(Photo: :copyright: Nate Bressler)

A Wild Ride on the Pony Express


If you want to know what it was like to travel this legendary trail, there’s only one way: get on a horse and follow all 2,000 miles of it. That’s what writer Will Grant did, retracing the route from Missouri to California over four and half months. He cooked his own meals and never knew where he’d end up camping on a given night. It was a grueling feat of endurance and logistical fortitude, but it gave him exactly what he was after—the chance to truly understand the people, land, and history of the American West.

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Podcast Transcript

Editor’s Note: Transcriptions of episodes of the Outside Podcast are created with a mix of speech recognition software and human transcribers, and may contain some grammatical errors or slight deviations from the audio.

Michael Roberts: From Outside Magazine, this is the Outside Podcast. 

Years ago, when I was living in New York City, I had this fantasy of riding a horse right down Park Avenue. I imagined an enormous snowstorm that shut down traffic in Manhattan. And somehow, I get a hold of a horse, a big one, and I go galloping down that urban canyon. And then, I pull up outside a bar downtown and go in for a whiskey.

Kind of silly, I know. I blame my childhood afternoon of watching reruns of Bonanza.

I'm Michael Roberts and over my years at Outside, I've worked on a number of stories about people who had much bolder fantasies than mine, and actually saw them through. People who sailed or paddled across oceans, or biked or walked or skied across continents, and, yes, that particular breed of adventurer who chooses to travel by horseback.

Which brings us to today's episode, featuring an especially intrepid horseman, who got it in his head to ride one of the country's most iconic trails. Producer Paddy O'Connell brings us a story that explores the enduring excitement that we feel when we head into the West.

Paddy O’Connell: How many showers did it take to not smell like chicken fry and badger once you returned home?

Will Grant: I had to shave the beard. You know, I couldn't get this, this musk of horse sweat off of me. I was like, breathing and seething horse sweat. It took a little while to wash the dust off.

Paddy: This is writer Will Grant describing the, ahem, specific trail bouquet one is adorned with while traveling with two horses. It's not that his ponies, Chicken Fry and Badger, are extra horsey-smelling though. Will spent some four and half months and 2000 miles with them, retracing the Pony Express route from Missouri to California for his debut book, The Last Ride Of The Pony Express.

And if you're wondering what kind of whackadoo human would bite off such a grueling and stinky adventure, you have to understand that Will Grant loves horses. Like, really loves them.

Will: When I am lying in my bed trying to fall asleep at night, I think about horses.

Paddy: Really?

Will: Not going to lie, I really do. You know, I don't know what it is about those animals that has affected me so strongly over the years, but there's something about them that I just can't get enough.

Paddy: Has it been like that forever?

Will: Forever. First picture of me on a horse, I'm two years old in 1981.

Paddy: Will grew up outside of Denver, Colorado, but most of his childhood memories center around time at his family's ranch in Steamboat Springs. He says that is where he was first exposed to and fell in love with horses and cowboying.

Will: I remember a horse named Echo in Steamboat. That's probably the first flesh and blood horse in my memory.

But I had a plastic horse when I was a kid that you could rock back and forth and it would scoot across the floor, and it was called Bucky, the Wonder Horse.

And I remember Bucky. And I, I put the horse on the coffee table and rode it off the coffee table. And then I took it to the top of the stairs and rode it down the stairs. I'm not sure how, I didn't get hurt doing that.

Paddy: What started with Echo and Bucky the wonder horse continued through college. After graduation, Will cowboyed and trained horses in Colorado, Wyoming, and Texas. He then switched careers to journalism in 2008, but his love for all things cowboy came with. He raced horses across Mongolia, looked for gold in Arizona, and rode 400 miles across Wyoming for stories for Outside. Simply put, Will is enthralled by horsemanship.

And in his estimation the greatest display of American horsemanship to ever hit the West was a hoofed precursor to the United States Postal Service that was set up in 1860.

Will: The Pony Express was set up as a 10 day mail service to span the West. And it was a fast horse relay, which means that riders would travel at speed and change horses out at weigh stations. They would ride the horse for 15 or 20 miles and get on a fresh horse. 

