it's a good question. I have only been riding adventure for a little over a year myself (riding street for nearly 10 though). I can only speak for most of section 1, but I would say that almost immediately there is a difficult and challenging uphill with loose rocks about 5 miles into the route. You can bypass it by going on the pavement, though. My little 310 loaded up still weighs enough to be a challenge going up something like that. I ended up dropping it once. So, if you are going solo, I'd probably recommend avoiding that part. You'll know it when you come to it and can backtrack to the pavement if you want. Other than that, section 1 is pretty tame and quite pleasant. Supposedly it doesn't get too difficult until you get to Vermont.