Horseback riding travel & more in Saskatchewan

Let’s be clear: this post isn’t solely about finding horseback riding travel adventure in southern Saskatchewan’s rolling Cypress Hills. It’s definitely got a big ol’ section devoted to it, but there’s so much more here — because there’s so much more to Saskatchewan. Which, by the way, I’d been mispronouncing my whole life. It is, for the record, su-SKAch-oowen, not su-skach-ooh-WON.

So, even if you think you’re just planning to horse around in this Canadian prairie province — whether on a western trail ride or in an equine-assisted therapy session — I think this map and what’s about to unfold below will convince you that a southern Saskatchewan road trip is in order.

And if you think of Saskatchewan as one long, flat province…think again.

Horseback riding travel & more in Saskatchewan

Here’s a map to help you orient yourself and figure out whether to fly in and out of Regina, Saskatoon or use both airports like I did:

I flew into Saskatoon and out of Regina; and, as you can see from the map — which you can download and view both online and offline — you could do a nice, counterclockwise road trip starting in Saskatoon, then head toward Swift Current and briefly wind your way through Alberta down near Fort Walsh, and onwards to Maple Creek before going north again to Regina. You’ll need at least nine to 10 days to do everything listed in this entire loop at a fairly quick — but reasonable — pace, so if you have less time or like to be more leisurely, choose your favourites from this post and plan accordingly with the map as your guide.

And since that’s how my own Saskatchewan road trip played out, so too shall this post. Starting in…Saskatoon!

Things to do in Saskatoon

Saskatoon shocked the heck out of me. I don’t know what I was expecting but a hipster vibe with sophisticated coffee shops, artisan markets, boutiques and outstanding restaurants wasn’t it. I’d later figure out that it’s Regina’s cooler, younger sister. And, girl, she came to play.

In fact, the Saskatoon section became so robust as I started writing it that I had to turn it into a dedicated post, fittingly called “What to do in Saskatoon.” Head there to read all about the hotels in Saskatoon that I recommend (spoiler alert: it’s the Alt Hotel Saskatoon and Delta Bessborough), a run-down of Saskatoon’s best restaurants, including Hearth, Odd Couple and Primal, and why a visit to Pique is a must.

I also cover the Broadway and Riversdale neighbourhoods and point you to some of the neatest shops and eateries in each, like Alt Haus, Fable Ice Cream and Hardpressed Print Studio, and other awesome Saskatoon attractions that you shouldn’t miss, such as Wanuskewin Heritage Park, Meewasin, Black Fox Farm and Distillery and Lucky Bastard Distillery.

So keep on reading here, but please don’t forget to read about my visit to Saskatoon and get inspired to visit yourself; after all, it deserved its very own feature post, so you know it’s gotta be good.

Alive Sky Lodge

Near Rosetown, Saskatchewan, en route to Historic Reesor Ranch — which will feature strongly in this horseback riding travel story soon enough — if you want to fully unwind in the quietude of the prairies and fancy an overnight stay in a grain bin or a pet-friendly bunkhouse, Alive Sky will be your jam.

This working farm may offer guests opportunities to experience real farm life, but it’s subject to change day to day; keep in mind that activities are seasonal and the farming comes first, so if you have your heart set on hauling grain, temper your expectations. What you can count on is tranquility, hot tubbing and farm-fresh breakfasts delivered to your room (unless you’re staying in the Alive Sky Lodge, in which case it’s served in the lodge kitchen). Bring your own food or upgrade your stay with charcuterie boards, soups and or desserts available to all guests for additional fees.

The dog-friendly Cowboy Bunkhouse is the newest lodging at Alive Sky and it’s a quaint, self-contained space with a queen bed in one room and a twin bed that doubles as a sofa in the living room. There’s good air conditioning, a small but very functional kitchen, private deck with a cold plunge-style tub, barbecue. Wi-Fi and cable TV are also included! The Bunkhouse shares a large hot tub with the Alive Sky Lodge and we were the only ones using it during our stay.