And so this required an extensive infrastructure of stations between the Missouri River and California. So that was about 190 way stations. And it Only lasted for 18 months because it was prohibitively expensive. It just cost too much to run the mail that distance. So the Pony Express was like this last glimpse of the West pre-civil War.

It didn't really foster any settlements. It didn't really bring about any change. A lot of people recognized the name, but all it did was carry letters.

Paddy: You might be wondering why a thing that lasted less than two years and didn't have much of a historical impact still captivates people today. Will has a few theories. The first is, well, good marketing: "Pony Express" is a catchy slogan. Plus, like any memorable brand, it has a pretty frickin' sweet logo.

Will: All the iconography of the Pony Express shows a galloping horse and cowboys. Like you think of the Transcontinental Railroad. That's not that cool.

Paddy: Yeah.

Will: It was certainly a, a tangible expression of the expansion of the United States in the 19th century, but really it's not that cool. I think that's what the Pony Express  carries a little bit, like this sense of adventure.

Paddy: And in Will's opinion, unlike many other parts of the history of the West, the Pony Express is not closely linked to the heartbreak of America's murderous expansion in the mid 1800s.

Will: The century of us expansion was in so many ways difficult, you know, as any sort of imperialistic expansion is gonna be. It has this very ugly price.

And yet through it we have this romantic perception of it. 

You know, there is this paradox that's very difficult to square. And so let us not be remiss about recognizing that. 

But I think the frontier was a fundamental part of making the American character. The West certainly informs our sense of identity, this idea of independence and one's resilience and the ability to endure hardship and a certain amount of freedom has certainly informed the national character.

And so the Pony Express. It is sort of a romantic notion of the West. It was nothing more than a mail service and it was young men running horses. This is pretty easy to wrap your head around. It's like good, clean fun in the West. This is like acceptable. It's palatable.

Paddy: Will first had the idea to retrace the Pony Express route in the spring of 2018 and within days he was off. 

Just kidding. It took him a year of planning. 

Before he ever made the first clops from the Missouri River toward Sacramento, Will had many pounds of logistics to figure out. First, he needed to secure two good horses. They would take turns carrying Will in his saddle, and following behind as a packhorse, loaded with gear and led by a rope that Will held in his hand.

Will: Badger is my bay horse. A bay horse is a brown horse with a black mane and tail. And Badger is like riding a Ferrari. His motor idols at a very high RPM. When you get on this horse, it's like sitting on a racehorse. So I, I could feel miles in him. I knew he had the motor for it. 

Chicken Fry, on the other hand, is like the most intelligent horse I've ever been around. He's like the Buddha. He handles adversity with such a level head.

And Badger, a more fractious horse. He gets scared easier. And Chicken Fry does not scare easily. And so Badger really relied on Chicken Fry as the leader. They got so tight. The bond between them was amazing. 

The relationship I developed with Chicken Fry and Badger over the course of that journey is some pretty unique territory. You know, this day in and day out with these two animals every hour of every day. This, uh, the water runs pretty deep.

Paddy: Finding horses that you trust and can get along with is one thing. But figuring out where in tarnation you're going to sleep with a few thousand pounds worth of hungry, thirsty animals is a whole different beast of a problem.

Will: If you're backpacking you can sleep anywhere. You can sleep under a bridge. 

But if you're traveling with two horses, you need like 80 gallons of water and a lot of fresh grass or hay.

Organizing the campsites on private land was the biggest job of the whole trip. I made a list of potential campsites every 25 miles for the entire trail. And I was looking at a hundred camps. I was like, this is absolutely ridiculous to even try to plan out this. The only thing I can plan out is the first two weeks, because there's no way to tell how far you're actually gonna be able to travel on any given day.

And after that, the logistics was an unending chore. It was so difficult. It was, it involved so many cold calls. Say, ‘Hey, my name's Will Grant, I'm passing through with two horses.’ And I would always try to name drop, be like, so I'm just coming from, you know, Kearney State Park. And then I was with Joe Jeffrey, and I was wondering if I might be able to sleep in your yard.

