It was 8 on a misty morning, and I was holding reins and a whip, looking between a set of pricked bay ears. I was poised and waiting for the sound of the start bell—and I was definitely wondering how I got there and why the heck I was wearing a dress.

Even with Cairo retired and pregnant, I had nonetheless started the summer planning some sort of show season. But instead of competing, I found myself checking scores online and following along wistfully on Instagram. Then one of my longest and best friends, Linda Fraunhofer, called and said, “Why don’t you come to Wisconsin and show my pony with me?”

The pony in question is named Bill. He’s 23 years old, of unknown lineage and probably about 11 hands on his hooftips. Of course I wanted to show the pony with Linda. 

Linda and I met 20 years ago when we were both riding hunters in Wisconsin. I moved to Oregon and became an eventer; she moved to Chicago and got into pleasure driving, but distance and changing disciplines doesn’t deter horse friends. Linda’s show season didn’t go to plan either, with one of her imported Shetlands still in training to drive and the other having some issues with his shoulder. 

But there was Bill, who thanks to Linda’s mom was in good driving shape and ready to go, and there was the Villa Louis Carriage Classic, in Prairie du Chien, Wisconsin—Linda’s favorite show and one of the largest pleasure driving show in the U.S., with 135 competitors this year.

There was also the very small detail that I didn’t actually know how to drive a horse. 

To be fair, I had actually driven a cart before. Twice in fact. Eight years ago, Linda entered me in a schooling show and taught me how to drive Bill really quick on her front lawn the night before. She was 7 months pregnant and able to drive on smooth ground, but the bumpy cross-country course was too much, so I took the reins and put in a fairly respectable round to finish fourth. Out of five. 

I never want to be one of those equestrians who looks down on other disciplines. I loved hunter/jumpers while I was actively competing in them, eventing now has my heart, and I figured driving would be fun. 

So once it was clear that the plan was underway to compete Bill at Villa Louis, I decided to set myself up for some sort of success by asking a fellow boarder at my barn, Wendy Andrews, if she could give me a couple driving lessons on her lovely Welsh pony, “Belle” (Pruitt’s Dainty Belle). Wendy generously offered to fit me in after she finished her last show of the season and before I left town. 

We got in two driving lessons as well as a basic review of safety and how to hitch the cart, as well as an introduction to a new language of traces, breeching and blinkers and such. And thank goodness we did, because Linda and I had planned a driving lesson before we loaded Bill for Prairie du Chien, but a rainy morning and wet lawn put a damper on that idea. 

The Villa Louis show mainly runs Saturday and Sunday, but on Friday it offered a Carriage Association of America event called a Sporting Day of Traditional Driving, as well as the chance for some competitors with multiple entries to get their drives in early for Gambler’s Choice and timed obstacles (a.k.a. cones).

The show takes place on the gorgeous Villa Louis Historic Site on the Mississippi River. Between that, the parade of carriages and drivers for the traditional driving event, who looked like extras in a scene from “Downton Abbey,” and the elaborate picnic class, at times I felt like I had wandered into some sort of cosplay gathering as costumed equestrians swept by me. 

Bill is a patient pony, but he had kind of hoped his show career was over, and he had absolutely no interest in trotting around for 20 minutes at a time in ring classes, so we only entered the timed obstacles (a.k.a. cones) and Gambler’s Choice, with Linda driving in her small pony open classes Friday while I went Saturday in novice driver. This, Linda pointed out, meant she would get the pony out on course and introduce him to the obstacles before I jumped into Bill’s little Meadowbrook cart.

The evening before the show, Linda and her mom, Sue Schrage, took me over to the cones course and we walked it. I’m used to walking courses and muttering things to myself like, “Five strides from the red vertical to the oxer,” but this was a sea of orange cones with balls on top (12 sets to be exact) and the only familiar thing was the fact, like eventing, they were marked with red on the right and white on the left. Also, if Bill were to canter more than four strides, I would incur a 5 second penalty, so strides weren’t even a thing. Instead Sue was explaining how to take the length of the vehicle and where I was sitting into account when I made my turns. 

Then we walked Gambler’s Choice and discussed strategy like how to whack a small whiskey bottle off a post with my whip (15 points a bottle) while driving, and whether it was better to try to hurtle Bill’s small, chunky and slightly unwilling body around barrels (40 points) or do the “strip tease” of colored cloths hanging from a line again (20 points). It was agreed that I definitely needed to drive over the traffic cones with balls on top to knock the cones out of a painted circle (50 points each). This seemed particularly hard given part of the point of the earlier cones class was not knocking the balls off the cones you were driving through! 

Earlier, I said I was wearing a dress, and Linda and Sue probably shook their heads as they read those words. It is, in fact, an apron, and men and women wrap it over their clothes for driving—historically to keep the dirt and mud your horse would kick up off your outfit. Since we weren’t competing in turnout or any of the ring classes in our division, and so not wearing fancy hats and outfits to complement even fancier carts (two wheels) and carriages (four wheels), Linda loaned me aprons to wear with matching shirts, and we wore helmets instead of the elegant hats. We also wore brown gloves as the reins in driving are traditionally brown.

