The ancient Flambeau Trail was an important commerce route for Native Americans, voyagers, and explorers traveling between settlements at LaPointe on Madeline Island and Lac du Flambeau ninety miles to the south. Until railroads came in the late 1880’s, it provided the only transportation link between the Lake Superior watershed to the north and the Mississippi watershed to the south. By the time travelers reached this crossing, they had already portaged twenty-seven miles uphill from Lake Superior and over the Penokee Mountain Range, with eighteen more miles of overland travel remaining to cross the Continental Divide. At Long Lake, navigable waters offered easier canoe travel to points south. The trail was narrow and filled with overturned trees, muskeg, and thickets, and completing the portage and paddle to Lac du Flambeau took between two and a half and seven days depending on trail conditions, the load carried, and the travelers’ motivation. It was considered among the most difficult portages in the old Northwest Territories.