Passport Required
We woke up on Saturday morning with the idea of taking a day trip to Regina, Saskatchewan (SK), Canada. It’s about 180 miles one way, so we knew it would be a bit of a trek. With a later start than usual for a trip like this, we knew we’d be getting home late, but we couldn’t resist thinking, "You don’t get opportunities like this every day." We finally hit the road around 10 am, heading west out of Williston, ND on Highway 2. The morning air was a little brisk, around 57 degrees, but the forecast promised the temperatures would rise into the high 80s or low 90s. It was shaping up to be a perfect day for a ride.
After riding about 13 miles, we stopped to fill up the gas tank. My wife was feeling colder than expected, so she added another layer and grabbed her gloves. Once the bike was refueled and she was warmed up, we continued north on Highway 85 towards Fortuna, ND, and the Fortuna Port of Entry into Saskatchewan.
To enter Canada, a passport is required, so we were ready for that. The border crossing process can sometimes be a bit of a hassle depending on the agent, but this time it went smoothly. The border agent was friendly and let us know that this particular crossing closed at 5 pm CST. That was when we realized we'd need to return through a different crossing to get home. Luckily, we had two options: one to the west, which was open until midnight, and another to the east that was open 24 hours. With that sorted out, we were ready to continue our journey.
I quickly switched the bike to metric displays so I could keep track of the speed limits, and we were headed north on Canada Highway 35. To be honest, this road isn't the most motorcycle-friendly—it's a patchwork of asphalt and heavily traveled by oilfield trucks. But, like always, we decided to power through it. Thankfully, the first rough section only lasted about 27 miles before we hit some newer pavement.
Another 31 miles later, we reached Weyburn, SK, where the road conditions deteriorated again. It wasn't as bad as the first stretch, but it still wasn’t the best ride. If you’re looking for scenic views beyond endless farmland, this route won’t be your favorite. Both sides of the road were lined with fields, and harvest season was in full swing—along with my allergies! Tribune, SK, was a small town with little to offer, while Weyburn, SK, was a bit larger and had more traffic, making the ride a little more congested.
In Weyburn, you have the option to take Highway 39 northwest toward Connie and then head north into Regina, SK. However, we decided to stick to our original route and continued north on Highway 39 for about 31 miles. Once again, it was mostly farms and ongoing harvesting, with not much to break up the landscape. After the 31 miles, we reached the intersection of Highway 35 and 33. We took a right turn and headed northwest on Highway 33 toward Regina.
Even though the road was still surrounded by farmland, we started to see more motorcycles out on the road, which made the ride a bit more lively. I should mention that the speed limits in Canada are a bit more conservative than what we’re used to. On the two-lane highways, the limit is 100 kph (about 62 mph), and I made sure to stick to it. I wasn’t sure about the fines for speeding, and honestly, being an American on unfamiliar roads, I didn’t want to attract any unwanted attention. Once we hit the Canadian Interstates, the speed limit increased to 110 kph (about 68 mph), which felt a little more familiar but still required some adjustment.
For the next 47 miles to Regina, we saw a ton of motorcycles on the road. What was interesting, though, was that they were always in small groups. We rarely passed just a single biker, and as far as we could tell, there wasn’t any sort of official group ride going on—just groups of friends out enjoying the day. The closer we got to Regina, the more bikes we saw, which made it feel like we weren’t the only ones on the road. It was nice, but I couldn’t help but notice the US plates on our bike getting a few extra stares. I’m sure some people were curious about what we were doing up there, but honestly, I didn’t care much. I wasn’t there to impress anyone.
Our first stop in Regina was at Prairie Harley Davidson, a small dealership with some of the nicest staff we’ve encountered during our travels in Canada. After picking up a couple of poker chips and a new t-shirt for my wife, it was time to find some food. We decided to head to a mall, knowing we would both find something we liked and have a chance to relax after the ride.
The Cornwall Centre is Regina’s "premier" shopping center, so off we went. Regina is a pretty large city, and the traffic was non-stop everywhere we turned. By this point, it had warmed up quite a bit, and sitting at each stoplight on the bike was starting to get pretty hot. The mall is located in downtown Regina, and the area surrounding it felt a little sketchy—definitely not a place I’d want to be after dark.
After circling the block a couple of times, we finally figured out how to get into the parking garage, and we managed to snag a front-row spot—always a bonus. Now, for most married guys, a mall trip is usually code for “the wife is going shopping,” so I made sure to throw an extra bag on the bike just in case she got carried away. Three hours later, she was ready to leave. As it turned out, we were only walking away with a sweater—so I’d call that a win!
It was getting late, so it was time to start heading back home. But with my wife, it’s never that simple—she has this thing for checking out new grocery stores. So, we made a quick detour to Sobey’s, a Canadian supermarket, so she could browse around. After about 30 minutes of her exploring, we filled up the bike and got back on the road.
By this time, it was after 5 p.m. CST, and we realized the Fortuna Port of Entry was closed, so we decided to cross through the Regway Port of Entry, which takes us into Plentywood, MT. This detour added about 20 extra miles to our trip, but we knew that ahead of time, so no big deal. We jumped onto Highway 6 out of Regina and headed south toward Montana.
The next 110 miles were pretty uneventful—just miles of open road with little to see except farms and an occasional farmhouse, which were few and far between. There was only one small town on the route, but you don’t even really go through it. Make sure your gas tank is full because there aren’t many places to stop for fuel along the way.
Finally, we reached the Regway Port of Entry. We breezed right through and were back in the U.S., with another adventure under our belts.
From here, I know these roads like the back of my hand. We’re now on MT Highway 16, and the speed limit is 65 mph, but we’ll kick it up to 75 mph and make a run for it. The sun is setting, and we’ll be riding into the night, so we need to make the most of what daylight we have left and get as far as we can before it gets dark.
We made a quick stop in Plentywood to hydrate and grab a snack. With half a tank of gas, I wasn’t worried about making it home. We had a couple of options from Plentywood back to Williston, but we stuck with Highway 16 until Culbertson, MT. From there, we turned east onto Highway 2. This is the home stretch—just 50 miles to go.
We kicked it back up to 75 mph and made good time, but as it got darker, the wildlife started coming out, so we slowed down a bit to be safer. By the time we pulled into the driveway at 9:30 p.m. CST, we were finally home. It was a long day, but a good one, with plenty of miles under the tires and memories made along the way.
We ended up crushing a little more than 415 miles for the day. The ride itself was smooth and uneventful—just the kind of ride you hope for. My wife kept the spending to a minimum, which is always a win, but three-plus hours of shopping were a bit draining. Would I do it again? Absolutely! We had a fantastic time, and next time, maybe we can check out Moose Jaw, SK.
If there are any Canadians out there who want to show us around on two wheels, hit us up! I’d love to see what kind of riding Canada has to offer. Until next time, it’s just the open road and the freedom that comes with it.
