My week as a real Calamity Jane on a cattle drive in Montana

In my 20s, I worked as a news journalist at a regional paper called The Daily News in New Plymouth, New Zealand.   I earned the nickname Calamity Jane because every time I was on late duty, a major disaster happened – a gang shoot-out, an ammunitions warehouse on fire, capsized Korean fishing vessel, six car pile-up, a cyclone … you name it, I covered it.  The Chief Report would ring the police and fire brigade to warn them I was on late duty. It was that bad.

But this story isn’t about my journalism days or the disasters I covered.  It’s a true wild west story of adventure and cowboys and it’s about  my moniker  – Calamity Jane – a nickname I still haven’t managed to shake off, despite not having worked in the Daily News newsroom for more than twenty years .

For those who don’t know, Calamity Jane was a gun-slinging, fearless horse-riding American frontier heroine and professional scout best known for her love of Wild Bill Hickock and for fighting Indians.  She roamed the plains of Wyoming and Montana and was skilled at both horse riding and gun shooting.   She was wild, romantic and free … a true feminist, adventurer and a woman who had the respect of the other cowboys.

Like Calamity Jane I had always yearned for adventure. I wanted to roam the world, to discover new horizons and challenge myself.   Which is why I decided to ride horses in America – Calamity Jane style – and truly live up to my nickname.

I researched the trip online, found a company called Ranch Riders in Leicestershire who booked everything and a few months later – bam, I was on a week-long cattle drive in the middle of remove Montana surrounded by real-life cowboys, wild mustangs, black bears, dusty ranches, red canyons, elks, hairy cattle dogs and horses that could bound up rocky outcrops like goats.

This was Dryhead Ranch – one of the most remotest places in Montana, big sky country, 4000 m above sea level, 35 miles on the Montana/Wyoming border and three hours from the nearest airport at Billings.

Myself and nine other guests which included ranch owners from Brazil and Upstate New York, a French airline manager based in Dubai, a 72-year-old attorney from California, a Dutch man and his 12-year-old daughter who rode better than all of us, an HR specialist from Holland and a Spanish yachtswoman, had all flown to mid-west America to become cowboys and girls for a week – City Slickers style.

Our job was to ride with the real cowboys and drive a herd of 250 stroppy cows and their calves from the winter pastures in Wyoming, to the Spring and Summer pastures in Montana – at Dryhead Ranch nestled at the foot of the snow-covered Pryor and Bighorn Mountains.
This wasn’t one of those ranches where you pretended to herd cattle and locals dressed up as cowboys and Indians for tourists, this was a real life working ranch. We would be braving the elements, riding for 4 – 8 hours a day and covering some of the most inhospitable but breath-taking scenery we had ever seen.  In short, we would be living like the real Calamity Jane.

Before we arrived, we were given a long list of items we’d need – cowboy hats and stampede strings, spurs, saddle bags, chaps, chinks, checked shirts, riding boots, thermal underwear, bandanas, sunscreen and riding gloves.

As we were going to be staying on an Indian Reservation, we couldn’t take any alcohol or bare our skin due to Federal Law, which was fine by me as I had absolutely no plans to drink and ride, or travel Lady Godiva style.

In fact it was so cold that I basically wore every piece of clothing I could find in my suitcase – six layers and a borrowed oversize rain slick – so that I looked like a cross between the Michelin Man and the Man From Snowy River.

Today, four generations live and work the Dryhead Ranch including Iris, her daughter Jennifer and her son Tyler and son-in-law Jake who are the real-life cowboys. They are all expert riders, have incredible knowledge about cows, horses, ranch life and Montana and live an enviable and amazing lifestyle that has almost mostly disappeared in the Mid-west of America.
Dryhead is a 32,000 acre working ranch with 150 American Quarter horses and 900 cows; it offers cattle drives, horse drives and ranch weeks and each summer the family hosts between 250 and 350 guests.

Our first day’s drive started near a bentonite mine in Lovell, Wyoming where, we were told, bentonite is taken out of  the Bighorn Mountains and made into a number of bizarre absorbent things such as kitty litter tray liners and baby’s diapers.

We drove the cattle for 50 miles past bentonite trucks, under huge power lines that stretched as far as California, across red and grey dusty plains, through a rocky canyon, over cricks, up steep paved or dirt roads, underneath jagged cliffs, past huge patches of white snow and onto the pastures of Dryhead.

The landscape was both intoxicating and intimidating. The harsh, dry dusty plains with very little vegetation, seemed to go on forever and we were constantly aware of the Bighorn and Pryor mountains looming over us and the mind-blowing canyon – sheer cliffs towering 1000 feet above a ribbon of green/blue  water – which cut a swath through the earth.

