Historic Black to Yellow Trail At a Glance Distance: 312 miles Trip Length: 2 days Start/Stop: Brookings or Wall Sunflowers, small towns and authentic little houses on the prairie are highlights of this drive on one of America’s oldest highways. In the early 1900s, US Highway 14 was promoted as the most direct route between Chicago and Yellowstone National Park; as it passed through South Dakota’s Black Hills, the road was branded the “Black to Yellow Trail” — and many of its historical charms remain today. 32 // #HiFromSD Ingalls Homestead