My rating: 4/10
The Webster Pass trail commences basically at the start of the ascent up to Kenosha Pass (going westbound) and ends up in Montezuma to the north. The trail itself is quite easy and really only has two challenges. The first one being the torn up bridge that spans, or used to span, and eroded and muddy part of the trail in Handcart Gulch. If it is wet, it could be a considerable challenge getting up the ~1' ledge. The other aspect of the bridge is the fact that there are 5" nail spikes sticking up and going in each direction. Tire placement could be critical. If this area is dry, it should pose no problem. This was in the summer of 2003, so we'll see if it gets repaired at all for the seasons to follow.
The only other moderate aspect of the trail is the extremely narrow shelf road just below the pass summit (12,096') on the south side. In fact, it is the narrowest shelf road I have ever been on, and that covers the other notable ones in Colorado. It is the only shelf where I have felt a little nervous driving it. I'm glad I have a narrow rig to be sure! I usually love shelf roads, but this one was a little different when I first drove it! I can only imagine what passengers see and think about when going up here!
The area is very scenic at the top and the road itself is just flat dirt for the duration. The pictures below are from a couple of different trips up.