If you prefer something more luxe, then you’ll want to stay in the Bohemian two-storey converted grain bin. With one queen and three twin beds, this “BINcredible” space offers a private hot tub for two, hammocks, a barbecue, fire pit with your wood included and a second-storey deck. There are even snowshoes included if you’re here when the Saskatchewan snowfall arrives. This is among the most interesting accommodations I’ve ever seen and if finding unique places to stay is part of your ongoing travel bucket list, then you’ll want to add the Bohemian to your itinerary.

PRO TIP: As you make your way through the prairies outside of the winter months, you’ll learn pretty quickly that it’s bug-tastic and your windshield is a certified bug killer. You’ll be tempted to use your wipers to wipe away the murder scene, but it’ll return just seconds later and all you’re going to do is end up with a big mess. So fight the urge and wait for a gas station, where you can use its tools to clean it properly instead.

Live the horseback riding travel life at Historic Reesor Ranch

This is what brought me to Saskatchewan in the first place: the horseback riding travel adventure found at Historic Reesor Ranch. And if it looks like this place is straight out of a Hallmark movie, that’s because it is. Sort of. You’ll be able to see “A Cowboy Christmas” yourself this holiday season.

It wasn’t even called “Saskatchewan” when WD Reesor first found his way from Markham, Ontario, to the Cypress Hills in the year 1900, where Reesor Ranch now sits. That would come five years later — after his wife, Alice, and four sons followed him by train to a more prosperous life, after a terrible storm wiped out more than half of their cattle and after WD and Alice started building a homestead that’s now part of the ranch house that still stands today. (You can read the rest of the family’s fascinating history here.)

For 125 years, this branch of the Reesor family has lived and worked here. Now in its sixth generation, they operate a guest ranch on what is a designated Provincial Historic Site — and they’re the first ranch in the province to do so. What you’ll find is warm cowboy hospitality, great home-cooked food and a special place in the Saskatchewan farming landscape.

The winding dirt road that leads to the ranch technically starts in Alberta — that’s how close you are to the border. But it all leads back to Saskatchewan. Don’t be surprised if you have a few friends join you on your drive to the ranch’s main doors; cows of every size and colour roam freely and the driveway is much more theirs than it is yours, so drive slowly once you turn off the main road.

Historic Reesor Ranch accommodations

There are enough rooms and cabins at Historic Reesor Ranch to host a wedding, house a big family reunion or a memorable corporate retreat, but if you’re just one couple or family, there’s a space just for you, too. We stayed in the newly converted Cypress Cabin, which opened this year to guests after a makeover. It used to be Grandma Reesor’s home, after all. It’s a well-appointed, cozy cabin with a king bed in a loft, double-over-double bunk beds in their own room and a queen-sized pullout sofa in the living room, plus a kitchen and bathroom with a shower feeding into a jetted tub — both with government-tested Reesor Springs Natural Spring Water running through its taps. You’ll never guess it’s only 300 square feet.

Outside, there’s a private deck with a barbecue and a propane fire pit with fire-engine red Muskoka chairs, all sitting under the Cypress Hills Dark Sky Preserve, where clear nights will reward you with the Milky Way arcing like a nighttime rainbow directly above your cabin. Bring a tripod along and the Northern Lights might even dance for your smartphone (even if you can’t see them with your bare eyes).

Packages to bring your horseback riding travel dreams to life

You can book accommodations and activities à la carte or indulge in a more all-inclusive-style Cypress Hills Cowboy Adventure Package — considered a Canadian Signature Experience by Destination Canada. Whatever you do, make sure you eat the steak dinner, served in the Ranch Hall Grill, which has all the makings of every cowboy or cowgirl dream you’ve ever had.

This is where our horseback riding travel life unfolded, as we reflected on our days spent on the ranch while the sun set outside, enjoying Saskatchewan beef, ranch-grown veggies and the most amazing baked brown beans cooked to perfection — all prepared and served by Theresa and Jason Reesor, the dynamic mother-and-son duo who run the place. It’s a steal at $45 per person. If you stay for breakfast, make sure you ask for some of Jason Reesor’s choke-cherry jam.

