I live in Weatherford and I like going through Santa Fe and then up to Pagosa Springs. From there South Fork is a short drive but you do have to contend with Wolf Creek Pass.
I've always done the trip in my SUV without a TT. This year will be my first time to pull a TT through Colorado, but I bought a new tow vehicle for the job.
North of Santa Fe are several casinos that would make a good overnight spot. I've always made it all the way into Pagosa Springs with plenty of time to spare, but like I said, I've never done the trip towing anything.