From Cowtown to the Queen City

There's something quite spectacular about driving across the Prairies. The horizon stretches further than you ever thought possible, the sky takes centre stage, and every small town you roll into has a story to tell. The Trans-Canada highway from Calgary to Regina is one of Canada's most overlooked road trips. But once you know what to stop for, this drive turns from a simple stretch of highway into a journey worth taking more than once.

First Stop – Medicine Hat, AB – 2.5 hours from Calgary

You’ll need a camera for your first stop here in Medicine Hat. It’s hard to miss the World's Largest Teepee as you drive into town. It’s a towering 20-storey steel structure that pays tribute to the Indigenous peoples of the region. Its size is impressive and definitely worth a quick stop. Fuel up for the next leg at M.T. Nest Café & Market. You can find this local gem on the south side of the hill at 266 4th Street SW. This cosy neighbourhood café is known for fresh, house-made lunches and great coffee that will perk you up before getting back on the Trans-Canada Highway.

Second Stop – Swift Current, SK – 4.5 hours from Calgary

Swift Current is your official Saskatchewan welcome, and there’s no better way to mark your arrival than a quick stop for ice cream at the local gem, Dairy King. Try their famous “All the Bells and Whistles” twister, packed with banana, pecan, Skor, and cheesecake, then crowned with whipped cream and caramel.

If you’re needing a bit of a walk after all that ice cream, head over to Elmwood Park for a stroll along the creek. As Swift Current’s oldest park, it’s the perfect place to take in some fresh prairie air and slow down the pace. Travelling with kids? There’s also a great playground nearby where they can run off that pent up energy.

Third Stop – Chaplin Lake, SK – 5 hours from Calgary

One of Saskatchewan's most surprising stops is Chaplin Lake. It is one of the most important shorebird staging areas in North America. Chaplin Lake is Canada’s second-largest inland saline lake and attracts tens of thousands of migrating birds each spring and fall, including rare and internationally significant species. Even if you're not a dedicated birder, pulling off here for fifteen minutes to scan the flats is quietly awe-inspiring. Bring binoculars if you have them!

Fourth Stop – Gull Lake, SK – 5.5 hours from Calgary

Need to shake out the road legs? Kinette’s Corner Mini Golf in Gull Lake is a charming, community-run stop that's perfect for families or anyone who enjoys a little challenge. A quick round here is an easy way to break up the drive and enjoy a bit of low-key fun in the middle of the Prairies. The kids will love it. The adults might love it even more.

Fifth Stop – Moose Jaw, SK – 6.5 hours from Calgary

This is the road trip's crown jewel stop, and Moose Jaw delivers on every level. You’ll need to start with a mandatory photo with Mac the Moose, the enormous sculpture standing guard at the edge of town. At over 9 metres tall, Mac is the world's largest moose statue and an icon in Saskatchewan.

Next, head underground with a visit to the Tunnels of Moose Jaw. Experience guided theatrical tours of the city's legendary tunnel network. From tales of Chinese immigrants evading persecution in the early 1900’s to prohibition and Saskatchewan’s connection to Al Capone. The tours are dramatic, educational, and entertaining. Be sure to budget at least 90 minutes here.

Last Stop – Regina, SK – 7.5 hours from Calgary

Congratulations! You've made it to Regina! Start with a walk through Wascana Centre, where the lake, trails, and open green space make it easy to unwind after a long drive. There, you’ll also find the Saskatchewan Legislative Building, sitting on the edge of the lake. This is great spot for more photos, as the building is known for its spectacular architecture.

Downtown, you’ll find a growing mix of local cafés, breweries, and restaurants. It’s an easy city to explore at a relaxed pace, with enough variety to fill a day or two without feeling rushed.

The drive from Calgary to Regina is less about getting from point A to point B and more about everything in between. With the right stops, it turns into a relaxed, rewarding road trip across the Prairies.