Hills are often hateful to cyclists! I really quite like hills. The overall ride is just over 91,000 feet of climbing. The worst is done but the Green Mountains will be a bit hilly but nothing like the Rockies. It’s all in the mind. A really useful resouce for the Garmin files is Bike Route Toaster you can search the cities and download the appropriate Garmin file. I have not used, as I quite like the simple paper cue sheets.