Credit Left: Jared Chambers, Credit Right: Anais Wade

How is Paintrock Canyon different from your previous guest ranches in Colorado?

Scale-wise, it’s similar, but it has a lot more layers. There are more opportunities to experience day-to-day ranch work, like moving cattle, irrigating, fencing, and even observing baby calves being born. Paintrock Creek flows through the middle of the ranch, so guests have opportunities to swim and fish. We have access to one of the best fisheries in northern Wyoming and the rainbow and brown trout fishing is incredible. There is also great birding here. At the previous properties, we’d have to drive guests to trailheads for hiking, but we have so much that’s close here. And the vistas are so diverse. You have everything from huge mountains and beautiful rock formations to open prairie and the creek. The scenery is really multi-dimensional.

Credit: Anais Wade

What’s a typical ranch stay like?

The closest town is the speck of Hyattville, which is one-and-a-half hours from Cody and three hours from Billings, Montana. Guests arrive on a Sunday and depart on Friday for a five-night stay. We really cater to what guests are looking to experience. Some people want to ride a horse all day or help move the cattle. Some people want to hike. Others just want to sit and read at camp. We have 14 safari-style tents, all comfortably furnished and within a short walk to bathrooms and hot showers. I tell friends, this is not camping. You’re a 16th of an inch from nature all night long without being adversely affected by it. All meals are cooked outdoors over fire and served at communal tables. Our chef uses Ranchlands beef for many of the dishes. We also host wellness retreats, writing retreats led by notable authors like Molly Wizenberg, and workshops and clinics on everything from outdoor skills to stockmanship.

Credit Left: Claudia Elise, Credit Right: Megan Rogers

How are ranching and conservation intertwined?

Conservation is a product we produce, just like beef. We see ourselves as stewards of the land. It’s not an obligation, it’s an honor. From a business standpoint, the better we care for the land the more productive it will be. We graze our cattle in a way that restores the land, mimicking historic mobile herds. But it’s also a moral responsibility. When you live on the land you develop a relationship with it and the animals who live on it. You see a coyote every morning or the eagles nesting and want to protect them. People come here and it opens their eyes to how a working landscape can work in harmony with nature.

Duke Phillips was interviewed by Jen Murphy for All Roads North in April 2026.

To start planning your own journey through the American West, perhaps including Paintrock Canyon, please get in touch to speak with a Destination Specialist.

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At All Roads North, we believe that a place is nothing without its people. So often, when we ask our clients the most memorable parts of their journey, it’s not the Instagram-worthy landscape or acclaimed hotel that they mention, it’s the encounters they had along the way.  That’s why our trips are carefully designed to make those connections, providing you with an authentic and immersive experience. These experiences– whether it be with a local craftsman, musician, chef or marine biologist– are the inspiration for our Connections series, where we talk to friends of All Roads North to get an insider’s look at some of our favorite places across the U.S.

Tell us about your Jackson story?

I moved to Jackson in 2003 to work on a guest ranch and I decided to stay. I got a word from God telling me to move here– and I had never even been here before. 

What three words sum up Jackson for you?

Outdoor lovers paradise

What major Jackson Hole attraction lives up to the hype?

The grandeur of the Grand Tetons. They are absolute magic. They rise up in the distance and are so expansive. When you’re staring straight at the mountain range it’s incredibly humbling. 

What’s your favorite neighborhood to wander?

Wilson. It’s a little community in Teton county. It’s still a place where old timers, long time Jackson locals and newcomers all live. 

Underrated in Jackson Hole, overrated in Jackson Hole, and personal favorite?

What’s underrated is how close Jackson is to the wild. What’s overrated is that Jackson isn’t something here for everyone. This is an outdoor place. There aren’t many indoor options. There’s great restaurants and things like that, but there’s not really much to do indoors.

A personal favorite is a small cafe called Healthy Being Juicery. They have all fresh ingredients, and create their juices and nut milks in small batches. It’s just a small cafe. I love getting the bagel and lox. 

By Joeseph Haeberle

What’s your Sunday morning in Jackson Hole?

My Sunday morning looks like church, at the Presbyterian Church of Jackson Hole with my family. I’ve been going to this church for several years with my husband and children.

What restaurant do you take friends from out of town for dinner, a casual local’s favorite, and a weekend brunch?

I’d take friends to Local Restaurant. A favorite local’s spot is Persephone Bakery. And Cafe Genevieve is a great place for a weekend brunch.

Where do you go to get into nature?

I love to hike the local trails. These spaces are so special and precious to locals. I love to get a hard workout in a short amount of time and I love being outside. The sounds and smells, and the beautiful views of nature here. Sometimes I will be able to see wildlife, like deer and elk.

