Havn't been to Watkin's Glen yet, but I know PDA has a couple of trips a year to Pocono Lawn... They're usually $300 a trip, and for the most part are "safe".
I know they sometimes go to Watkin's Glen, but I havn't researched the info yet...
I've been to Watkins. but not with my truck. The Ferrari club has an event there every year. The track is very hard on brakes, and there's not much to do around there entertainment wise. If you do go, I would suggest a trip to the Corning glass museum, especially if the wife's along.