I"d probably pop a few blood vessels in my head if I went all over the east coast on a steezy trip and got stuck having to chill on Blues with a gaper. I bet he wants to take a bunch of breaks during the day too. If you absolutely HAVE to take this guy, make sure you get some alone time during the day. Send him off so you can get the good stuff and meet up with him later on.
My advice, Hit up Stratton, then go North a little bit (You're already most of the way there right?). Stowe is amazing, but your friend would probably kill himself on the blues there plus its at least 2 to 3 hours north of stratton. Killington is only 30 miles north of Stratton, you can actually see Stratton from Skye Peak at Killy. That might not be a terrible idea.