What inspired you to begin your hat business?

I had a similar experience entering hat making as I did moving out here. I heard a word from God in the middle of my happy life to do something different. Both times, it fully uprooted my life. I was working, then this idea to make hats entered my head out of the blue. I did an apprenticeship about a year after I had the idea, and I started my business in 2018. I could try to sound cooler and explain a more concrete reason, but it wouldn’t be true. 

This interview has been edited for length and clarity.

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In 1890, Sylvestor Wilson brought the first group of settlers over Teton Pass into what is now known as Jackson Hole. Six generations have passed, but the Wilson family still plays a pivotal role in keeping the Western spirit alive in Jackson through their work at the Jackson Hole Rodeo. 

Phillip Wilson, the great-grandson of Sylvestor, runs the rodeo with his three sons. Just about everyone in the family, including their wives and grandchildren, hold positions in the business as well. 

Phillip said the best part of rodeoing is that the whole family is involved. His sons and grandkids live on the same drive and huge family meals are the norm.

“We get to spend all day long on rodeo days with the grandkids,” Phillip said. “Those are the loves of our lives: our grandkids, the rodeo and the Lord. We’re blessed to have that ability to be with our family.”

Jackson Changing Over the Years

Clark Wheeldon riding a bucking bronco– three generations ago in the Wilson family.

Brandon Wilson, one of Phillip’s sons, grew up around ranching and rodeo culture his whole life. However, Jackson isn’t exactly the same place it was when Brandon was growing up in the 70’s. Over the years, the presence of the acclaimed ski resort grew and now the town plays host to plenty of out-of-towners and second home owners. 

“When I was a kid, all you had to do was talk to a friend and you could go find some place to find some calves, steers or some bucking horses to get on,” Brandon said. “It was a ranching community. Now, [Jackson’s] developed into this huge tourist mecca and the ranching is pushed out. So now there are fewer opportunities for the kids that want to ride bulls or bucking horses.”

The Wilson family provides the opportunity for young people to develop these skills and compete in their rodeo. Over the years, the Jackson Hole Rodeo has earned quite a name for itself. Kids come from as far as Australia and Mexico to work in town while improving their rodeo skills, whether it be barrel racing, bull riding or roping. 

Many young aspiring cowboys and cowgirls start with something a little bit more approachable– mutton busting. Children from about age five to six strap on helmets and ride sheep for as long as they can before falling off. 

The Danger Involved

A Bullrider at the Jackson Hole Rodeo

Brandon’s nephew, Levi Wilson, has long graduated from sheep and participates in the most dangerous event the rodeo has to offer: bull riding. The 23-year-old went to college on a rodeo scholarship. Now he’s graduated, Levi works with the family, helping to run the rodeos and tend the livestock, and hopes to soon ride bulls full-time for a living.

Over the years, he’s accrued quite a catalog of injuries– a shattered arm, a torn groin, a ruptured spleen– but nevertheless Levi said he’s never thought about quitting.

“You can’t ride bulls just so you can tell somebody you’re a bull rider or to pick up girls at the bar,” Levi said. “It has to be in your blood, like it’s all you can think about. So the little injuries can’t be something that slows you down.”

Brandon said that cowboys and cowgirls recognize the inherent danger of rodeo sports, but the camaraderie, the community and the thrill make it worth the risk for most competitors.

“It’s never going to be 100 percent safe, but that is also true of any sport,” Brandon said. “With football or skiing, there’s always going to be accidents. So we can’t make it safe, but what we can do is remove some of that danger by doing things like choosing the right animal for the right rider.”

Two Sides to Rodeo Animals

Jackson Hole Rodeo Rider

From bulls to horses to sheep, animals are essential components of rodeo life.

“These bulls are pretty much family,” Levi said. “We’re with them every single day. You grow a relationship there. A lot of our bulls are two completely different animals at home and uptown. These animals know their job and I think they crave it and love it just as much as the rest of us do.”

Brandon acknowledged that there is an assumption that rodeo animals are treated badly, but said “that couldn’t be farther from the truth.” There’s no motivation to mistreat animals in the rodeo world, he said. You want them healthy and ready to compete.

Leading up to the competition, Brandon said the bulls are fed 19% protein grain, which gives them a lot of energy. Plus, there’s something to be said about the energy of the rodeo competition itself that gets them riled up.

“At home, you can go up and scratch some of them, but then you get them into the rodeo and you get the lights going and the sound,” Levi said. “They know their job and they become a completely different beast. They psych themselves up to compete just as much as we do.”

Moving Forward

A few of the Wilson family members behind the Jackson Hole Rodeo.