Paddy: Oh, like as, as like a ploy of like, ‘Hey, listen man, like Joe just helped me out and Joe was great. Could you be as great as Joe?’

Will: Yes.

Paddy: Nice. Smart move.

Will: Really, my motivation for doing that was like, if you are wondering if I'm an okay dude, call Joe. And it basically means that like your reputation moves ahead of you.

Paddy: On May 5, 2019, Will , Chicken Fry, and Badger finally set out on the Pony Express route. Will was one-part ecstatic, and nine parts relieved.

Will: To get started was the best thing to happen in a year. Basically, for the prior two weeks leading up to the trip. I couldn't eat, I was so nervous about everything. I was waking up at like five in the morning, couldn't go back to sleep.

I figured if something's gonna go wrong, let's just get this over with, you know?

Paddy: Yeah.

Will: Like obviously we're gonna run into trouble at some point. You know, I'm gonna have some kind of accident and, and there's nothing you can do about that. So let's just get started. Day one was a huge relief. And then I could start eating again. You know, then I was starving. 

Paddy: The core of Will's excitement wasn't all that different from what people might have felt 150 years ago when they saddled up and headed West.

Will: There is something about going toward California that has like an ideological component to it.

When I was first planning this, I considered riding from California to Missouri for the number one reason that the prevailing wind is out of the west, so I thought it would be way more enjoyable to just coast down wind for five months than to be into the wind. But the problem with going downwind is that we're going east. And the only reason anybody ever went east was to bail out and go home.

So I had to ride west. And there's this notion of crossing the west. What does that mean?

Three men put together the Pony Express. One was a guy named Alexander Majors and he earned his salt out west by crossing the west at the age of 15. He came back a different man. 

 And I thought for myself, well surely there must be something to be learned. 

If this is the kind of process that induced some maturation or some learning, I want to know what that is.

I don't really want to read about that. I want to know it firsthand. And I'm here to tell you it's for real.

Paddy: Coming up after the break, what went wrong--and right--for Will and his horses out on the trail.


Paddy: When Will Grant - and his horses Chicken Fry and Badger - set out on the Pony Express Route in the spring of 2019, he was excited to head West like so many of his cowboy heroes. But that doesn't mean he wasn't nervous as hell. Perhaps unsurprisingly, Will says there is no end of possible things to go wrong on a 2000-mile horseback journey.

Will: Whenever you are around horses, the greatest danger is that you get kicked in the mouth and you're never the same. People die from freak accidents with horses all the time. Like they, they're a thousand pound animal and you gotta be careful. And you gotta be careful when you got two of them.

Paddy: Today, a lot of the Pony Express route is either near or on roadways, which meant Will had to worry about his horses getting spooked by cars.

Will: I mostly rode on county roads and stuff, and so that wasn't too difficult. The highways sucked, and I tried to stay away from the highways.

you think you have control of the pack horse, but you don't. If he wanted to jerk you off your horse and run the other way he could. And if he runs into traffic and gets hit by a semi truck, it's gonna be a bad deal.

Paddy: Then there was the constant threat of rattlesnakes, as well as worries about another creature that most of us would never think was a concern.

Will: Some people don't know that there are 80,000 wild horses in the west and that being around wild horses with domestic horses is not a very fun situation and it is a dangerous situation.

Paddy: And then, of course, there's weather.

Will: You can't be caught out in big storms with a pack horse and a saddle horse because the storms are too intense.

One day, it was freezing cold. The wind was blowing like 20 miles an hour. The semi trucks are flying past me. There's these clouds of water vapor. So I'm soaking wet wearing jeans, leather boots, always a lot of fun and Badger has a sore back.

And Badger basically didn't wanna walk forward. And he threw himself down in the grass wearing the pack saddle on the side of the highway.

Like when a horse throws himself down and acts like he doesn't wanna walk forward, you got a problem on your hands.

Something is wrong here. I figured that somebody driving down the highway was gonna call the Humane Society or report me. 

Paddy: Oh my God.

But surely, when Will was mounted up and the skies were clear and the snakes were asleep, he was able to let go of his fears and enjoy the journey, right? 


