I am always given the problem horse.
"You've got to watch Sunshine," a wrangler in Texas once told me as I swung up onto a saddle. "He likes to bite the other horses."
"Cupcake likes to gallop a bit, but this is a trail ride, so you'll really have to keep her under control," I was told as I mounted a big roan in New Mexico.
Then there was the old, tired, one-eyed horse in Nicaragua that the stable owners didn't even bother to name. "She doesn't really like to be ridden and may try to brush you off against a tree," the owner said as he pointed toward the head of the windy mountain trail. "Just keep her away from the edge when her blind eye is to the outside," a stable hand counseled, soto voce.
So it was no surprise when, as I settled into the saddle on Coalie, a large, black gelding at the luxurious Paws Up Ranch, I was told he would be wanting to graze whenever possible, liked to nip at the other horses to show he was boss and was a bit "cowy" -- that is, he liked to bite the cows and steers we'd be moving during a two-and-a-half-hour cattle drive. "That's a good thing," the wrangler said. "But you'll know what to do if he begins to misbehave. You have children. You know how to discipline."
And so two of those children -- my sons, 12 and 14 -- and my wife and I set off under a Montana big sky that had been greatly foreshortened by smoke and haze from this year's wildfires. Under the leadership of a pleasant cowgirl named Cindy, our objective was to move a herd of cows and steers from one field to another, which would include directing them through a couple of gates and over a somewhat narrow land bridge. When we reached our destination, we would attempt to target a cow and cut it from the herd.
Coalie started out on good behavior, but once we reached the cattle he seemed more interested in eating than herding. I recalled the wrangler's advice: Discipline him as if he were one of my kids. "Coalie," I said sternly, "If you do that again, I will take away your phone."
I swear he turned his head and looked at me, then moved on.

A multistation sporting clay course included "pigeons" flying above meadows and "rabbits" skipping along the forest floor. Photo Credit: Arnie Weissmann
I was raised in Chicago and now live in New York City, but in between spent 21 years in Texas and am married to a Texan who likes to ride, so I've had some exposure to ranches and horses. Still, on a scale from 1 to 10, in which 1 is Billy Crystal at the beginning of "City Slickers" and 10 is John Wayne in "True Grit," I'm about a 2.5. I tended to like the ranch parties where the women went off to ride and the men stayed back and grilled, drank beer and pitched horseshoes.
After my firm words to Coalie, he was less in need of discipline and seemed to enjoy chasing down stray cows. We had been told that to herd a cow, you basically move toward it as if you are going to walk right into it; the cow will get out of the way. Shouting "hee-yah!" is completely optional. The trick is to get them heading in the right direction as they walk away from you, which simply means approaching them from the correct angle.
It turned out we were all actually quite good at moving cattle. Not so good at culling one off from the herd; only my wife came close.
Paws Up is one of a handful of luxury dude ranches in northwest Montana (guests fly into Missoula) that promise a taste of the Wild West with no small amount of pampering. At Paws Up, one can choose from five six-tent glampsites (for glamorous camping, in a one- or two-bedroom tent) or, as we did, one of 28 very well-appointed, cabin-style residences (eight of these also have adjacent tents). The cabins have touches of the rustic but are perhaps better described as "wilderness estates" (which is the name of one of the categories available).
At Paws Up, which had hosted my visit, you begin to understand why ranches are sometimes called spreads. Cabin guests are handed not only keys to their residence upon check-in but keys to a car (a Kia Soul) to get around the 37,000-acre property's homes and restaurants, activity center, spa, etc. (Glampers can call for transportation from the sites to facilities.)
Guests can simply relax on the porch of the estates or by a riverside campsite and watch deer in the clearings, raptors in the sky or, as happened once during our three-day stay, see a black bear trot past.

Fire pits went unlit at the height of last summer's fire season, but they still provided a social hub at the campgrounds. Photo Credit: Arnie Weissmann
But there are also a host of activities. In addition to the cattle drive, my family rode mountain bikes from a ghost town back to the ranch, shot sporting clays on a very well-designed, multistation shooting range and took up the challenge of a woodland obstacle course. And we spent a fair amount of time before and after meals at the tetherball and horseshoe pits near the two ranch restaurants.
Other activities on offer, some at extra cost and some inclusive, were fly-fishing, ATV tours, rafting, guided hikes, rappelling, archery, kayaking, paintball, canoeing, wagon-team driving lessons, chuck wagon dinners, waterskiing and a wide range of equestrian options. Helicopter tours of Glacier National Park and hot-air balloons can also be arranged, and rodeos can even be organized for large groups.
Some Montana luxury ranches do not allow children, but Paws Up welcomes them and offers programs for kids ages 4 through 12 as well as babysitting services.
Depending on one's timing, a guest might also be exposed to regional culture without leaving the property. Paws Up regularly schedules events that could be viewed as enrichment activities; on our first night there, drummers-in-residence guided a drum circle as guests gathered for a Montana Long Table dinner. As the name suggests, about 100 or so of us were seated at two very long tables and served a localvore menu, preceded by a mini-farmers market where area brewers, barbecue kings, Hutterite farmers, cheesemakers and picklers offered their products and produce for free (guests were encouraged to take whatever they wanted back to their cabins to enjoy later).
The property is experimenting with an app that's monitored by the concierge staff to respond to questions and make reservations for activities, but as co-general manager Nico de Lange acknowledged (and I experienced), it is still undergoing some "teething pains," due mostly to spotty WiFi. Outstanding issues, de Lange said, were being addressed.

The Blackfoot River Lodge has four bedrooms, and adjacent luxury tents if that's not enough. Photo Credit: Arnie Weissmann
Paws Up (the name is the historical name of the property, referencing the way that working dogs greeted the ranch owner) does a good job of offering something for everyone, where one can be as pampered or challenged as one wants.
This isn't the type of dude ranch where the owners try to replicate how early Montana cowboys lived. You'll eat way better than they did, sleep far more comfortably and will pay, rather than be paid, to move cattle.
I enjoyed the experience immensely and can tell you that sitting on a horse and shouting "hee-yah!" at sluggish cattle is as close as a city slicker can get to channeling John Wayne.
Or, perhaps, Walter Mitty.