How (and Why) I Learned to Ride

When I was young (growing up in Stockbridge), the closest I came to riding a horse was being led around a circle during the pony rides at the Church Fair.

I’ve always (at least as long as I can remember) been an inveterate gambler and card player. As a youth, I loved playing board games and card games with my family and friends. As I grew into my teenage years, I advanced from Monopoly, and began to gamble with penny-ante poker.

My Scoutmaster regaled me with tales of race-fixing at the Barrington Fair. I had for years enjoyed watching the horses run around that little track — it was so small that there was no portion of it that was straight — the horses were always going around a bend. When I was 14, I worked up the nerve to go to the $2 window with a bet. “How old are you?” the teller asked me. In those days before picture IDs, I figured I could fake it, so I said “Eighteen,” thinking that was the legal age for betting. “Go away,” the teller motioned me off with the back of his hand. “Why?” I wanted to know. “You have to be twenty-one,” he told me. So I went down the line a few windows and tried again. That teller never asked.

For the next twenty-odd years, I bet on the ponies from time to time. As a college student in Springfield, on my lunch hour at the Milton Bradley warehouse, I sometimes took the bus down State Street to visit my bookie. He had a glass repair shop, and told me that he was friends with many of the local cops. Some of them knew about his side business, but others didn’t. If I came in and there was a policeman there, I was to ask if my mirror was ready. If he said, “You’ll have to come back tomorrow,” that meant he was unable to take a bet at that time.

Later, when I was living and working in the Hartford area, in the summer I would often drive up to The Spa (the Saratoga Race Course) to watch the ponies run. (I still go there every year.)

But I had never been on the back of an actual horse.

Fate intervened. I was working at Morgan Stanley in Manhattan when I met a beautiful young woman who would change the course of my life. Nadia was a client. We developed a deep friendship, and shared stories with each other. She told me about her time growing up in Switzerland, when she and a friend had taken their horses out into the countryside to ride through the meadows in the Alps. “I want to do that with you,” I told her.

It wasn’t clear how that was going to happen, since I did not know how to ride, and I had a feeling my wife would not approve. Still, the dream had been planted in my mind.

A few months later, I had a chance to learn.

My brother Bruce was going through a rough patch. He had suffered a stroke, and was out of work. One day, he was not feeling well and asked me if I would take his two children to their horseback riding lesson. I was happy to give them a lift, and to pay their fee (ten dollars each). I sat outside the fenced training area. They were perched on small horses, and went around and around in an endless circle. It was quite boring, but I offered to take them again the next week.

When we arrived for the next lesson, I told the instructor of my boredom. “It doesn’t look too difficult,” I told her, “I wonder if I could join in, instead of just watching them.”

“Sure.” she said, “I have a horse your size.” And so it began. As soon as I mounted the horse and did a couple of trips around the enclosure, my insides broke into a smile. “Why haven’t I been doing this all my life?” I wondered. I was forty-two years old.

One week, when we arrived for our lesson, it was starting to rain. “We’re going to have to move inside,” the teacher told us. So we led our horses into the indoor ring, and began doing clockwise circles on the outer edge of the enclosure. My horse was much larger, with a longer stride, than those being used by my niece and nephew. I would hold him in place and let the other two go on ahead so as to open a bit of a gap. When I started up again, I would soon catch up with them, and pause my horse again.

Not quite halfway through our hour lesson, Kim said to us, “Just keep doing what you’re doing — I’ll be right back,” and she headed for the exit. I knew she was going out for a cigarette break, and would be back in five or ten minutes. Meanwhile, I was finding my stop and go routine to be a bit annoying, so I devised a new scheme. When my horse caught up with the kids, I would leave the path and do a small clockwise circle, ending back on the outer circuit somewhat behind the others. This was much more satisfying because I got to ride continuously.

When Kim returned, she watched me do a couple of my loops, and then she held up her hand and told us to stop. She walked over to me and asked, “What are you doing?” I thought it was pretty obvious. “I’m just wasting a little time so that I am not always bumping up against the backside of Matthew’s horse,” I explained.

“Yes, I can see that,” she said, “but how did you learn to do those little circles?” I just decided to do it, I told her, and wondered if it was all right. She looked at me in amazement. “Sure,” she said, “it’s perfect. But it takes most people years to learn how to do that.”

