The great Canadian prairie road trip: Calgary-Saskatoon-Regina-Winnipeg

This road trip had its genesis in idle travel fantasy chat, as so many journeys do. A few months ago my friend Melissa and I discussed how much we wanted to do a road trip together over the summer, and we cranked out a number of ambitious itineraries. The craziest of all involved Melissa driving 18 hours by herself from Colorado to Alberta to pick me up prior to an eastward run across Canada. Perhaps it’s best, all things considered, that this particular itinerary did not work out.

Time and other constraints meant that we had to curtail our ambition just a bit. We settled on a four-night Calgary-Winnipeg itinerary, with stops in Drumheller, Saskatoon, Moose Jaw, Regina, Brandon, and Portage La Prairie, a distance of 1486 kilometers or 912 miles.

Sounds great, right? Not so fast, cowboy. It turns out to be difficult to orchestrate a Canadian prairie road trip with a rental car. One-way car rentals are scarce in Canada. In fact, we were unable to find a single car rental company that would let us pick a car up in Calgary and drive it to Winnipeg.

After exhausting online booking site options, I turned to Twitter. The ever-generous travel writer Eva Holland suggested we take a look at Rent-A-Wreck. We did, and were disappointed to discover that the outfit doesn’t operate in Saskatchewan and Manitoba. The rather less literally helpful Grant Martin suggested that we purchase the PaceSaver Plus III Electric Scooter that he so kindly found on Craigslist.

We even looked into the possibility of renting a U-Haul, rejecting that option because it was too expensive. Thinking that there might have been some secret I’d missed, I even checked in with the very helpful logistics team at Travel Alberta. Again, no dice.

Disaster! How would we ever consummate our Canadian prairie road trip?
Fairly easily, as it turns out. Once we started scrambling everything fell into place quickly. We found a one-way Winnipeg-bound car rental originating in Saskatoon. And then we found a cheap one-way fare on WestJet between Calgary and Saskatoon. (A silver lining was already emerging, as I’ve wanted to fly WestJet for some time.)

Cutting out the first day on the road means that we’ll miss some beautiful territory across Alberta and Saskatchewan, Drumheller in particular. In place of that first day on the road, we’ll spend a morning exploring Calgary and a long afternoon and evening in Saskatoon. With the replacement of Calgary by Saskatoon as the point of our road trip’s origination, our road trip will shrink to 873 km, or 542 miles. Here’s the itinerary breakdown. Day 1: Nighttime arrival in Calgary. Day 2: Calgary and Saskatoon. Day 3: Saskatoon to Regina by way of Moose Jaw by car. Day 4: Regina to Winnipeg by way of Brandon and Portage La Prairie by car.

In addition to my posts here, I’ll be tweeting about my Canadian prairie road trip with the hashtag #cdnprairieroadtrip for the next few days. Our road trip will deliver me to Winnipeg, where I’ll spend the following five nights reacquainting myself with the Manitoban metropolis.

Read the entire road trip series here.

Some media support for this road trip was provided by Travel Alberta and Tourism Saskatchewan. All opinions belong to the author.

(Image: Flickr / Space Ritual)