Seasoned trail rider Ben Theyre and his mount, Thunder, ready for a ride. The duo had a shaky start, however. “My rocky start to trail riding on Thunder taught me that horseback riding isn’t easy,” says Ben today. “It’s a skill that needs to be learned. To succeed, it’s necessary to approach your mount with a healthy balance of humility and a desire to improve.”

There’s a first time in the saddle for every trail rider. Here’s my story.

Even though I came to know and appreciate horses during adulthood, I didn’t jump into riding right away. In fact, it took about two years to decide that riding was for me. When I finally climbed into the saddle, the experience taught me to overcome an instinctive fear of personal injury and one of the primary virtues we all need in trail riding, humility.

Being raised in the suburbs of Chicago, there was little opportunity for me to be around horses. With the exception of attending local parades, I really didn’t see a horse up close until I hit the magic age of 40. That’s when I met Vanessa and all her horses.

Our relationship began by chance in 1992, during a trail ride that benefited our local Kiwanis Club. At the time, I was a single marketing executive in an environmental engineering firm. Vanessa owned a farm and managed the trail ride. The friendship grew, and I started to hang around her farm. I helped out in the barns, but I didn’t feel comfortable even handling the horses.

Then, one day, I was handed the end of a lead rope and handling horses became part of my skill set. There would be many opportunities to practice my new skills, as Vanessa and her horses were always entering distance-riding competitions, particularly endurance races and competitive trail rides.

Before the end of the summer, I was going to her competitions — not as a horseman but as crew, well — a gofer. Despite my lowly position, the events were fun and exciting. I didn’t mind. Vanessa usually ran in the front of the pack with her best horse, Thunder. He was a handful at times, but she kept him under control, and won several trophies and many ribbons. Watching the horses and riders in competition was entertaining, and besides, managing a cooler full of ice-cold beer was considered an important part of my job.

The exposure to these events over two summers had an effect on my perspective of horses. I could see that trail riding was a great form of entertainment, but this enthusiasm was tempered by several mishaps I observed. Seeing people and horses get hurt kept my aversion to riding very real in my mind. I had no doubt that pure, unadulterated fear kept me content in my official capacity as "bucket-boy."

But all along, there was this little voice inside of me that had sparked a desire to get up on a horse and experience the trail with Vanessa and the others. The desire to ride a horse began to outweigh my fear of injury. In order to compensate for my instinctive fear, I adopted an attitude of confidence. I began to visualize myself as a self-assured trail rider who rode high in the saddle.

After watching Vanessa compete and work with horses for several months, I started telling myself, "I can ride a horse; heck, Vanessa and her friends do hundred-mile rides, how tough can it be; there must be nothing to it." I thought it’d be easy. I’d just get on and ride. Poised to begin this new dimension in my horse experiences, I made it my 1994 New Year’s resolution to begin riding in the spring.

To psych myself up for the inevitable event, I told Vanessa about my resolution. It was on a cold, sunny day in January. We were sitting at her desk in the farm office the day after a heavy snowfall. I spewed confidence as I announced that she could plan on having me ride with her in the spring.

To my surprise, Vanessa got up, put on her coat and walked out the door. "Let’s go now," she said. "There’s no time like the present." I followed her as she walked to the barn. She handed me a lead rope, and we went out to the paddock to retrieve the steeds. Back in the barn, she began to tack up Beene and Thunder. They both stood like statues. I handed her a bridle.

"You can ride Thunder," Vanessa said. "He’s a pussycat." I rid my mind of the image of Thunder during competitions, unwilling to let Vanessa mount him, galloping with his head high, and refusing to relax in the holds. But I wasn’t going to let this unexpected commencement of my riding career unnerve me. While she flopped and tightened the equipment, I mustered up all my nerve and desire to succeed.

I guess I may’ve overdone it.

The horse was held as I placed my foot in the stirrup, swung up, and settled into Thunder’s saddle. I was there! We followed Vanessa and Beene down the driveway and into a field. Wow! I was riding. Then I looked down, and took my eyes off Vanessa and Beene. I noticed that the snow drifts from the storm the night before were easily three to four feet deep. Mistake! When Vanessa bumped Beene up into trot in the deep powder, Thunder instinctively followed.

I lost balance, then concentration, and Thunder knew it. The good feeling of security and confidence quickly changed to fear when suddenly Thunder stopped and started hopping. He wanted the greenhorn off his back. In an instant, I was neck deep in a snowdrift, a bit embarrassed but laughing.

Vanessa stopped and turned around to find out what the commotion was all about. The confident macho man got dumped in the drift. Instinctively, I got up, brushed the snow off, climbed back on Thunder, and off we went, a bit more focused.

The remainder of the ride was incident-free. We ventured into the Bristol Hills for a memorable afternoon of winter trail riding. That evening, we sat in front of the woodstove with a hot cup of tea, thawing our toes and reminiscing about the day.

I swallowed my pride and confessed that

I was a bit overconfident. She laughed and figured Thunder just wanted to tell me to pay attention and get centered if I was going to be on his back.

In either case, I ate a big piece of humble pie that day, but for a good cause. My rocky start to trail riding on Thunder taught me that horseback riding isn’t easy. It’s a skill that needs to be learned. To succeed, it’s necessary to approach your mount with a healthy balance of humility and desire to improve.

Follow this advice and, like Thunder and me, you and your horse will be happy and safe riding partners, enjoying your favorite trails with friends.

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