Activities at Historic Reesor Ranch are also priced fairly, with a two-hour horseback ride (available May 1 to October 31 for ages 10+) for $99 and one(ish)-hour ATV tours (available year-round, 16+ only drivers) for $89 per person. One of the things I liked most about the western trail ride experience at Reesor is that guests partake in getting their horses ready, including brushing and tacking up. I have plenty of English riding experience but a Western saddle has a lot more going on, so it was really cool learning something new about a world I’ve been part of since I was 15 years old.

Speaking of experienced riders, note that all rides at Historic Reesor Ranch are done at a walk. This is for safety and insurance purposes and it’s non-negotiable. (Trust me, I tried. Hard.) But this isn’t your typical nose-to-tail flat trail, so even though it’s also perfectly suitable for a first-time rider, you won’t be bored. Instead, you’ll head out in a small group into the spectacular Cypress Hills, quashing any rumours you heard about how flat the prairies are. In fact, here at Reesor, you’ll ride the highest point in Canada that sits between the Rocky Mountains and Labrador, a shocking 1,234 metres (4,048 feet) above sea level that’s been shaped by melting glaciers from the last Ice Age. The ride moves you in elevation and scenery, through pastures and woodlots to jaw-dropping lookout points. Oh, and you’ll probably meet another cow friend or two along the way.

Horseback riding travel benefits

It was at Reesor where I felt my body and mind relax from the flight, from the hustle and bustle of road-tripping, from the hurried pace that exists on nearly every trip I have the fortune of taking for work. In the laughter shared around the dinner table with Jason and Theresa; in the hearty pats I gave to Cowboy and Charlie, the ranch’s resident dogs who came to find us stargazing each night; and in the saddle — a place where I have always felt so at home — breathing in the fresh prairie air, it was here where I truly found Saskatchewan’s magic.

IMPORTANT NOTE: gratuity is not automatically added for housekeeping, meal services or horse/ATV rides. Please consider this when you settle up.

Visit nearby Maple Creek

Book an extra night and spend some time in the ranch’s outskirts, too:

• Conglomerate Cliffs — in the Cypress Hills Interprovincial Park’s West Block Wilderness Area, the cliff’s rocky banks fall into a valley rich with spruce, aspen and pine trees. Too many to count and like the best parts of your favourite landscape painting. There’s bring-your-own-horse equestrian camping at the park, so don’t be surprised if you need to share the road with riders on your way to the cliffs and be sure to keep a safe distance away from the edge; the rocks are small and loose and you can easily lose your footing fast

• Fort Walsh National Historic Site — though it’s only officially open during peak summer months, even after Labour Day weekend you can still park and walk the grounds of this preserved 1870s fort

• Adorable Maple Creek — first a winter campsite for workers building Canada’s first transcontinental railway in the early 1880s, the town of Maple Creek grew quickly and, by 1903, had its own mayor. It’s a small downtown strip but has a lot to offer and is worth the jaunt from Historic Reesor Ranch or as a pitstop on your way to Regina. Grab a locally famous London Fog from The Daily Grind and just wander; if you have kids with you, the Cowtown Kids and Candy store will make them feel like, well, a kid in a candy store — head upstairs to check out its enormous selection of board games; Broken Spoke Fine Art Gallery, run by artist Blaine Filthaut, is a kaleidoscope of art and wares and even has kid-friendly “panning” in the back of the shop; and if you need to look like you just walked off the set of Yellowstone, Hill Country Clothing is a must-stop

Things to do in Regina: where to eat, play and stay

Oh, Regina. Although its name has long been the butt of elementary school jokes, Saskatchewan’s capital city is no laughing matter. While it doesn’t have Saskatoon’s vibrant energy, there’s still enough to do, see and eat that it makes adding Regina to your Saskatchewan road trip worthwhile.

