You don't have to go that whole loop of course. It's easy to break up, since you can turn back to Free Union from a lot of places. (that road is about the same up or back). Taking Markwood instead of Simmons Gap cuts out some distance too. I've done a 25 mile version, a 34 mile version, and a 47 mile version of those roads (minus the dirt ones).

Mudhouse is probably the best coffee shop. Go to the one on the downtown mall. I think it's at the end with the theater. Greenberry's used to be good (there's one in the Barracks Rd shopping center--Garth Rd on the map turns into Barracks) but lately it's been so so.

You can find awesome pizza at Christian's (also on the mall), and great bagles at Bodos (one on the "Corner" at UVA, one on 29 near Barracks).

Let me know if you have any other questions.