Want to do CDT Leadville to Steamboat in September 2017

I retire next week and plan on backpacking for my next career. I have mostly backpacked in the PNW but I was a rookie backpacker back in 1976-87 from Denver to Steamboat Springs. So I want to put together a trip from around Leadville on the CT/CDT to Steamboat. I have been raising an Australian Shepard, Brook, to be my companion and she will be fully tested by the time we hit Colorado. I typically average about 12 miles a day.  So I'm looking for advice: I will launch from Vail so what is a good trailhead to start out from? Any other advice about resupplies along the way that might be conducive to finding some good beer and be somewhat dog friendly communities would be great. GHSMITH76 is my social media name and my Blog is: The Adventure Continues