The best hotel in Regina

I stayed at what is arguably the best hotel in Regina — The Hotel Saskatchewan. It’s an Autograph Collection property that comes with all the trimmings you’d expect from that designation, like a grand lobby, great bar and nicely appointed rooms. Built in the 1920s within easy walking distance of some of the city’s best restaurants and the local shopping mall, The Hotel Saskatchewan’s room are upscale with regal crown moulding and wainscoting, marble in the bathrooms and comfortable robes to use during your stay.

I loved the pillowtop mattress in my room and the crisp cotton bed linens were so fresh and clean when I finally rolled into them after a long day.

Regina restaurants

Not to be outdone by Saskatoon, my short time in Regina proved that its culinary scene is worth visiting, too:

Avenue Restaurant and Bar

One of Chef Dale Mackay’s (of Top Chef Canada fame) three restaurants in the province, shared with expert mixologist Christopher Cho, Avenue is the pair’s only restaurant in Regina. It’s got a sultry, brooding bar-like atmosphere with a drink and food menu that could easily fit into the Toronto or Manhattan scene.

If it’s a toss-up between wine and cocktails and you’re only having one, make it a cocktail. They’re creative and well balanced with nice presentation. The slow-cooked pork belly press, with a sushi-like presentation, was so good I took leftovers back to my hotel room for a late-evening snack, which is pretty unusual for me on a trip where I’ve been eating out three times a day. And though Avenue is known for its beef wellington, I couldn’t resist the allure of the braised short rib. The rhubarb and vanilla mille feuille was the perfect ending.

Crave Kitchen + Wine Bar

Crave Kitchen + Wine Bar is housed in what was once the Assiniboia Club, a private men’s club that opened in the late-1800s when Saskatchewan was still part of the Northwest Territories. Women couldn’t even access the main dining room until 1972 and, thankfully, evolving times meant the need for such a club went by the wayside.

The best thing I ate in Saskatchewan featured on a charcuterie board we enjoyed at Crave: pemmican. It’s a historically significant Indigenous recipe that traditionally uses dried meat like bison or moose mixed with tallow (animal fat) and Saskatoon berries. It didn’t taste like diet food — and I didn’t care. The stuff is so mouthwateringly divine that the restaurant offers it for sale by the litre.

I had two daily specials, both from the bar and the restaurant — a peach concoction using fresh peach puree and coconut milk that I sucked down in no more than four gulps because I just couldn’t help myself and a gorgeous lamb shank. The buffalo mozzerella is a small, artfully prepared appetizer best for one person or two people with small appetites. It’s covered in balsamic pearls, which always feel so luxurious on a plate.

Rebellion Brewing Co

Squarely in Regina’s up-and-coming Warehouse District, beside what will eventually be known as The Yard, Rebellion’s beer evolution has been going strong since it started with only a few varieties in 2014. It even grows its own cherries now, which you can enjoy in a $13 can of Cherry Lambic or the taproom’s yummy take on the classic Singapore Sling.

Tangerine

Rise and shine! Tangerine has a beautiful selection of breakfast-y things and baked goods (the lemon loaf is where its at!), espresso-based bevvies and lovely lunchables. I grabbed a dill pickle egg salad sandwich for the road and it both travelled well and hit the spot.

The Everyday Kitchen

Sourdough everything! And decaf espresso drinks (which I’m adding as a notable feature because it was shockingly hard to find across Saskatchewan)! If you want to spend time in a cool space with great light and eye-catching décor, this will do the trick. Just make sure you order a sourdough cinnamon roll, because WOW.

Things to do in Regina

Horseback riding travel (adjacent) at R Connections

OK, OK, it’s not technically in Regina — but it’s only 15 minutes away — and, alright, it’s not on horseback either, but R Connections should not be missed as part of your horseback riding travel escapades in Saskatchewan.

In fact, my time here was such a massive highlight of my visit that I would go back to Saskatchewan just to do more equine-assisted learning with Carrie Ross at R Connections.

