Here's the route I took pulling a 40' FW. My overall length with tow vehicle was 55': I-25N -> Cheyenne, just north of Cheyenne pick up US-85 North to Mule Creek Junction, WY, east on US-18 to Hot Springs, SD (taking US-18 Bypass around Hot Springs, finally north on SD-79 to Rapid City. That was 5 years ago and the only hill of note was coming down into Hot Springs. Not too bad. If you want to avoid the southern edge of the Black Hills (Hot Springs), you can go east on US-20 at Lusk, WY and pick up US-385 north just west of Chadron, NE. Finally, pick up SD-79 to Rapid City. If you get into Hot Springs, you missed SD-79 to Rapid City. Hope this helps.