My favorite road in New England is Rte. 17 in VT. You can pick it up from the NY border and it connects to rte 100, another very good road, it puts you pretty close to Middlebury. The best part of 17 is through Camel Hump Park, if you like tight, twisty roads it doesn't get better than this in New England. VT, NH, and western MA is all pretty good. You may want to take rte 112 across NH to Mount Washington, it's pretty good. I say pretty good because I spent a week in your neck of the woods, VA, WV, NC, TN, Deals Gap, and the roads were spectacular, nothing like them up here. Also your roads are so smooth, we have harsh winters that beats things up. As far as what I wear, I always pack more clothes than I think I'll need, and 40% of the time I use it. Temperatures change hourly and with elevation. My buddy has an Olympia AST (ATS?) three season jacket that he wears all year. Have a great trip!
2009 Wee Strom ABS (current)
1987 Harley FXR Low Rider Sport (current - with 206K miles)
2009 Aprilia Mana 850, 2006 SV650, 1984 Yamaha Virago 1000 (all sold)
Silver Strom Club Member #11
Wee Farkles: Russell Day Long Seat, Madstad with Moose Adventure Shield +4'', SWMotech Centerstand, 1'' up & back bar risers, Givi XS308 Tankbag, Aprilia mirrors, Framesliders, Fenda Extenda, Elka Shock.