Instruction and Training

If you want to compete or improve your skills, regardless of whether you bring your own horse or ride one of Winchester’s, the talented trainers and instructors will tailor a strategy to get you where you want to be.

Winchester offers lessons for all ages and abilities. Bring your own horse or ride one of our safe, experienced school horses. Contact us to learn more.

KemPlantation**Bevin O’Reilly Dugan
Manager/ Head Trainer

Bevin Dugan, of O’Reilly Equestrian, has been completely devoted to horses since she began riding at nine years old. She began riding at King Oak Farm in her hometown of Southampton, MA, and thus began her love of horses. The exposure to eventing and dressage Bevin received in her days at King Oak stuck. She continues to favor those disciplines, though she has had experience in other disciplines as well.

Bevin is an active competitor and devoted trainer and instructor. She currently competes at the CCI** level of eventing and has competed through Third level in dressage. Bevin is also a USEA ICP Level 2 Instructor and USDF Bronze Medalist.

Teaching is extremely important to Bevin. She places as much emphasis on how she teaches as she does what she teaches, realizing everyone learns in a slightly different way. She places a strong emphasis on the rider’s position in order to have clear communication with the horse and make sure the rider’s focus is always on telling the horse what to do and never what not to do.

In working with the horses, Bevin works to make sure horses understand what is being asked of them and that they are using their bodies properly in their work. She believes that proper management is extremely important to the training process. More than good riding goes into producing horses properly.


tess_delenTess Winterling

Tess Winterling is certified as a Centered Riding instructor, currently holding a Level II certification. She also competes in dressage, recently earning her USEF Bronze Medal with her horse Delen.

She has introduced many horses to showing in many disciplines including: dressage, hunter, pleasure and low level eventingFor several years, Tess has held and taught fun filled summers camps for young riders of all ages, as well as assisted in running an entry level eventing camp.

Tess began fox hunting with Guilford Hounds when she was 14,  earning her colors in 2006, and becoming a Master of First Flight in 2005.  Tess has started numerous horses in the hunt field for their owners.

She has participated in, assisted with and demonstrated for Centered Riding clinics with Sally Swift, Lucile Bump, Karen Irland, Deb Moynihan, Sam Morrison, Sally Bauder, Sue Harris, Jamie Wallace, Mitsy Summers and others. Other instructors which Tess has trained and continues to train with, include: Tom Nagel and Karen Irland (Riders Seat), Classical Equitation with Francois Lemaire de Ruffieu, Bob Jeffries and Suzanne Shepard’s Partnership Training, Jerry Schurink (Cavaletti), Joy Congdon (GMHA) and Suzanne Mente(Dressage).

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Winchester Stables
336 River Road · Newfane · Vermont · 05345 · USA · (802) 365-9434