Seeing the Fryeburg Fair changed Steven Wilson’s life
by Chris Lomon
It was unlike anything Steven Wilson had ever seen.
Everywhere he looked, the young man who hails from just outside Liverpool, England, found himself in awe.
Fryeburg Fair — Maine’s largest agricultural fair — offered a sensory overload for the teenage Wilson, with its exhibit halls, museum, livestock shows, and harness racing.
“I ended up coming to Maine to see the Fryeburg Fair and visit my cousin Charlene [standardbred trainer, Cushing],” Wilson said. “I had a blast. So, the following summer, I came back to do the fair circuit horse racing with Charlene and Mike [trainer, driver and director with Maine Harness Horsemen’s Association, Cushing]. And here I am, 17 years later.”
These days, Wilson is firmly entrenched in Maine’s harness racing scene – as a driver, trainer, second trainer, and farrier.
Not that he saw any of it coming.
“It’s different, for sure,” Wilson said. “But I absolutely love it.”
Working full-time with the Cushings since 2008, Wilson launched the driving side of his career seven years ago.
It was Ideal Bid, a now-retired son of American Ideal—Highest Bid, who gave Wilson his first driving win.
The victory came at Windsor, a half-mile oval in the Maine city of the same name, on Sept. 2, 2018.
Leaving from post 4, Wilson and Ideal Bid sat second through an opening panel in :28. At the half-mile pole, they were 1¾ lengths in front, their advantage widening to two lengths through three-quarters in 1:27.2.
Ideal Bid crossed the line — after a final quarter in :30 — ٢¼ lengths ahead of his nearest rival, stopping the clock in ١:٥٧.٢.
“It was pretty epic – I had been driving at a handful of fairs leading up to that race,” Wilson said. “I had a bunch of seconds and thirds and had just come up a little bit short.
“The horse was known for racing on the front and on that day, he was a little hot. When you know you’ve got a stone-cold frontrunner, being able to manage him, putting him in a hole, watching him swell up and then take off — and you have just started driving — it was an awesome feeling.”
Wilson was, to say the least, euphoric in the final few steps to the wire.
“Down the stretch, I remember tucking my whip and then I thought, ‘I am going to be embarrassed if someone comes and gets me late,’” he said. “But fortunately, that didn’t come close to happening. It was a sigh of relief to pull that first one off.”
Piloting the practiced pacer would be twice as nice for Wilson, who teamed with the bargain-priced ($2,000 purchase at the 2010 Harrisburg Yearling Sale) gelding to win 16 days later at Farmington.
By year’s end, Wilson made 14 total trips to the winner’s circle, accompanied by just north of $88,000 in purse earnings.
Most importantly, he learned valuable lessons about the horseman craft.
“I appreciated the work you have to put in even more than I did,” Wilson said. “Working as second trainer for Mike and Charlene for a lot of years – there is so much that goes into the horses, especially the babies. There is always that big excitement when you work with them and help get them to the races.
“When you start driving, you can see why everyone in a barn gets so excited about seeing their horses make it to the races. You also appreciate the older horses, who go out there and give their all over a lot of miles.”
Just like Wilson has.
Aside from his duties as second trainer for the Cushings, along with his own driving and training roles, Wilson does farrier work as well.
“I work for Mike and Charlene full time,” he said. “The past few years I have had a horse of my own here and there to train — I keep my horse in the same barn — and then I do the shoeing full time. I shoe all Mike and Charlene’s horses — they have 22 in the barn right now — and I shoe about 25 horses outside of their barn. I am fully involved in the business.”
Something that does present its challenges.
“I am sure one day, with being so busy, it will catch up to me at some point,” Wilson said with a laugh. “I truly enjoy everything I do, but I think a time will come when I might have to give something up.”
That could be a role he is quite adept at, one that produced a career-best year for him in 2024.
“I love driving,” Wilson said. “The adrenaline, the feeling, the connection to the horses – it is wonderful on every level. I might have to reconsider if I want to keep doing it down the road, but I have been very fortunate to drive some wonderful horses and had success.”
Emmajean Jellybean, a daughter of Mister Anson—Quote Of The Week, is one of those horses Wilson speaks of.
The pair have teamed up for multiple winner’s circle trips, including a half-length score this May at Plainridge.
A lifetime winner of 22 races and closing in on the $300,000 mark in purse earnings, the 7-year-old trotting mare has a personality to match her competitive spirit.
“She will pin her ears back and give you this look of, ‘Don’t mess with me,’” Wilson said. “Sometimes, the girls who work in the barn will tell me to come to see her because she’s being difficult. But she just isn’t that way with me. I’m her person and we both know it.”
Outside of the hectic pace that comes with the horse racing life, Wilson enjoys spending time on Maine lakes in the summer and snowmobiling on state trails during the winters.
“Being out on the water is always very calming and being on a snowmobile gives you that adrenaline like driving a horse – it’s always exciting to explore new paths,” he said.
Something he is certainly familiar with.
After all, it was a 3,000-mile trek and a state fair first held in March 1851 that brought him across the Atlantic Ocean and put him on the road to horse racing.
“It’s a pretty unique story, I suppose,” said Wilson. “But when I saw those horses and the atmosphere at Fryeburg Fair, it just stuck with me. I knew I would be back and that’s exactly what happened – I’m very grateful how it all worked out.”