Story and photos by Shawn Hamilton

On a perfect blue-sky day in the Kananaskis region of the Canadian Rockies, the views are nothing short of breathtaking in every direction. But my attention is fixed on the path ahead as I work to stay balanced in the saddle while my horse carefully navigates the rocky ridge along the mountainside. Reaching into my bag, I cautiously pull out my camera to capture a few shots. In that moment, I notice our guide, Dewy, fully immersed in the adventure, wearing an unmistakable grin beneath his ten-gallon hat and bushy mustache. Each day, he pushes his clients just beyond their comfort zones, creating memorable, thrilling experiences.

The Lost Trail Ride, one of the most popular adventures offered by Anchor D Guiding & Outfitting, promises a unique and unforgettable journey. Dewy Matthews, the owner of Anchor D, operates his ranch just an hour southwest of Calgary, Alberta. I’ve had the privilege of knowing Dewy for over thirty years, and his enthusiasm for sharing the stunning Western Canadian landscape with others has never wavered. Over the years, many aspects of the ranch have evolved. The Anchor D herd has expanded from 30 to 130 horses, the land has grown from 80 to 320 acres, with an additional 250 acres leased, and the original family home has been replaced with a spacious 2,050 square foot log cabin. However, Dewy’s love for guiding riders through rugged mountain terrain, winding trails, and expansive valleys remains unchanged. His infectious sense of humor and deep passion for horseback riding continue to make every ride a memorable adventure.

On the morning of my arrival, there is a flurry of activity at the ranch. Children and novice riders are mounted up for a two- or three-hour trail ride; trailers are loaded for a weekender ride; and our horses’ names are being checked off a list as they fill two long trailers for the Lost Trail Ride. After 35 years in business, Anchor D has every angle of a Western retreat ride covered. Some days there are as many as five rides on the go in various locations. There are a lot of wheels turning. Dewy manages to do it all outside of the digital era, meeting with his head wranglers over coffee in the morning, and peering over his glasses as he reads the daily details handwritten on paper.

Camryn gives us our safety talk aboard Shakoda, a beautiful 17-year-old Shire/Paint-cross gelding. The Lost Trail Ride is geared for the more experienced. Although we are all seasoned riders, we listen intently as she explains the dos and don’ts of handling, stopping, and moving the horses. Our gear is loaded and we jump into the trucks to follow the trailers west along highway 40 into the Kananaskis region of the Rocky Mountains, where our seven-day journey will begin.

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In the parking lot beside Cataract Creek we are handed our mounts as they are unloaded. For me, Dewy has chosen a beautiful dun gelding named Magoo — he takes great pride in matching the perfect horse to each client. “By the end of the ride, if my clients don’t want to steal the horse they are on, then I haven’t done my job,” he once told me.

Two percherons, Waylon and Willie, are hitched to the chuckwagon; our bags and the supplies are loaded in the back, and we get the OK to bridle and mount up. We watch Kelly and her assistant Brooke maneuvre the team pulling the chuckwagon across the fast-flowing Highwood River. Dewy’s son, Chad, leads us into the water on Stretch, a large black Percheron/Paint-cross. The water is deep in spots. One of the dogs loses his grip and goes floating down the river, eventually getting his footing and making it to shore. I lift my feet out of the stirrups to keep them dry. We let the horses drink before arriving safely on the other side. It is only a 20-minute ride to camp but just enough time for Magoo to test me — trying to eat grass on the path and trotting when the horses ahead of us trot. A gentle tug on the reins and a firm no, and we quickly come to a mutual agreement. 

Chad on Stretch (above), keeping a close watch on the river crossing.

Dewy is excited to show me the new location he has chosen for the Lost Trail Ride camp, and I can see why. There is a large cook tent, a fire pit, tents scattered throughout the woods, and a vista of a steep rocky ridge glowing in the sunlight. The river is an easy walk where one can bathe, swim, or if brave enough, go cliff jumping.

We get our bags from the wagon, claim our tents, and eat lunch before remounting for the afternoon’s ride up the ridge. The trail is steep and slippery due to the recent rainfall. I allow Magoo to pick his own footing — he knows his job well, and we soon reach the top. We dismount, tie our horses, and relax along the ridge taking in the stunning scenery of camp below and the surrounding mountain ranges. Everyone is slowly winding down from their trips; we’ve come from Switzerland, Germany, Hawaii, England, and various parts of Canada, and we’re a diverse mix.

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On arriving back at camp we loosen girths but do not remove the saddles, allowing the horses’ backs to cool down gradually. I jump in to help feed hay, eventually take the saddles off, and with a bucket and sponge wipe down the horses’ backs and girth areas before washing up for dinner. The well-being of the horses is always first and foremost with the Anchor D crew.

I am elated to see greens alongside the chili and potatoes at dinner — not something you always see on these backcountry trips as greens are difficult to keep. After a hearty meal, we help lead the horses to the river to drink, each of us taking one or two and walking them down the path to the water. Once back at camp, I take my seat around the crackling fire and listen to Dewy serenading us with his accordion. It’s the first of many instruments that will accumulate around the fire during the week. I eventually retire to my tent to drift off to the sound of the rushing river at the bottom of the ridge.

