Wear Compression shorts or something similar. Definitely avoid cotton underwear. +1 on the spot tracker. I've carried one for past 4. Never had to use it, but nice to know its there. ( I use the tracking feature every ride.) If you can't borrow one, Pauly's advice about texting someone your location occasionally is a great idea. Otherwise, stay hydrated, and stop every few hours to stretch off the bike. On routes, 33 from Elkins to Harrisonburg is a blast. I was just on it Memorial Day weekend. Enjoy the ride.