My buddy Terry and I went to see the Jefferson Hill Climb by van last year, since it is a bit over 400 miles one way, and we had to be back the same day. We also attended the Triumph Come Home Rally with a bunch of other classic triple riders. Two days down and one long one coming back, but we thought the White Rose site was excellent for camping, and their banquet was great. We took home the longest ride trophy, which we gave to our buddy Dave, who loaned his Legend to Terry for the weekend as Terry's Honda 450 twin was having carb issues.
There were some nice roads and even nicer people at the event, and the camping was great. The one experience that I won't forget is that train engineer blowing the whistle when he went through at 1 in the morning. I had not noticed that the tracks were only about 50 yards from my tent, and when that train went through I just about dropped a load in my sleeping bag!
If any of you PA folks have the time for a more leisurely ride to Bennington, we used the Steel Steeds campground in PA:
http://www.steelsteedscamp.com/ (camp down by the river)
and the Little Pond Campground in NY:
http://www.dec.ny.gov/outdoor/24478.html (very nice and quiet)
The ride up through the Catskills was great for us, but unfortunately, the flooding last summer made a mess of much of the towns along our route, so I am not sure how many stores are back up and running?
Definitely check, but the route itself is a wonderful ride, with lots of great roads and very litle traffic on most of it. If anyone is interested, drop me a note and I can give you our route.