A few years ago, some friends and I made a similar road trip, Toronto to Edmonton. We went via the States for the (then) cheaper gas. We traveled as follows:
Day 1: Toronto ON - Sarnia ON - Flint MI (overnight stay after 8 hours driving).
Day 2 and 3: Flint - Mackinaw Straits bridge - Marquette - Ironwood MI- Superior WI - Duluth MN - Bemidji - Grand Forks ND - Minot ND (overnight stay after 36 hours taking turns driving)
Day 4: Minot ND - Portal ND - Estevan SK - Weyburn - Regina - Rosetown - Alsask SK/AB - Hanna - Red Deer - destination just south of Edmonton (arriving there at 11 PM).
Total distance was ~3500 km in only four days, but that was really pushing it. It was only possible because we had six people and two cars and were able to rotate people among the tasks, with one person driving, one person as copilot (reading maps, talking to keep the driver awake, providing coffee, etc), and the third person sleeping in the back. Shifts were three or four hours. Even so, by the time we got to Minot, we were in this weird giddy hyperactive state of tiredness that I can only describe as being drunk on exhaustion.
If you’re going to do it with only two people driving, you will need more time. <rereads OP> Oh. One person driving. Make that lots more time. At a guess, with eight-hour driving days and not pushing it, a week.
Make sure your car is in good shape. Do not drive that far with a problem car. Especially do not drive that far with an old Buick that drinks about a litre of oil a day and gives off a smoke cloud like an escaping squid when stressed. (More on that later.)
The trip was my first experience of the prairies. Amazing. My mom was born near Weyburn, and she always used to talk about the sky and the land and how unforgettably beautiful it was, and I never understood till then. Driving through the prairies was interesting. At times I felt like my eyes were going to be sucked out through the windshield and into the point on the horizon where the road disappeared…
One thing about driving through on US 2 ( a two-lane highway) though: that 55-mile-per-hour limit really sucks out west. You get the feeling that the wheels are turning but nothing’s moving. If you’re using the Interstates, you should make better time.
On the way back, we used a slightly different route. In Alberta, we’d gone down to Calgary, so we headed back along the Trans-Caanda, but then turned right just after Medicine Hat and took a minor road south. This was an eye-opener. We passed through Cypress Hills Provinvial Park: beautiful forested slopes rising from the prairie. At the top I was expecting a slop down, but that never appeared. We continued south. The road became narrowwer and narrower, and began to be rough and overgrown. Then we came to a sign: No services or residences next 137 km :eek: We continued. After a while the road swept around a curve and we were at the US border.
The border was a fence in the middle of nowhere. The Canadian border post was four pretty green-roofed white wooden buildings in a treed enclosure. The US border post looked like an old gas station, with two 1950s bungalows nearby, jurtting baldly up from the prairie. After finally being admitted by the customs agent (a story in itself), we continued south. There were access roads leading to fenced-in military enclosures. We found out later that’s where they kept (some of) the ICBMs… :eek: Eventually, we got to Havre, MN, and were back on US2, heading east.
When we got to Glasgow, MN, we stayed the night. In the morning the car wouldn’t start. We needed emergency repairs (a new starter motor or alternator or something). Moral: make sure you have an analogue cellphone with roaming agreements, and an up-to-date subscription to AAA Roadside Assistance. We were lucky: the motel we were in was across the street from a UAP/Napa Auto Parts centre and that saved our butts.
Interesting Roadside Attractions Dep’t
We were in such a hurry that we didn’t stop at much, but we did pass the Geographical Center of North America, located near Rugby ND, east of Minot. Yes, that’s me in the linked picture, and yes, the monument is across the road from the Hub Motel. 
Ginger, it looks like your route will be south or our route until you get to Minot.
I’m happy to see that you’ll be passing Madison WI. It’s a beautiful state capital, located between two lakes–very nice in the summer. The State Capitol building is at the centre of town, and all streets converge at it. Madison is apparently known for open-mindedness and tolerance; I passed through it on the way to the International Pagan Spirit Gathering which took place near Madison one year.
And it seems there’s quite a contingent on Dopers from the area. 