such as Peter Wylde, Silva Martin, Daniel Bluman, and Phillip Dutton—bringing Olympians and international champions right to our doorstep. These sessions reinforce Bayboro’s standing as a premier training hub.

2026 Clinics: Anne Kursinski, Lillian Heard, Dom Schramm, Boyd Martin

2025 Clinics: Daniel Bluman, Boyd Martin, Dom Schramm, Peter Wylde, and Peter Gray

2024 Clinics: Stephen Hayes, Boyd Martin, and Dom Schramm

2023 Clinics: Dom Schramm, Emma Ford, Doug Paine, and Stephen Hayes

2022 Clinics: Peter Wylde, Phillip Dutton, Tami Smith, Silva Martin, Kim Walnes, and Boyd Martin