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PA, ME, VT, NH road trip in October - advice needed

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I am trying to figure out the best way to route this trip and thought I would throw it out there for some expert opinions. I know I have a lot more research to do. We are from Chicago and have two weddings to attend out east. One is 10/13, Columbus Day weekend, in Philadelphia, and the second is 10/19 in Littleton, NH. We figure we will stay out east for the week and explore. We would like to spend a few days near Acadia National Park. We would also like to see fall color, although I know we are kind of at the end of the season for that, but that's fine. While my husband is a big hiker, I only like easy to moderate hikes. I was thinking maybe we could fit in Green Mountains in Vermont, White Mountains in NH, parts of the Appalachian trail? Should we fly from Philadelphia to Maine and then work our way back? I just can't seem to wrap my head around the best way to do this. I know we need to book hotels asap as it's a popular time to go. Any help would be greatly appreciated to get me started.

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