By the time I dress and exit my tent the next morning, the horses are already fed and tacked up. The smell of coffee and bacon wafts through the air. After a hearty breakfast, Dewy gives me a tip as I bridle Magoo: Always put the bridle over the far ear first, so that “if you accidentally pinch the last ear it will be the one closest to you and the horse’s head will swing away from you instead of towards you, bashing you in the face,” he explains.

With lunches and full water bottles in saddle bags, we mount up to head back towards the trailers where we can load up and drive to another trailhead. This setup allows us to see more of the region and experience different terrain every day. In the parking lot, Dewy asks us to walk in single file on the pavement as he listens for loose or lost horseshoes.

Today’s trail is steep and heavily wooded, but small openings in the trees allow for a quick scenic view. Intense rocky terrain finally opens up to a lush green valley spotted with colourful wildflowers, allowing us a nice canter to our lunch spot. Dewy points out the Elk Range to the west, part of the Continental Divide separating British Columbia and Alberta. “That’s where you will go if you come on the Great Divide Ride,” he explains. Sign me up I’m thinking! The views are stunning and although I have travelled throughout the world on horseback, I feel very fortunate to have some of the most beautiful mountainous landscapes in my own country.

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After lunch, we lead the horses down the steepest part of the trail on foot. For this, “both me and my horses thank you,” Dewy says appreciatively. Once the footing levels out, we mount up and begin the rest of the descent. Dewy and Chad are busy in the front with machetes, opening up and marking the trail.

After a long day in the saddle, and before heading back to camp we stop for ice cream at a small convenience store — a welcome treat. After dinner, Chad brings out his guitar and we all sing along to our campfire favourites. The night is clear and under bright stars I make my way to my tent where I fall asleep before my head hits the pillow.

The next day Dewy takes the team and wagon back to the ranch to participate in a parade in town. I’m thinking: What more can he possibly put on his plate?

When Dewy returns to camp in the driver’s seat of the rig, Chad’s wife Simaran and their seven-month-old son, Auberon, Dewy’s only grandchild, are front and centre for their inaugural stay at camp. It was worth the price of a flight to Calgary to watch Dewy bounce his grandson on his lap at the fire — a part of him one rarely sees.

Over the next few days, I thought the trails could not get any more difficult or the views any more stunning. Dewy had planned this ride perfectly. Just when you think you have done it all or seen it all, he takes you to places that blow your mind. Terrain challenged us a little more each day but rewarded us with some of the most spectacular mountainous views of all time. I had to pinch myself while sitting in the grass of the Mist Valley overlooking the snow-capped Misty Mountain range to make sure I wasn’t dreaming. Riding at an elevation of 8,600 feet, letting Magoo pick his way through the skinny rocky terrain with jaw-dropping views in every direction, I finally braved my fears and took out my camera for some photos. 

Lush green valleys are spotted with yellow hedysarum flowers, which Dewy explains are a favourite food of grizzly bears and an essential part of their diet. “They dig up the plants to get to the rich bulbs and roots,” he says. With further research I learn that the bears digging up these plants tills the land in such a way that increases the nitrogen availability in the soil, which benefits the flowers.

Crossing the river on the way back to camp, we take the horses as deep into the water as we can, “It’s great for the horses’ legs after a long day,” explains Chad.

After a 25 km day in the saddle and plentiful dinner of lasagne and caesar salad, I force myself to stay up to listen to the music by the fire. Each night more instruments come out — wranglers, cooks, everyone had a gig. An orchestra of accordion, guitar, violin, and fiddle plays under the bright stars of the milky way around the fire. A few guests get up to dance. It is the perfect night.

Dewy Matthews, owner and operator of Anchor D Guiding & Outfitting.

On our last full day’s ride, Dewy tells us it will be our easiest day. I roll my eyes. We follow him and his horse through narrow tight spots between the trees as he and Chad machete a path. After hearing Dewy yell from above “Go hard and stay right,” I take a deep breath and let Magoo negotiate a skinny path between the trees on flat rock uphill. I say in my outdoor voice: Are you kidding me, Dewy? But I know full well that there is an ear-to-ear grin hiding under the moustache. 

The author, Shawn Hamilton

We finally arrive at the rushing turbulence of Cataract Creek waterfall and enjoy a relaxing lunch. The trail home opens up with large meadows that allow us to gallop for long periods. Magoo enjoys it just as much as I do. 

The week went by quickly, and it was hard to leave camp and head back to reality. I owe my personal growth as a horsewoman, feeling more at ease in the saddle through difficult terrain, to Dewy for pushing me beyond my comfort zone and to Magoo for giving me the confidence to do so. I also return home with an increased love of my country and what it has to offer. I am thankful to have reunited with Dewy and his crew, sharing this adventure with the others and bringing home some of my most picturesque memories that will last a lifetime.

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