I have been doing the Mickelson trail every for the last 10 years. I recommend going in late September or early October as the weather is much cooler and the trees have started turning. As a general rule, the Mickelson Trail doesn't have a lot of towns along the trail. We always make our base of operations in Hill City, SD. Hill City is a nice central point along the trail and with several hotels. There are a few shuttle services available in the Hill City area which makes it easier to get around. We typically take a shuttle from Hill City to Deadwood. and start at the Sugarloaf trailhead which makes for a nice 42 mile ride back to HiIl City. On day 2 we usually ride from Hill City to Custer, SD and back.