And so it went. Another time, I arrived at Bruce’s house to discover that the kids had just come down with a fever and were in no condition to ride that day. Having traveled the forty minutes or so to get there, I decided to go another five and ask Kim if I could ride anyway. “Sure,” she said. “What I’ll do is put you in a lesson with two teenage girls who are just starting to learn how to jump. You can learn, too.”

For our first few turns around the paddock, we simply had the horses step over cavaletti (ground poles) to get a sense of the rhythm involved in jumping. Then Kim began raising them a few inches at a time until we had to do a small jump to get over the poles. “Okay, you’re ready for the real thing,” said Kim. She reminded us to keep our weight forward and to signal the horse with our legs when it was time to jump.

Kim set up a two-foot jump near the far end of the oval, giving us a clear approach. “Watch the girls do it a couple of times,” she told me, “because they have done this before. Then you can join in and take your turn.” When it was time for me to go, I imitated what the girls had done, and in that first moment of being fully airborne, I experienced a moment of joy like no other I had ever known.

After a couple more practice jumps, I knew that the only thing that would be more thrilling would be to go faster and higher. So on my next approach, I revved up my horse for a full charge. “Slow down!” yelled Kim, perhaps thinking the horse was out of my control. Too late! We flew so high we might as well have been jumping over the moon. The only similar experience for me came from floating down a mountain on skis. I’m guessing that both of those things activate the same pleasure center.

I took many more lessons, to refine my technique. Not every horse was a pleasure to ride, but from the very beginning, I was able to bond with most horses, so that it was impossible to tell which one of us was having more fun.

I experienced the joy of riding through the woods and meadows near where I live. Sometimes I would ride alone, but almost always I rode with one or more friends — often with my friend Amy. We would canter through fields of wildflowers in the Spring, or jump over fallen trees on paths through the forest. The horses loved going out into newly-fallen snow, sometimes so deep that it came up the bottom of their chest. We would race along old woods roads.

Horses evolved to run fast, probably to avoid predators, but they did it for fun, too. The first time I ever raced was quite soon after I had learned to ride. I was riding along a dirt road with Amy and her friend Cherie. Amy stopped and pointed to a large maple tree at the top of a pasture that was next to the road. “We usually race up the that tree,” she told me. “You don’t have to race, but your horse will want to keep up.”

“Does he know how to canter?” Cherie asked.

“I guess he’ll figure it out,” said Amy, and off she went.

So that’s how I learned to canter. It was called “hanging on for dear life.”

Once I had learned the thrill of cantering, it was hard to hold me back. One time, after galloping off and leaving Amy in the dust, she had to ask me to slow down. “I don’t want my horse to think it’s okay to go that fast,” she said.

I had never forgotten the fantasy that had first motivated me to learn to ride. After several years of riding, I was ready to make that dream come true. In the intervening years, I had moved from New York to Boston, and I was no longer married.

Nadia found a place in the mountains that offered an opportunity for us to ride. As it turned out, the experience did not quite live up to my fantasy of a carefree ride through a flowered meadow. I was thrilled, nevertheless, to be able to finally ride with her.

A long train ride brought us to a picture-book Swiss town.

The small town had traditional Swiss architecture, including the local theater.

The barn that she had chosen sat at the edge of a pasture, with a dirt road leading out into a tree-lined pathway.

The path leading from the barn into the countryside.

We soon were making friends with the horses.

Then the trouble began. We were not to be permitted to take the horses out on our own. The woman who was to lead our trip sized me up and handed me the tack for one of the larger horses in the barn. I entered his stall, and he immediately let me know he was not pleased with the idea of going for a ride. As I tried to saddle him, he turned away from me and started kicking the back wall. Hard.

I was getting a little nervous, so I left the stall to tell the leader that perhaps another horse would be more suitable. “He’ll be fine,” she assured me, “he just doesn’t know you.” She came over and completed the job, and I led him out to join the other horses and riders. Once I had mounted my unfriendly horse, he became quite docile. So much so, in fact, that I was afraid he was going to fall asleep while walking.

Our group of a half dozen or so riders headed out walking toward the woods. And that’s all we would do. Walk. No trotting. Just walking. Back to my days at the church fair. Oh, well! This ride in the Alps was what I had always wanted to do, and I was doing it. I’m glad we made it happen. It was a dream come true, even if it did not match the dream I had dreamed. And ahead of me were many more years of joyful riding, all thanks to that long-ago inspiration.

When I got back to Boston, I wrote a note to Nadia.