Starting in Duluth:
See: The Lift Bridge (just cuz)
Eat: At Sara’s Table
Tour: Glensheen Mansion (ask about the murders now that they can talk about 'em)
Leaving Duluth-make sure to take the scenic route or else you’ll miss part of the lake. Pop in some Bob Dylan and enjoy the ride.
Next big town is Two Harbors and the appearance of Betty’s Pies. Grab a slice of pie (but ignore the rest of the menu.) This is the last major grocery store until Grand Marais too. The city also has a Pamida, and is the last of the kind of store until you get into Canada.
Leaving Two Harbors, there are 2 state parks that need a visitin’. Gooseberry (for the waterfalls) and Split Rock (for the lighthouse). Both of these have some great hiking trails too.
Next, take an Alpine Slide ride on Lutsen Mountain. Yes, even adults have fun doing this. Even if it is to take the chair lift in the summer to get great views of the area.
The rest of the drive is quite scenic and the next place to stop is Grand Marais, MN. This little town just feels right.:
Eat: Naniboujou Lodge for brunch and to see the Native American influence
Snack: World’s Best Donuts
Get a bumper sticker: Sven and Ole’s Pizza.
See: The lighthouse, the island around the lighthouse too
Do: North House Folk School. This place has amazing classes on how to build chairs or boats or knit et al. They also offer great sunset cruises. Check 'em out.
Before you leave Minnesota, pop into one last state park, Judge CR Magney. This is a gorgeous area to hike in. The topography is so atypical for Minnesota and will be the last of it for a while before entering into more of the plains area into Canada.
Grand Portage has shuttles out to Isle Royale (no cars allowed). It also has a fort which is worth exploring. Also, fill up on gas before leaving the country. It’s cheaper here. (It’s also worth noting since you’re coming from Madison that MN gas is cheaper than WI gas).
The next big city is Thunder Bay and while it’s cool to be in Canada, it’s just kind of…well, a shit hole. It’s not horrible, it’s just very working class and after the beauty of Minnesota’s North Shore, it’s kind of a let down.
See: The statute of the guy who was going to run all the way across Canada but only made it to Thunder Bay
Eat: Tim Horton’s (natch)
Hike: Sleeping Giant Park (There are some great views here).