So much to do......so little time, as the saying goes.
Ok let's break this down one step at a time. So your flight into Boston arrives a bit earlier. That's a good thing. As long as you are not too tired to drive for three hours, you could head straight up to the White Mountains of NH and get a room somewhere up there for Thursday Sept 28th.
Friday Sept 29th: Spend the day exploring the White Mountains. Go up to the NEK late day and check into one of the places I recommended. The Comfort Inn that CT recommended is really nice, but I also think it's pricey. That's why I didn't recommend it. But if you can afford it, it is a nice place.
Saturday Sept. 30th........One of our members (From the NEK) spent a great deal of time a few years ago mapping out a scenic driving route that I think you should follow. http://www.scenesofvermont.com/phpbb2/viewtopic.php?f=1&t=3532&start=15
Titled "Scenic Driving Route Through NEK Central. Follow this route. Many people have followed it and have really enjoyed it.
[url]Google Directions without Wheeler Mtn Rd but with all optional offshoots (May Pond, Lake Willoughby South Beach, Island Pond, Burke Mtn Toll Road): https://goo.gl/maps/C54KRpQ1Ab82
It's a full day and gives you lots to see.
Sunday October 1st: Drive through Hazen's Notch from Lowell to Montgomery. Drive up Hill West Rd in Montgomery for some pretty spectacular views. Go to the Creamery Covered Bridge located on Creamery Bridge Road. Scramble down to the bottom of the bridge to see a waterfall flowing under the bridge. (It's not too difficult but use your best judgement with your two year old) Visit Jay Peak ski area and ride the gondola to the top for amazing views.
Monday October 2nd:
You have a choice to either stay at your lodging in the NEK and if you do you should go through the Groton State Forest which has lots of places to stop and photograph, visit the village of Peacham, go to a beautiful farm called Hillside Acres Farm in Barnet (beautiful to photograph from the road but you can't physically visit the farm) and explore the backroads n the Peacham/Groton area.
Or.........................you could head to Stowe and explore the Stowe area (others can chime in on where to go in Stowe) and put up at a different hotel in the Stowe area that evening.
Or.................you can head to the killington area and MMVT can recommend some pretty incredible places for you to see and photograph in that area. She could also recommend lodging for you as well. Killington area would have great color at that time due to the higher elevation.
Tuesday Oct 3rd......depends on which location you decide to stay at and then meander back to Boston from there.
If you decide to stay in the NEK the entire time there's other places you can visit that I can recommend but if you want to explore a different area of the state that will have good color, then decide where you want to go and we can help you from there.
It's your decision but you need to decide NOW.
One more recommendation.........and I'm NOT recommending this because I'm one of the authors
but I am honestly recommending it because I think it's a valuable thing to have and it will help you immensly........THIS WEEK the Ebook that I co-authored with Andy Richards is going to be available to purchase through Amazon.com, Kobo, Barnes and Noble and all of the other popular sellers. I highly recommend you purchase this Ebook. It contains specific locations, directions on how to get there, where to park, best time of day to shoot, and most locations contain gps coordinates. There are sample photos that you can see from each location.
Book is titled "Photographing Vermont's all Foliage" Where To Find The Iconic Shots 2nd edition.
Andy will post as soon as the book is available to purchase here on the forum as soon as it's approved from the publisher. Should be any day now.