Jennifer followed behind in the pickup truck with our picnic lunch while one of the cowboys drove a cattle truck to pick up the stragglers and any horses (or riders) that got tired.

Despite the fact we City Slickers must have asked the same questions that every other guest has asked over the years, the family never appeared frustrated or sick of saying the same thing. They made us feel as though you were part of the family, helped us saddle our horses every morning and treated us as though we were the first guests they’d ever had.

On this particular drive, we were also accompanied by a very mysterious cowboy – think Clint Eastwood meets the Marlboro man. He was very good-looking, an incredible horse rider, his three cattle dogs obeyed his every command and we would stare slack-jawed in silence as he cantered by and lassooed a calf effortlessly.
Even his young sons, both wearing the full cowboy gear, proved to be amazing riders even though their saddles were munchkin size.

Real cowboys are a dying breed in America so it was amazing to witness them in action and see how much they really love and value the animals and their way of life.

“It took two generations to make the cowboy and it will take many more to lose him,” wrote the famous American West Artist and Writer, Will James (1892 – 1942).

We rose every morning at 5.30am and, like a breakfast fashion parade, checked each other’s outfits out; who had the shiniest spurs, the biggest Stetson, the most colourful cowboy boots.

It was all I could do to stop myself from whistling the Wild West theme as we clinked in our spurs to the cookhouse for a meal of the most delicious French Toast, Pancakes, Waffles, Eggs, bacon and hash browns I have ever tasted.

Admittedly, as far as the style stakes go, I was no Calamity Jane – in fact I wasn’t even a proper pretend cowgirl.  I wore a hard hat because I was scared of falling off my horse, I took photographs like a tourist from the back of my horse (very un-cowboy like behaviour), wore English riding boots and spurs that match. I also wore a huge brown rain slick that covered me and my horse like a portable tent. I’m amazed I wasn’t bucked off I was so uncool.
But what I lacked in style, I made up for with some of the best western riding I’ve ever done. There were long days in the saddle chasing after runaway cows, cantering down steep hills and climbing through rocky canyons.  I drove my horse in and out of thick shrub, up and down the side of ravines, and at one stage, I got so brave I thought I’d even try lassoing a cow until I realised that the animal would probably rip me off my horse and stomp me into the red dust.
Above us huge black raptors rode the volatile air currents looking for rabbits; elk and deer bounced off into the distance and wild Mustang, their manes blowing in the wind, stood rigid staring at us as we drove the 250 dusty throng of mooing cows across the incredible landscape. We even saw a small black mother bear with her baby cubs – two small balls of fur that bawled at their mother as she shuffled them along to safety. It was so surreal, I still can’t believe it actually happened.

They have three types of Cattle Drives at Dryhead – the Spring drives from Wyoming to Montana, the Fall Drives from Montana back to Wyoming as it’s too cold to leave the cows at Dryhead over winter, and the Horse Drives which are apparently a lot faster – horses are known to cover ground in half the time of cows. In fact, from what I saw, the cows seemed to spend most of the time walking back through the herd and bellowing for their calves.

At the end of nearly every day’s drive, we had to sit patiently with the herd while the cows mothered with their calves otherwise they would run off at the first sight of grass, eat their full and then suddenly remember their babies.  Cows really are that stupid. They’d then try to run back to the last place they saw them – which in our case was about 8 hours back to Wyoming – or they’d lose their calf somewhere in the vast plains never to be seen again. So we had to wait until they’d all found each other and the mooing had stopped.

During the drive, I noticed lots of mother cows with short-term amnesia in the front of the herd while their poor calves staggered along at the back.

The din of mooing did nearly drive me insane on our first day; give me London traffic any day. AT times, the herd was so noisy it sounded like 250 Wookies (think Chewbacca from Star Wars) and motorcross bikes all growling and revving at once.

We stayed at Dryhead ranch each night – mostly because it was too cold to camp out and a warm bath and a soft bed in the bunkhouse or cabins were a huge welcome after a freezing day in the saddle.  We’d corral the horses and cattle, drive back to the ranch and then start the next day from where we’d left them.

We totally lived the authentic cowboy lifestyle – pitching hay to the horses in the paddocks, trying to lasso the steel practice cowhead in the yard, telling stories around the camp fire and most nights after a fantastic meal by the resident cook, Donna,  watching back to back episodes of Comanche Moon or Lonesome Dove before bed.

I even found myself saying ‘howdy’ to everyone. All the guests bonded over a shared passion for horses, adventure and the fact we all had aching muscle

One evening I  stumbled back to my cabin through a mild snowstorm to find about ten yearlings all sheltering under my porch with their bums facing outwards like they were in the middle of a pow wow. I had to fight my way through them to reach the steps to my cabin and eventually drifted off to the sounds of small horses snorting, farting, squealing and occasionally kicking the wooden porch in the blackness outside.