Will: Just riding, there were dangers. I worried about the horses basically stepping on something that would permanently injure them. 

You know, if a horse steps in a hole, it can damage its leg in such a way that you can never ride it again. Or it has to be put down.

Let me tell you, the borrow ditches in Nebraska are full of beer bottles and beer cans. I'd hear this pop and they were never lame from it, but I sure worried about it.

Paddy: When Will would finish a day's ride, he'd find himself at a campground or a ranch or farm where he'd made arrangements to sleep. And not all camp spots are made equal.

Will: When there are ticks crawling all over you, throughout your clothing. They're all over the horses. They're inside the horses' ears. This is a bad camp.

I also camped at a few places that were absolutely filthy.

I was at one barn in Nebraska where I thought it was almost unsafe to sleep inside because of the vermin. I mean it was skunks, raccoons, they were all in there. The barn had had chickens in it previously. It was absolutely filthy. There was no place on this farm that was clean for me to sleep in. So I slept outside. And it was unfortunate cuz it rained like hell. I tented up that night.

It was a one person ultralight tent, and my hat wouldn't even fit inside the tent.

Paddy: Where you're like, if I take a deep breath, I'm gonna like suck in this zipper.

Will: Exactly.

Paddy: At the onset of his journey, Will knew it was a given that an accident would happen. You just can't spend that much time on a trip with so many variables and have nothing go wrong. And in the west desert of Utah, a five day’s ride from Salt Lake, it finally happened first thing in the morning, when Will was closing a wire gate.

Will: And Badger spooked and pulled my hand across the barbed wire. And opened up a cut at the base of my thumb and it was bleeding and the med kit was packed in the bottom of the panier on the pack horse already loaded and ready to go, it would've been uncomfortable to unload everything and dig out the med kit. I had a little pack of Kleenexes that had been in the saddlebags. And so I, I was able to get the bleeding stomped, but it bled a lot.

Paddy: With a large open wound and no real bandage, Will worried about infection. So he rode for the entire day with his left hand held out away from his dirty clothes and horse. For nine hours. 

Will: The muscle cramps were unbelievable, all through my shoulder and my bicep. And with the other hand, I had to control Badger and hold the lead rope to the pack horse. And so this was an exhausting day for me. And worrisome. So that was a hard day. 

Paddy: Reading The Last Ride of the Pony Express, it's impossible not to be amazed by all the things that Will endured to get through his 2000-mile adventure. When I asked him how he was able to manage it all, he said that being organized helps, but that the most important factor in maintaining unwavering optimism.

Will: If you travel for five months, I don't care what you do, you're gonna have hard days. And all you can do is just keep your chin up and try to remain optimistic that when things are not going well, It means that they're about to turn around.

If you have a bad camp, it means that the next night is almost certainly gonna be better. And if you have two bad nights in camp, then your third night has definitely gotta be better.

I realized that I had to remain optimistic and kept telling Chicken Fry and Badger, ‘trust me guys, it's going to get better.’

And I was like, we are going to California, you know. For, for the record we are going.

Paddy: Yeah.

Will: And so we, uh, better just suck up and deal with it.

Paddy: Ok, but it wasn't all about smiling in the face of pain and hardship. There were many moments that refilled Will's tin cup with optimism. And many of them were due to the characters he encountered along his journey.

Will: It was so refreshing to know that hospitality for a passing stranger still exists in the west. There were places that I didn't want to leave.

Paddy: Among the most memorable people that Will met was a rancher named Tom Damele at the Dry Creek Ranch in central Nevada. While splitting most of a jug of Carlo Rossi wine, Tom told Will a story about having to put down a bull with a broken leg. He was forced to shoot the bull 13 times.

To Will, Tom is a prime example of a character of the West: gruff and tough, but also warm and approachable.

Will: This guy was such a class act. He was a true man of the old West. Like, this is Mr. Johnny Cash incarnate right here. Dignified air. The way he carried himself, you knew it. He had a lot of natural charisma. And you knew it before he even said anything.

