Join Date: Apr 2007
Location: Northern VA
Bikes: 2008 Trek Madone 5.5, 2009 Cervelo R3SL tdf edition, Cervelo R5 with Di2
There are not too many "long" climbs, and they're not horrendously steep. Longest ones I can think of are right out of Front Royal, Hogback (both ways), up to Pinnacles, and maybe a couple others further south. Just gear down and spin is the best advice.
There's a deserted HOJOs at the Waynesboro end where you can park, but there are no services there. To get water and other supplies you'll need to ride down to Waynesboro another couple of miles.
The main issue of doing it all in one direction is how to get back to the other end. Apparently some of the local bike stores can hook you up with a driver to haul you back to the start.
What I've done a couple of times is start in the middle at Big Meadows, and do out-and-backs over two days (first day south and back, and second day north and back or vice versa.)
p.s. I see we live in the same town. Howdy neighbor!