This ancient trail extended from the Yellowstone River past this point to the Wood Mountains in southwestern Saskatchewan. For generations, Sioux and Assiniboine Indians used it to pursue buffalo and to trade with Canadian tribes west of the Great Lakes. After the Battle of the Little Bighorn, Sitting Bull and his Hunkpapa followers often traveled the trail while refusing to surrender to the U.S. Army, and in July 1881 he rode it for the last time to Fort Buford, where he finally surrendered. In the late 1880s, cattlemen drove longhorns over the trail into northeastern Montana. By the second decade of the 20th century, hundreds of homesteaders had settled this region seeking their own piece of the American dream on the windswept plains of northeastern Montana; although many did not achieve their ambitions, they left an indelible mark on the landscape and culture, and during the height of the homestead boom in the 1910s Scobey was the largest primary shipping point of grain in the world.