Typically, the Jackson Hole Rodeo hosts 30 to 40 rodeos a year. In 2019, an astounding 44,000 attendees visited and Brandon said the family anticipated 2020 being their best year yet. 

But like so many other industries, the rodeo business was hit hard by the COVID-19 pandemic this past year. As live events across the country were cancelled, the rodeo’s revenue was cut off, but the Wilsons still had to continue the expensive tasks of feeding and caring for their stock.

However, as more people are vaccinated and prospects for travel seem brighter and brighter this year, hopes for reopening the Jackson Hole Rodeo again are high.

“I think [the rodeo is] a great way to enjoy our heritage as Western people,” Brandon said. “Just talking about the competition and the camaraderie of what rodeo is… I want more people to see it and experience it so they can understand what a great sport it is.”

Interested in going to a rodeo? Check out these sample Western itineraries:

Yellowstone and Grand Teton Road Trip

Going Wild in West Texas: A Private Ranch Road Trip

Images courtesy of Jackson Hole Rodeo website

The post Three Generations of Cowboys: The Family Behind the Jackson Hole Rodeo appeared first on All Roads North.

How did you come to be a rancher in Wyoming?

To be honest, I was born into it. I grew up on the ranch and this has been my life since the beginning. I went away to boarding school in California and then college on the east coast, as well as a spell running riding safaris in Kenya.

Did you think about moving away more permanently?

I consider myself really lucky to have had the option to move back to Wyoming. Pursuing a life in agriculture is not easy for a young person. You need so much capital to get started that unless you are in a position where you can join the family business, it’s hard to get started on your own. The town I grew up in, Dubois, has few sources of income other than tourism and agriculture, and tourism only lasts half the year. Most of my peers who wanted to start careers had little choice but to leave. So yes, I feel really lucky to have been able to experience life outside of Wyoming but then have the opportunity to come back.

So ranching in Wyoming is a hard business to be in?

It’s difficult. Bitterroot Ranch is a gem but if we were to sell it, the value of the land is in no way connected to its agricultural value. It’s purely recreational. So it’s really difficult nowadays to grow a ranch that is being operated on a purely agricultural basis. Many of the ranches are now owned by absentee landlords most of whom value the land for the landscape and wildlife. To them the idea of running a traditional cattle ranch would just be an aggravation. Unless you love the lifestyle, ranching is a lunatic business to be in.

Well you could always sit behind a desk all day…

It gives me tremors just thinking about it! But ranching can be tough and you can get stuck in a rut. But having guests here and being able to experience the ranch through their eyes, to see how different and liberating it is to them, breathes new life into my attitude.

You have guests from all over the world. What are they usually most surprised about during their time at Bitterroot?

I think it’s the space here. You can ride all day and see no evidence of human presence. You can look out over a landscape and see no roads, let alone traffic jams and power lines.

Another thing we hear frequently concerns the riding itself. Many guests have only ever ridden in a ring or in a very controlled way. When you’re herding cattle on horseback the focus suddenly becomes the cattle not the horse. Guests find themselves riding in a much more natural, subconscious way and rather than forcing the experience – they allow their body to work with the horse.

You said you have spent some time riding in Kenya. How do you think Wyoming compares to an incredible place like Kenya?

It’s the wilderness here and the ability to get away from it all. I think it is truly unique. We run some pack trips where we will ride out from the ranch for a full week. You can easily go for a full week and not see another human. Beside the odd grizzly bear or wolf pack, you’re on your own. These trips really appeal to some of our more well travelled clients.

You mentioned that you only spend the summer at Bitterroot.

Yes, Bitterroot is considerably higher and gets much more snow. So each winter my family and I move down to the lower ranch, about ninety miles from Bitterroot. It’s the same seasonal movement that has always happened in the west and indeed across the world. We used to drive the cattle on horseback all the way down but the route crosses an Indian reservation that we are no longer able to travel through.

Life at Bitterroot Ranch changes with the seasons

What’s the name of the local tribe?

There are two, the Shoshone and the Arapaho. The Shoshone actually made peace with the US government fairly early on in the colonization of the West and as a result were given a good reservation in terms of size and resources relative to some others. The Arapaho were more rebellious and it was only at a later date that they came into the reservation fold. The initial plan was for them to spend the winter on the same reservation as the Shoshone and then they would be given their own in the spring. That was over 100 years ago and they are still together. The two tribes were sworn enemies, so it is a contentious issue.

And do horses play an important part of their culture?

It obviously depends on the individual but there are some great horsemen and women on the reservation. Rodeo is also very popular among tribal members and I’d say that they make up the majority of the competitors at the local rodeo in Dubois. The young children may barrel race, the older brother will be bull riding and the grandfather team roping. It’s a very family oriented affair.

