Jay Jensen is ride captain of Central Wyoming, my group’s 140-mile segment. He is also the owner of the infamous Blue, but I don’t hold it against him. Just shy of 60, he looks like he could grace the cover of a dime-store cowboy novel. His face is worn like a leather saddle, and he walks with the swagger of a town sheriff. The ring tone of his cell phone is a horse’s neigh, and the arm of his red shirt is emblazoned with the expression “cowboy up.” He once even drove a limousine for John Wayne when Wayne was filming a movie in Wyoming. This is Jensen’s 13th year to participate in the ride and his eighth year as a ride captain, which means he decides who rides when and where over the course of what turns out to be a 16-hour day. It’s a job he relishes.

“This is just awesome,” says Jensen, who works as a UPS driver. “I didn’t like history when I was in school. Now I can’t get enough of it.”
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THERE ARE ROUGHLY 20 OF US CONVEYING the mail from Jeffrey City to Casper, and our careers span the spectrum: teachers, accountants, truck drivers, businesspeople and hairstylists. While one person is riding, the others follow in a caravan of horse trailers, trucks and even a motor home, until it’s time to switch the mail pouch. We were supposed to hit the trail at 5:30 a.m., but the group before us was waylaid by a washed-out road and arrived four hours late after riding 40 miles straight. The onus is on us to make up lost time.

One of the first to hit the saddle is Paula Hess, a 59-year-old custodian at a Casper grade school. She joined the association in 1990, the first year it allowed women to participate in the ride — a necessary historical revision, as that year’s ride didn’t draw enough men in order to complete the trip. Today, half the riders are women.

An accomplished horsewoman, Hess has ridden the trail for 21 years. It’s a wonder she ever got back in the saddle after the first time, when her horse got spooked and dragged Hess on her belly across a swath of dust. “My pants were full of dirt, and I had blood running all down my face,” says Hess, who still bears a scar on her forehead from the ordeal. “They said, ‘Let’s kick someone else up on the horse to finish the ride.’ And I said, ‘Nope, I’m going to finish this.’ ” Exercising true cowgirl grit, she rode valiantly to the next stop: Wyoming’s Independence Rock, where settlers on the Oregon and California trails carved their names into the hard granite.

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She’s hardly the only rider to face peril while traversing parts of the original trail, where the grooves of wagon wheels are still visible in the hard dirt. A week before my turn behind the reins, a rider in Utah had broken her ankle when she fell from her horse. Her mishap is on my mind the next time I’m called to ride, about 20 miles west of Casper on the Oregon Trail.

This time, Jensen saddles Whisper, an 8-year-old Appaloosa with brown and white spots. I stroke her coat and tell her that she’s the most beautiful horse I’ve ever seen in the hope that she’ll be gentle with me.

Soon after, a rider draws his horse to my side. The mail pouch is quickly transferred to Whisper, and once again I hit the prairie, my rear slapping the saddle like a loose screen door in a windstorm.

Whisper wants to run, and I can feel her impatience. Her sinewy muscles quiver as I pull on the reins.

“Trot, Whisper,” I beg. “Come on, trot.”

But, just like my teenage sons, she ignores me and begins gathering speed. We are locked in a war of wills, and Whisper wins — rearing on two legs in protest at my repeated attempts to slow her gait. For a moment, no one says a word. Then Jensen gets out of the cab of his trailer carrying a length of rope.

“Here’s what we’re going to do,” he says. “I’m going to tie Whisper to Blue.” My old nemesis is now ­being ridden by Mike Achacoso, a former show-jumping champion in Louisiana who is now a vice president of Sinclair Oil Corporation. “I don’t think you should have no more problems,” Jensen says, attaching the rope to the horses’ halters.