My cabin was basic but warm and clean with a private bathroom, bath,  double bed and cowboy paraphernalia everywhere from lassoos, old cowboy boots and spurs hanging on the walls to cow and horse skeleton heads on the ground outside.  The cosy bunkhouse, with shared bathroom, slept about 8 people and was heated by a central woodfire stove.

On the drive, our herd of hardy, friendly and good-natured horses carried us for miles and miles and never once bucked or bolted – even when I sang ‘Home on the Range’ and ‘Rawhide’ very loudly or tried to make them run away from the cows.
 I had three different horses – old John Blue for the first day who seemed to delight in biting the cows if they got too close, Smithy who spent the whole time racing to the front of the herd and refused to turn back and Patches who turned out to be my favourite despite the fact I initially thought he was too fast.
Although I had to drive Patches into the herd a couple of times to get him to slow down, Tyler assured me that I would love this sweet horse by the end of the day and indeed I did; so much that I was trying to figure out how I could sneak him back to the UK.
We were all given instructions about where we should station ourselves alongside the herd. At the back with the dogs, the calves and the dust; at the side to catch any cows that wandered up the banks in search of grass; or at the front leading the melee forward.  We were told never to chase a cow that took off behind the herd and to let the mooing cows searching for their calves keep walking.
The rest – how to use spurs, neck rein, how to take photos on a moving horse, was pretty much left up to us.  Jake and Tyler seemed to know which kind of horses would suit our personalities and skills and we were matched with the right ones each time.

By the end of the five days we were galloping, turning sharp corners and rounding up cattle like pros …. well, at least we thought we were.

Driving the cattle into Dryhead Ranch on the final day was one of the most exhilarating moments of my life, even when Patches decided to race into the creek for a drink along with the entire herd of cattle. Our last day we took the herd on to one of the top pastures above the ranch and spent the afternoon meandering over the property looking at fences and checking out the herd of mares.

And then all of a sudden it was time to go back to the bright city lights of London.  The adventure was over.

On the last day, as we drove from the ranch back to the small town of Billings for our flights home, I gazed up at the snow-covered Pryor Mountains and thought of how far I’d come from those days as a night shift worker covering disasters at The Daily News.  This was definitely the adventure of a lifetime and despite the fact I didn’t fight any Indians or fire any weapons, I hoped the real Calamity Jane, wherever she is, would have been proud.
    Dedicated to my adventure loving brother Marc who rode waves until the very end . . . . (1961 – 2013).
Total flight time: 14 hours; Drive time: Three hours; Time in the saddle: more than 40 hours.
Tips, costs and how to get there:

A week at Dryhead is not cheap at around $1700 US dollars but worth every penny.   Flights from London to Billings via Minneapolis are around 800 US dollars. We also stayed in the Best Western Hotel in Billings for £75 per person a night.

  Thank you to the amazing photographer, Cassie, for some of the images above.  An abridged version of this story was published in the March issue of Your Horse

(c) Jane Wynyard 2013



  1. Brilliant post, Jane. You are fast becoming my hero, you know! Great writing and so glad you got to live one of your dreams for real. Hugs, Karen xx

  2. Great Blog!
    Glad to have been part of this big “Calamity Jane Adventure” 🙂

    Helene xx

  3. Great to have shared the experience with you Helene. I laughed so much that week thanks to you 🙂 …. will always remember our new nicknames (courtesy of Frans) – Giggle & Giggle. Here's to the next Cattle or Horse Drive! xx

  4. It was a pleasure to meet you all and experience the time of my life. I hope we can all do it again sometime. It was a childhood dream come true for me.
    They are truely great people that work at the Dry Head Ranch.

    Steve S.

  5. Great to meet you too Steve. I thought everyone on the trip was so much fun which made it even more special. Helene and I are VERY keen to do a Cattle or Horse drive again so let's all keep in touch.

  6. Hi Jane

    This 72 year old attorney enjoyed your blog very much. Your spirit and resiliance are inspiring. As the only one of thle group to get unhorsed, it was great to see that horsemanship and the cowboy dream is as alive (or more) in world citizens as in U.S. citizens. The very best part of the trip was the wonderful people that I met.


  7. Thank you John. I so loved meeting you – you are a huge inspiration. Thank you for all your kind words and support recently too. Look forward to riding beside you again in the not too distant future. x

  8. Sorry to hear about your experiences in Montana. You should try Dryhead – great fun and you won't be disappointed. Thanks for sharing your blog about riding in Botswana. That's next on the list! 🙂

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