But first, what is equine-assisted learning? Incorporating a variety of activities and treatments, which may include something as simple as greeting or grooming a horse, this type of therapeutic learning promotes both physical and mental health for its human participants. Horses are naturally sensitive and intuitive, and facilitators are trained to respectfully integrate them into programming. It isn’t designed to replace traditional mental health therapies but rather to complement it or offer a different way of learning for those who aren’t necessarily seeking mental health support.

Jack, Andy, Pontiac and Bentley — four special horses at R Connections — help Carrie with each session, guiding the pace and direction in many cases. In some ways, they’re the leaders and Carrie is merely an eager interpreter. There are more than 30 different programs available to customize, whether you plan to participate on your own or with a group, with sessions targeting things like women’s wellness, self-confidence, leadership skills and more. You can book Carrie and “her boys” privately or take part in one of her many workshops, which range from a couple of hours to a couple of days.

Meditation with horses

We participated in a meditation with horses session, centred around mindfulness and self-care. Starting with some gentle chair yoga in R Connection’s purpose-built red barn to relax and try to connect with the present moment, we then moved into the small arena with Jack and Andy. As someone who spent 11 months learning how to meditate using an app, I assure you that it (still) doesn’t come naturally for me and I normally have a really tough time quieting what I call my “hamster-wheel brain.” But the calming presence of the horses, even though my eyes were closed most of the time and I had no idea where they were unless they were touching or breathing near me, did…something.

My focus sharpened even though my brain softened and I could feel an almost electrical charge fasten from my body to theirs. Sure, that sound hokey or “woo” or whatever other airy-fairy word you might want to use — but it was powerful. And transformative. At times, tears flowed down my cheeks and I didn’t even know I was crying until I had to wipe my face from salted tears that started to dry on my skin. This also marked the first time I’ve ever meditated and had any words of wisdom appear from seemingly nowhere, such as “it’s OK to slow down,” “try more patience” and “you are good and doing the best you can.” To feel those things emerge from within myself was the self-care I didn’t even know I needed.

Got bonus time on your horseback riding travel trip? Spend it at Manitou Beach

About halfway between Saskatoon and Regina — though closer to Saskatoon if you have no plans to hit Regina — you’ll find Watrous, Saskatchewan. During peak season (July and August), there’s a lot happening here. Arrive midsummer and you’ll find a nod to its resort-like beginnings in the 1920s, when Manitou Beach would be bustling with families playing in the sand and floating in its saltwater lake, known as The Dead Sea of Canada.

In its prime summer days, I’m told there would be artisans selling their wares, children running around with milkshakes in-hand and restaurants ready for your beachside orders. But should you arrive even a smidge past Labour Day as I did? Well, just forget it. You’ll have one restaurant and a desolate, chilly lake to contend with. Fear not, though, because you can still get your float on at the Manitou Springs Resort and Mineral Spa.

At Canada’s largest indoor natural mineral spa, three soothing temperatures (93-103°F) await in a large pool, that’s really three separate pools shaped like a lagoon. You’ll want to devote at least a couple of hours to the mineral pool, because it’s a hair more than $20 per person to get in — and add another $5, cash only, if you need a towel (of which you’ll get $2 back). The water from Manitou Springs is unlike anything we have naturally occurring in the Western Hemisphere; the only thing I’ve experienced that’s similar are the floatation pools that Le Nordik has at its Nordic spas in Ontario and Quebec, and those are manmade. If you’ve ever had trouble floating on your back in a pool, don’t fear: it’s impossible not to here. But beware — you might just fall asleep.

Check out the gift shop before you leave, and head to Mike’s Beach Bar across the road if you’re peckish after your therapeutic float. Don’t forget to drink loads of water the rest of the day and be forewarned that all that natural magnesium coursing through your veins is going to have a very relaxing effect, so you may not want to plan anything strenuous — including driving long distances — after this experience.

Interested in more adventure travel content? Check out these posts: Turkey Point Beach, Sunshine Village, Sugarbush Ski Resort in Vermont and Things to do Mt Tremblant.