The first time Fred Gilbert walked into the Royal Manitoba Winter Fair, Elvis was an exciting and controversial young performer and the baby boomers were in their teen years.
He has warmed horses up for the evening show by car headlights, next to the now demolished Wheat City Arena, competed in rubber boots at the Manex Arena, when his animals were stabled in racehorse barns and more vulnerable to the weather, saw the first days of the Keystone Centre, and is one of a dwindling number who remember trick rider Buddy Heaton and his jumping buffalo, “Old Grunter.”
Gilbert and his family-run operation, Gilbert Farm, located a mile south of Brandon, marked 60 years of the Royal Manitoba Winter Fair this year, more than half the fair’s 110-year history.
Gilbert grew up attending the fair, watching horse shows from the sidelines of the old arena, now home to Brandon’s police station.
“I got the hook on the smell of the place,” he said. “The shavings and the smell of horses and I just wanted to participate in the fair.”
Family affair
At seven years old, he got his chance. His uncles, Stan and Don Gilbert, bought two horses and decided to try their hand in the ring while their nephew borrowed a pony from a neighbour.
The following year, Fred Gilbert’s mother followed him into the ring, and he was soon joined by his sister, Bev. About 15 Gilberts have taken up the family pastime since then, including Gilbert’s wife, Alice, his daughter, Wendy (now Wendy Gilbert-Armstrong), his son, Derek and Wendy’s two sons, 18-year-old Trace and 13-year-old Parker, all of whom showed this year.
“We have so many great memories and it’s just a great thing to do with your family,” Gilbert-Armstrong said. “We’re all so close together because we do this as a family.”
Read Also
What’s new and returning for Ag in Motion 2025
Every year, Ag in Motion brings the latest in agriculture technology, innovation, farm equipment and industry insights to Western Canada. This year’s Ag in Motion show runs July 15-17, 2025 near Langham, Sask.
For Ron Kristjansson, general manager of the Provincial Exhibition of Manitoba, stories like the Gilberts are a sign of success.
The fair has marketed itself as a family tradition and about 100,000 visitors come every year, many of them familiar faces.
“We’ve got a lot of multi-generational exhibitors that the parents showed and then the kids showed and now the grandkids are at an age where they’re showing, so those kinds of things are very special to us as an organization,” Kristjansson said.
Even among repeat attendees, however, the Gilberts stand out. Kristjansson says Fred Gilbert is perhaps the longest-running horse show exhibitor, although some cattle-showing families might claim the title of longest-running exhibitor overall.
Over the course of decades, the Gilberts have competed in both riding and driving, and have been frequently involved in planning and setting up in the lead-up to the fair.
At the age of five, Gilbert-Armstrong first entered the ring leading a show pony, later moving up to junior driving classes, western pleasure, line classes and gymkhana before returning to what her family’s name has become synonymous with at the winter fair, the Hackney pony.
“As a kid, the classes were all open by size,” Fred Gilbert said. “They went by size, so all the ponies that did all the winning then were pretty well Hackneys. The Hackneys won all the driving classes, so it wasn’t much fun showing my old pinto pony and getting beat by the Hackneys all the time.”
Hackneys arrive
In the ’60s, the Gilberts were approached by their neighbour at the time, Bert Blake, an associate and horse trainer for newspaperman and horse racing enthusiast, John Sifton.
Sifton had been diagnosed with cancer, a condition that would eventually claim his life, and was looking for someone to take his two champion Hackney ponies.
The Gilberts, of course, were interested, but were wary of the price tag with such an elite pedigree. Unbelievably, Fred Gilbert said, the two ponies were offered for free.
“We never taught them: They taught us,” Gilbert said. “They were a very intelligent pair of ponies that were professionally trained and we had a blast with them for many years.”
Now the trainer for Gilbert Farm, Fred Gilbert has watched his wife, children and grandchildren consistently bring back ribbons at the Royal Manitoba Winter Fair.
Lovie Smith, named affectionately after the former Chicago Bears coach, brought Gilbert-Armstrong first-place finishes this year in the ladies’ cart and pleasure driving championship and third in pleasure driving regular competition. Her son, Trace, drove to second in two youth driving events.
Sharp Shooter, another Gilbert Farm champion, claimed the title in three of four events, coming second only in the single harness pony open championship. In at least one instance, Gilbert Farm claimed both champion and reserve champion when Gilbert-Armstrong, driving Clydes Dale, was beat out only by her brother and his horse The French Connection.
“I love it,” Derek Gilbert said. “This is our big show of the year, of course, because it’s our hometown.”
A jockey for the family’s standardbred harness racehorses, Derek Gilbert did not show at the Royal Manitoba Winter Fair until about five years ago, when his father bought a feisty pony from Quebec and asked the younger Gilbert if he would take up the reins.
Accustomed to the much larger, and often equally hotheaded, standardbreds, Gilbert agreed, and has since consistently joined his family both in Brandon and at the many other horse shows the Gilberts attend.
Counting costs
The Gilberts are still devoted to their hobby — and it is a hobby, not business, Fred Gilbert stresses — but the costs of horse showmanship have increasingly been felt. The family once attended between 15-20 shows a year, but has since cut back as the cost of animals, travel, entry fees, stall space and even decorations have become a hindrance. It costs up to $200 to shoe an animal, Fred Gilbert said, while travel brings the risk of injury to his increasingly costly ponies.
The family will still travel to Minnesota, Omaha and various stops in Manitoba this year, but they now limit their trips to three-day fairs or longer, hoping to get more bang for their buck. This year, they will add Des Moines, Iowa, to their list of stops.
Despite becoming international horse show travellers, however, their season starts in their hometown every year in the dying days of March.
“I guess the main reason we do it is we love the people,” Fred Gilbert said. “This is our horse show family. Basically, whether it be the draft horses or whatever, we all kind of travel the same circuits.”
The Royal Manitoba Winter Fair ran March 27 to April 1, 2017.
