[kbroderick]

If you want to make 100 more interesting, you could do a multi-gap ride (start up 100N, cruise across 73 through Brandon Gap to 53N, 125E to 100N, 100N to Lincoln Gap Rd, 116N to 17E back to 100)...that would mean crossing the Green Mountains four times. It would also involve some interesting road surfaces (as noted in another thread, 125 is kinda interesting at the moment, more so eastbound than westbound; Lincoln Gap Rd has a gravel section, I believe) and a lot of twisties. If you really wanted to get your money's worth, continue 100N to 108 through Smuggler's Notch and loop back via 15 to either 12 or 14 south (or continue into NH), depending on where you want to end up.

Basically, if you want to avoid boring, look at where the roads cross over the Green Mountains...very few of those roads are boring, and most are scenic.