A Simple Drive, Done Differently

The Trans-Canada Highway west of Winnipeg doesn't always get the credit it deserves. Most people treat it as something to “push through”, with the windows up and cruise control on, assuming there is nothing to see. But that is where they are wrong. Between Winnipeg and Regina lies hidden river valleys, swinging bridges, small-town museums, century-old murals, and a bakery that will make you seriously reconsider driving straight through.

This is a trip that rewards the curious, and here's how to do it right.

First Stop – Brandon, MB – 2 hours from Winnipeg

Manitoba's second-largest city is your first stop. The Riverbank Discovery Centre sits right on the Assiniboine River and is the perfect place to take a refreshing break from the road. Grab a trail map at the centre and set out on the self-guided pond tour, where interpretive signage walks you through the local ecosystem and wildlife. The trails are flat, accessible, and genuinely pleasant.

Optional detour: Souris Swinging Bridge (30 min south): If you have the time and a taste for adventure, the town of Souris is home to the longest swinging suspension footbridge in Canada. Discover the 184-metre pedestrian bridge that sways gently over the Souris River. Completed in 2013, it reclaimed Canada's record title and is quite a thrilling walk. It'll add an hour or so to your day, but the photos are worth it.

Second Stop – Virden, MB – 3 hours from Winnipeg

Virden is the halfway point of your drive, which makes it the perfect excuse to stop the car and get a little fresh air. The Pioneer Home Museum here is well worth a wander. It's one of the oldest buildings in the region, and inside and you'll find vintage furnishings and local artifacts that paint a surprisingly vivid picture of what prairie settler life looked like back in the late 1800s.

Virden is also an oil town. The pump jacks visible across the surrounding fields are a reminder that this stretch of the Prairies runs on more than just wheat.

Third Stop – Moosomin, SK – 4 hours from Winnipeg

You've crossed the border and now it’s time to celebrate with lunch! The Red Barn in Moosomin is a classic Prairie roadside stop. It’s the kind of place with a menu that doesn't overthink things and portions that don’t disappoint. Make sure to try their famous fried chicken!

Fourth Stop – Grenfell, SK – 4.5 hours from Winnipeg

Grenfell is home to one of Saskatchewan's most distinctive public art projects, the Millennium Murals: a series of large-scale outdoor paintings scattered across the town that celebrate local history, Prairie landscape, and community identity. Each mural tells a different story, and together they turn a walk down Main Street into something genuinely memorable. It's a quick stop but a vivid one, the kind of small-town discovery that lingers in the memory long after you've driven on. Bring your camera!

Fifth Stop – Indian Head, SK – 5 hours from Winnipeg

There is no more important stop on this drive than the Indian Head Bakery. Full stop. This beloved local institution has been feeding travellers and residents alike with the kind of baking that makes you question every grocery store loaf you've ever bought. Whether it's fresh bread, pastries, or whatever they have behind the counter that day, get some! Actually, get more than you think you need. You will not regret it.

Pro tip: Indian Head is also worth a slow drive-through in its own right. The town has one of the most beautiful main streets in southern Saskatchewan, lined with mature elm trees that form a remarkable canopy.

Optional Scenic Route

Before you roll into Regina, take the scenic route through the Qu'Appelle Valley. This is one of Saskatchewan's most beautiful landscapes. Enjoy a stunning carved valley with lakes, rolling hills, and river flats that feel like a completely different province from the flat plains above.

Drop down into the valley, follow the winding road along the lakes, and let the landscape do what it does best. It adds maybe 30–40 minutes to your arrival time and is the perfect finale to a great drive.

Sixth Stop – Regina, SK – 6 hours from Winnipeg

Welcome to your final destination, Regina, Saskatchewan! Make sure to visit Wascana Centre, one of the largest urban parks in North America, and take in the gleaming dome of the Saskatchewan Legislative Building as you roll in.

While you’re in the park, stop by Bar Willow Eatery for a drink and a bite to eat on the patio. This is also the perfect place to watch the sunset over the lake. Enjoy! You’ve earned it.