One of the greatest things I have ever seen was 3 year old children riding sheep at a rodeo in Montana.

Mutton busting! Our British guests always say that if that were to happen in the UK, the authorities would probably descend and start confiscating children!

Thanks Richard!

Sample itinerary: Yellowstone and Grand Teton Road Trip

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Having spent several weeks traveling through Wyoming and Montana, one issue that consistently came up when I spoke to people was the wolves and the impact of their reintroduction. Do you come down on either side of the debate?

I come at this from several different angles. I make my living as a wildlife guide and obviously seeing wolves is a really important part of that. That’s looking at it selfishly. But from a more practical point of view, wolves are a vital part of the ecosystem and they were brought back with a lot of vision and foresight. However it is certainly not without its problems. As well as being a wildlife guide, I am also an avid archery hunter. I kill and butcher all my own food. It has taught me how to harvest animals to sustain myself. I would say that most hunters, and of course ranchers, are 100% anti wolf. I’m not that way but I understand there needs to be a balance.

I think wolves are now an essential part of a balanced ecosystem, they help cull the herds and strengthen the gene pool by removing the sick and the weak. They were first reintroduced in northern Yellowstone. I can’t remember how many, 30 perhaps, but it was a small number and very quickly they started to re-populate. One of the reasons they were brought back in the first place was to control the elk herds, which were over abundant. Hunters may disagree but that was the opinion of most biologists. They were over-grazing, over-consuming and negatively impacting the ecosystem. While the elk population was initially slowly depleted it was actually another species, coyotes, that was impacted first. They hadn’t lived alongside wolves for 70 years and their population plummeted. As this happened, the population of another animals, the antelope-like pronghorn, rebounded. Adult pronghorn are too fast for coyotes but they do prey on the calves, so the relationship started to come back into balance.

The next thing that happened was that the elk population began to drop and as it dropped something really interesting happened. A lot of the vegetation that they had been consuming started to grow back and one of the first, or most significant, was willow, a riparian plant that grows near water. As the willow came back, songbirds, which had been gone from Yellowstone for decades, reappeared. The beaver population, which relies on willow to build their dams and lodges, started to recover. The fishing also improved, as willow flanks the river, cools the water and provides a habitat for the aquatic insects that trout feed on.

So I think the reintroduction of wolves has had a lot of positive impacts but it still requires management. You can’t introduce a top predator without having a control mechanism. After a decade of population growth the government relinquished their control and put the management in the hands of the individual states: Montana, Wyoming and Idaho. That’s where a lot of the conflict lies and each state has a different strategy. Today Montana and Idaho are going ahead with some limited wolf hunts. They have been very controversial but I think they are very important. Wyoming has gained and lost control of its wolf population several times. Most recently control has been handed back to the government. Ultimately I think this came down to bad management strategy. We listed too much of the state as a predator zone, areas where wolves could be shot on sight. The strategy is now being restructured, so that wolves can be controlled as a predator in areas where ranching is the dominant industry but are given greater protection in areas where tourism is more prevalent. The bottom line is that wolves are here to stay and the approach needs to be one of compromise.

It’s a fascinating debate and one that is starting to rear its head in the UK with the prospect of reintroducing wolves in Scotland.

It also seems that the wildfires are also another environmental hot potato.

To a lesser extent. We could talk about a fires, a changing climate, and water is of course always a big issue. We’re lucky here being at the head of the water system but it’s a huge issue throughout the West.

Down here (near Jackson) we have been relatively lucky with wildfires but the event that really changed things was the huge 1988 fire that swept through Yellowstone. Prior to this the approach had been to suppress even the smallest fires in an attempt to minimise the impact on tourism, but the whistle was really blown in 1988. They will now let the smaller fires burn naturally, which helps thin out the forest and hopefully prevent a much bigger fire from taking hold. Interestingly many of the tree species have what’s called a serotenous cone. They only release their seeds under the application of extreme heat. So fire is an essential part of the ecosystem.

It’s not really a question but on the subject of water, I was amazed that you can stand in Yellowstone next to two streams, one flows west to the Pacific and the other empties into The Gulf of Mexico.

Yes, it’s the Continental Divide. Guests are often surprised that it runs through Yellowstone, thinking that it marks the middle of the country rather than the divide between the two watersheds. You can drop a popsicle in two nearby streams and they will end up thousands of miles apart. The Yellowstone River actually runs north before joining the Missouri and then the Mississippi. The Snake River, near Jackson, runs West before joining the Columbia and emptying into the Pacific. It confuses people.

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