Our Riding Instructors

Sydney Ennis

Sydney Ennis

I have been riding at Fairwinds since 2007, and competitively showing since 2010. I started out with  hunter/equitation for two years, then started eventing.I have been working at Fairwinds since I was 13 years old, and now work here full time. I like to be creative with my lesson program, so my students have fun!

I have been taking lessons from the Bowersox family for the past decade. I am currently competing locally in eventing, and have successfully competed novice level with my eyes set on Training with the Thoroughbred I lease from an upper level eventer.  I also coach and train the event/show team here, fulfilling my lifelong dream of taking kids to their first shows and events, and exposing more people to eventing.


Robby Bowersox

I have been riding since I was 10 years old. I started out with hunter shows hosted by Fairwinds, and then joined Pony Club where I learned to event. I have competed at Pony Club Nationals for the sport of Tetrathlon. In the summer of 2011, I competed at nationals and won my division. 

I have trained with Judy Thayer, Bruce Davidson and currently train with Sally Lofting, focusing mostly on show jumping. In my lessons, I incorporate the fundamentals of dressage, show jumping, eventing and equitation so my students become well-balanced riders.  And of course I make sure we have fun while learning!


Mandy Myers

I began my riding career at the Fairwinds Farm summer day camp, and I never looked back. My discipline of choice is eventing, which is a very diverse genre of riding that includes dressage, cross country jumping, and stadium jumping. I have trained with Jen Facciolo, Judy Thayer, former CCI** eventer Monica Fiss,

and CCI**** eventer Erin Sylvester.  I believe that it is extremely important that I continue to be a student and improve my own skill in order to successfully teach others.  I seek to expose students to all that eventing has to offer, prepare them for the hunter riding discipline that Fairwinds currently favors, and of course try fun things like riding bareback!