Why in the hell are your driving?! Jeez man, by the time you pay for all the gas and meals, you've probably come damn close to buying a round trip ticket. My fiance is from MD and I'm from NC and when we head back, we can usually find tickets for $250 or less. Plus, driving that is just a killer. You can do it in one haul, but it's 20+ hours to Denver (about 22 to my home in NC and 23 to her's in MD). You'll waste a day out here just recovering. If you stay the night somewhere, that's just more money that could've gone toward a plane ticket.
And oh yeah, for the type of riding you described, Vail is a great option.