He found me camped in his yard and I was like, I won't be any trouble to you. I'm so sorry. You know, I just wanna stay one night. He's like, get in the truck. I was like, okay. And then he didn't really say anything for like, uh, five or ten minutes.

And then he looks over and he said, when I seen your tracks at the gate, I thought you were a beautiful woman come to visit me with two horses. 

I was like, this is a cool guy, you know?

Paddy: Sorry to disappoint you, sir. 

Will: Yeah, sorry, sorry to disappoint you.

This is what made the knights in camp so enjoyable. So I would ride out of this guy's place thinking like, wow, I'm so lucky that I was able to be a part of this for even just 24 hours. And just to have this glimpse into what life is like in the desert of Nevada was just really cool and valuable.

Paddy: For a horseman like Will, as enjoyable as the company of other humans can be, nothing really beats being out in wild country with Chicken Fry and Badger.

Will: The best days would be when I woke up before dawn and it's just Chicken Fry and Badger and I. And I wouldn't see anybody all day. High temperature, 75 degrees, a nice breeze to keep down the flies, nothing but open country to look at. And all I would hear are the footsteps of the horses.

And this wonderful sense of solitude to do nothing but sit there and think about the American West, to think about myself, to think about my horses. and eat snacks in the saddle.

Those were the best days. 

And then I would get into camp, put up the electric fence around the horses, lean against my saddlebags, have a sip of whiskey, make a can of beef stew and fall asleep looking up at the stars, hearing chicken fry and badger breathing right next to me. That was the absolute best.

For me, this is like a dream come true,

Paddy: On September 22, 2019, Will, Chicken Fry, and Badger made it to Sacramento, the end of the Pony Express Route. It had taken them 139 days.

Will: It was such a feeling of accomplishment, and I was so relieved not to have to plan anymore campsites. I was so relieved that Chicken Fry and Badger were off the clock. They finished their shift, they were done.

So this is a huge feeling of relief and satisfaction. Uh, I was like walking on the clouds, I was like, I crossed the west. What you gonna say, buddy? It didn't matter. I was, I was like really psyched. I was like, you can't touch this.

And I knew that like one of the best summers of my life, one of the most amazing trips of my life was coming to an end. And I was never gonna ride across the west again.

We're never doing that again,

And I didn't want to be back in Missouri, but boy, I missed this romantic notion where you could ride up to a ranch with two horses and camp there for the night and then ride out the next morning before dawn.

Paddy: In his book, Will wrote that he wanted to retrace Pony Express because it was his "avenue to understand the American West." He says he wanted to become a traveler in his own country.

Will: What I really wanted to do was to make a cultural cross section of the West. I think that the best way to interpret landscapes is through the people that live there, through the humanity.

And I consider myself a part of the West and an active participant in it. And to help other people better understand the West, this would be a way for them to see the West in an authentic, sort of organic way.

Paddy: The Last Ride of the Pony Express is a uniquely captivating portrait of the people, land, and history of the American West–one that could only have been created by a modern day horseman with the gumption to take on an outlandish endurance challenge

Will: And so my understanding of the West is way more complete and enhanced than it was on May 4th, before I started that whole deal.

What I came away with, is a sense of place that spans the whole West. Having traveled so slowly, I can now see every mile of country between Missouri and  California, so that I have images and people and experiences that come off every mile like annotations.

Paddy: Do you feel like a part of the landscape? Do you feel like part of the history and also maybe part of the future?

Will: Absolutely. So this book is a contribution to the written record of the American West, as I saw it. And so therefore, a contribution to our identity and therefore that makes me part of the future.

I'll bet you that if you ask someone who's walked the Pacific Crest Trail or the Continental Divide Trail or the Appalachian Trail, that they feel like a veteran of it now. They're like on the other side of the fence. I'm just glad that I could weigh in for whatever it's worth. It's, it's worth something to me.

Michael: That's Will Grant, speaking with producer Paddy O'Connell. Will's book is The Last Ride of the Pony Express, available in all the usual places for books. You can follow him on Instagram, he's @willgrantofthewest.

Paddy produced this episode, which was edited by me, Michael Roberts. Music by Robbie Carver.

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