Great trip route - you'll have a lot of fun. You will be in the car quite a bit (eg, the portions across northern New England - there are no flat, straight lines from Woodstock to Stowe/Burlington/Mt. Washington/Portland) but it will be great scenery and you have great destinations.
Are you looking for specific recommendations - types of activities, foods etc?
Sounds like you like high end food experiences - Duckfat is the best restaurant in Portland IMO. There are too many to name in Boston but my wife's current favorite is Contessa at The Newbury Hotel. Curve ball for your New York stop: if you like vegetarian, a place called Dirt Candy on the Lower East Side is a new Michelin star. I couldn't get in last year; you need to make a reservation exactly 30 days in advance or be willing to wait for a walk-in table.
Enjoy....