Head Coach and Trainer 

Jenna Rogerson is a highly skilled equestrian professional, well respected for:

  • Coaching riders who compete on the “A” Circuit (National Gold) Level in Hunters, Jumpers and Equitation

  • Producing riders who consistently finish in the top ten of the OHJA standings and compete at the Royal Agricultural Winter Fair Annually 

  • Her high standards and professionalism

  • Having extensive training from World Cup and Grand Prix competitors

  • Continuing to train with top-level equestrians—being committed to continual improvement

Jenna began her riding career with a passion for horses when she was five years old. Even at that young age, she knew this was more than a hobby – it was her life’s work.

Like any keen equestrian she started lessons at a Local stable. At age 10, she moved to Southern Cross Stables in Windsor, Ont. There, she progressed steadily through the ranks of Pony Club and the Trillium Circuit, training with Jonathon Chestler, a former Grand Prix rider. She later began to compete at Trillium and “A” Circuit shows.

In 1998, she purchased her own talented young mare. A year later, introduced to dressage, Jenna began to train with Heather Buchner, a successful member of the Young Riders Dressage Team. Under Heather’s guidance, Jenna worked her way up the National Junior levels. Throughout this period, she participated in many clinics with Grand Prix riders and trainers Gillian Sutherland and Bill Challis, which thoroughly prepared her and her horse to compete successfully up to Medium Level. 

After a chance introduction in 2002 to Jane Laframboise, a Level 2 USEF hunter/jumper coach, Jenna found her way back to the hunter/jumper world. Jane saw hunter potential in both Jenna and her young horse. Together they trained for the 2005 show season to compete in Adult Amateur Hunters. Throughout the winter Jenna competed at competitions in the U.S. while preparing for the Ontario “A” Circuit that coming summer. 

Next, Jenna embarked on learning how to produce winning hunters and jumpers on the “A” Circuit. She took a position as head FEI groom and barn manager for Margie Gayford, a successful Grand Prix jumper, at Wingberry Farms in King City, Ont.  For two years Jenna and her two horses worked alongside Margie as well as Margie’s father, Tom Gayford, who was a gold medalist in the 1968 Olympics in Mexico City. Through handling every aspect of managing a show stable—from minor to significant—Jenna seized the opportunity to learn all about caring for and training show horses at the elite level. She gained invaluable knowledge and experience throughout her time at Wingberry.

During this time, Jenna had the opportunity to travel North America to many top “A” Circuit shows such as Winter Equestrian Festival, Aiken, Atlanta, Quebec, Collingwood, the Royal and Spruce Meadows, multiple times. She spent countless hours watching ringside, walking FEI-rated and World Cup courses, and discussing different scenarios and training methods with many upper level riders and trainers. This gave Jenna insight into elite level competition and training. In working with these high level equine athletes Jenna also had the opportunity to learn from many elite Equine health care professionals. Knowing how to care for horses properly is just as important as training them. 

All this experience has made Jenna an exceptionally well rounded, knowledgeable coach and trainer. She believes that all riders need a strong training program based on solid foundations. As well, her studies in psychology at the University of Windsor enable her to help manage high-level athletes by incorporating sports psychology and coping mechanisms into their programs.

Jenna currently owns and operates Skyland Stables in Utopia along side her fiancé Andrew and two girls, Isabella and Sienna who both ride as well. Skyland offers boarding, training and sales services.  The facility is equipped with all amenities including an indoor arena, outdoor arena, grass turnout, hacking and two new barns. While she does ride, show and train herself, her passion is coaching and working with young athletes who demonstrate a strong passion for the sport.  

Jenna currently has students and horses showing successfully on the “A” Circuit in both core and non-core divisions from the Short Stirrup Division up to the Junior/Amateur Jumper Divisions. Many of which qualify annually for the Royal Agricultural Winter Fair. 



Assistant Trainer and Coach 

Jenna Fines works closely with Jenna Rogerson to ensure that all horses and riders at Skyland receive the best training and instruction possible. If Jenna Rogerson is away at horse shows with clients Jenna Fines is often available to ride any of that sales of training horses that remain at the home farm so their education does not go on pause during our busy season. 
Jenna has a very extensive background in developing and breaking young horses and introducing them to competition. She has worked at breeding and show facilities and has competed herself on the “A”Circuit in all rings. 
Her methodical approach to teaching and her well rounded educations makes her an incredible asset to our Team at Skyland. 
Jenna Fines also currently runs our Competitive Development Program. Due to her extensive experience within the industry  and riding competitively herself for many years she offers great insight into the world of competition. For more information on this program click below. 



Operations Manager/Working Student 

Paige has had a love for horses since she was 7, and started lessons at a local farm in Tottenham. She has been a member of the Skyland family for almost a decade. When Paige joined Skyland she leased a large pony and began showing with us in the children’s pony division when she was 14. 

The Trainers at Skyland saw a great amount of natural talent and drive in Paige. Shortly after joining Skyland Paige was offered a position as a Working Student.  She worked for 5 seasons full time and year round part time. Following that while Paige was still a junior she was hired as Head Groom to assist Jenna in managing the day to day operations of the farm which included training, riding and showing Skyland’s horses as well as clients horses and she also oversaw all aspects of daily care. 
Paige had a lot of success as a junior in the ring. Not only did she take multiple thoroughbreds off the track and retrain them into competitive hunters on the “A” Circuit, but in 2016 she also qualified Calista, a lovely green mare by Cabardino, for the Royal Winter Fair in the very competitive Working Children’s Hunter Division. 
Since her days of competing as a Children’s Hunter Paige continues to be a vital piece of our teams success at Skyland. Not only does she regularly ride her own horses but she also catch rides at competitions on horses owned by others as well and consistently produces winning results. 

Paige currently attends the University of Guelph full time in the Bachelor of Science program with a major in animal biology. She will be entering her fourth year this fall. During the summer she is a vital part of our show staff, making sure nothing is forgotten, entries are completed and our horses and riders are perfectly turned out and prepared for the ring.