What will you be riding? That makes a HUGE difference.
Engineer's between Lake City and Silverton is fun. The East side is not too challenging, the West side is tougher. Cinnamon Pass is just South of Engineer pass, starting at Animas Forks and running East to Lake San Cristobal on Hwy 149 just South of Lake City. I did not get to do Cinnamon personally as my day was cut short and I headed back to the hotel. The other guys went ahead without and loved it. By the way, if you happen to be in Lake City around time to eat, I HIGHLY recommend Poker Alice's. It has always been a favorite of everyone when I have led large group rides in that area.
I really liked Scotch Creek Rd. It starts just South of Rico on Hwy 145 and runs over the mountains to Hermosa Park Rd. which comes out on US 550 just South of Silverton. The first part was pretty rough, but once we got past that, it was not bad and the scenery was awesome. The Scotch Creek side of the mountain does not appear to get that much traffic. We had the whole place to ourselves. The East side has more traffic, but even then it was very light.
We did another loop that was West of Telluride. This is the loop where I flipped the GS. Parts of it were technical and other parts just fantastic solitude and scenery. It starts on Hwy 145 just Northwest of Sawpit (before you reach Hwy62). I think it is 57 P or Fall Creek Rd. We ran it South to G49 Rd, which cuts West a while and then South around a mountain. That eventually hit CR 52 and cut back to the East to CR 38 (Dunton Rd.). From there, we cut East to Hwy 145 just North of Rico.
Owl Creek Pass is East of Ridgeway and you will eventually come out on US 50. Take CR 8 East from US 550 (just North of Ridgeway). The more technical stuff will be on the West side of the mountains. At the top, you reach CR 860 and start down the East side, heading North to CR 858 at Silver Jack Reservoir. CR 858 runs along the Cimmaron River up to US 50 near Black Canyon of the Gunnison.
There are miles and miles of spectacular roads in that area. Most could be done on a V-Strom 650, but I would HIGHLY recommend a good bash plate and maybe side guards! I did it on the R1150GS. It would have been MUCH more fun on one of the 650's (KLR, DR, XR, XRL, etc,...) with knobbies. The big thing is that there is very little traffic in some of these areas and it they can be quite remote. I don't know that I would ride any of it alone.