For about 5 years, I've been hoping to attempt this route. I attempted this on a sunny, breezy fall day. I drove up from Duluth later than expected and started from the beach in Grand Marais after dropping my bike at the Eagle Mountain Trailhead. I took 2 partial flasks in a running vest with a little water and mostly a high-carb mix. I did not bring enough water on the run. I also regret not bringing more water, clothes & lights for my bike ride back into town.
I took the same route as Tim and put the GPX into my watch as a safety net even though I've lived in the area. The route is a mix of gradual climbing with a couple steeper parts. There are several miles in the middle of the route that are essentially flat. The last 3-3.5 mi from the Eagle Mountain TH to the top are moderately technical and eventually become steeper. There is potential for a lot more time to be cut down from this route, especially from those with a bit more running economy that can clock 5:15-30 miles on the flatter sections.