I can give you some details once your plans are more set. I did most of the trail as part of a loop tour in the Black Hills from/to Rapid City. Did a little bit into Deadwood the first day heading north and then picked up the trail heading south at the Englewood trail head after riding up Spearfish Canyon to Cheyenne Crossing from Spearfish, which I highly recommend if you don't mind climbing. (Not to sound snobby, but the town of Spearfish was a "breath of fresh air," and it has the nicest municipal campground I have ever experienced.) Stayed in Hill City the first night on the trail and then made it Edgemont the following day.