Linda spun Bill through the timed obstacles course, managing a turn so tight between 8 and 9 that it was basically a turn on the haunches, except with a cart. Later in the day she turned it up a notch for Gambler’s Choice, whacking bottles with abandon and even finishing on the barrels, despite Bill’s short legs and laid back nature — ending up with a score of 355 points. Because the rest of her group would go Sunday, we didn’t know where she was in the standings. 

We spent the rest of the day watching classes like “antique vehicle turnout” and “drive and ride,” while I peppered Sue and Linda with questions about how the classes were judged. I was stunned by the two Shires being driven tandem (one in front of the other) in front of a driver sitting 7 feet high, and by a hitch of three horses called a unicorn with two pulling and one in front. 

I loved seeing women in their 80s happily competing alongside incredibly talented younger drivers. And I was fascinated by the overlaps between driving and riding: Working classes basically being judged almost like hunters on the suitability of the horse to a pleasant drive and reinsmanship, which is judged on the driver, and—my favorite as an eventer—the self-explanatory cross-country pace. However, I have never in my life encountered actual skunk scent to go with a skunk-decorated cross-country obstacle. I also have no idea if longtime show manager Mike Rider was kidding when he said he tried to fill the water crossing with foam. (He failed, but none of the drivers seemed to think he was kidding.) 

At the end of the day, we pulled a somewhat reluctant Bill out of his stall for a third time and popped me in the cart for a quick practice session. I also persuaded Linda to run to the liquor store and get some travel bottles of Jack Daniels for me to work on whacking. Under Sue and Linda’s watchful eyes I kept my back straight and hands up, with my whip at 10 o’clock and we trip-trotted around. 

I couldn’t be nervous, because beyond remembering my course and hoping Bill wouldn’t canter, I didn’t even know what to be nervous about. I’d barely driven a pony, let alone competed in driving. As it turns out, worrying about Bill cantering was a nonissue. I was grateful for the blinkers on Bill’s bridle, because they kept me from seeing what I was pretty sure was a judgmental little pony rolling his eyes at me. 

Bill did not canter. Bill babysat me. We trotted through those cones and did lovely turns and had a clean round. People think because the mare I evented is a hot horse, I am a hot rider, but the opposite is true. Cairo and I did well because I was the quiet yin to her wild yang. And apparently my tendency to quietness extends to driving ponies. I wouldn’t have been surprised if Bill had yawned.

We had a very slow, clean round. Very slow—I was a good 9 seconds behind the horse and driver that were in fifth and I finished just out of the ribbons.  I was thrilled; my goal was to be safe and not look stupid. Achievement unlocked. 

However, I am a wee bit competitive, so after putting Bill away, I studied the people in the other divisions on course for Gambler’s Choice and plotted strategy until it was time to harness up again. Putting the harness on is in itself is interesting: Someone needs to “head” the pony while you are getting in the cart, and you can be eliminated if your horse is not wearing a bridle with the reins attached to the bit whenever fully put to or being taken out of a vehicle. One competitor was told by a judge he lost the class because a trace wasn’t run through the right strap. Safety, as it should be in all horse sports, is huge in driving.

We headed over the warm-up for Gambler’s Choice, and Sue schooled me. After watching Bill and I poke around, she pointed out I was basically just annoying him with the whip, and he wasn’t listening. I admitted that I was perhaps intimidated by the large carts, carriages and horses of the others in novice driver. 

“You’ve done hunter warm-ups,” Sue pointed out. Touché. 

I gave Bill a smart tap—basically the equivalent of finally putting my leg on—and headed for the start. Bill broke out his game face. 

It was a blast. We zipped over a red carpet and managed to both be fast and turn nicely through the Y-obstacle and the U-turn, and Bill plowed over the cones and balls with enthusiasm. We did skip the barrels but negotiated everything else handily before the buzzer rang. OK, I did flail at the whiskey bottles, knocking over only one out of three on both tries. It’s really hard to knock over a small bottle of whiskey with a long whip while driving a pony! 

We put Bill away with much praise and some low-sugar, low-carb treats, and were soon joined by Sue and Linda’s cousin, who had stayed to watch the rest of Gambler’s Choice. They informed me, to my shock, that I was in the lead. Bill was the only small pony in the novice driver division, but apparently his short little legs were speedy that day. He might cover less ground than the Hackneys and Clydesdales in our group, but his small stature and the two-wheeled cart meant we could do faster turns. 

As the results started to come in, I was happy—and unsurprised—to hear that Linda had won Gambler’s Choice in small pony open. She also finished third in cones. And then there was me, an eventer who, despite years of training and trying, never finished better than second to last in dressage while competing at preliminary. 

Bill and I brought home the blue ribbon and silver cup for first place in our Gambler’s Choice class at one of the biggest pleasure driving shows in the country. I guess I had a show season after all.

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Camilla Mortensen is an amateur eventer from Eugene, Oregon, who started blogging for the Chronicle when she made the trek to compete in the novice three-day at Rebecca Farm in Montana. She works as a newspaper editor by day.