Hello and welcome to the RTA forums !

You really haven't told us much about your plans to be of much help, but that looks a lot for 2 weeks, especially if you have to return to Denver and your plans include a visit to Yellowstone as you mention 'Jackson'. Perhaps if you share more details of your plan then we can make suggestions. So yes, it's possible but whether or not you have time to make it as enjoyable as you like is debateable.