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Feedback and help on New England Itinerary

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Hi,
I've seen some excellent advice on this forum which has been very helpful...

I am planning a trip at the end of September with some holes, as follows (and I live in NY).

Sun., Sep. 23--this is not a definite but I am thinking of leaving this day and driving through Lennox Mass (and maybe checking out Stockbridge), on my way to Southern Vermont.

I have Reservations on Monday and Tues. nights (9/24 and 9/25) at the Windham Hill Inn (I forget the town, but it's definitely southern Vermont).

I was planning on spending those days (Monday, Tues. and maybe Wed.) exploring the area, staying at Winham Hill as my base for my two nights, then on Wed. and Thurs. nights I have reservations at the Rabbit Hill Inn (in Lower Waterford, VT) which is considered in the Northeast Kingdom, but it is in the Littleton/Johnsbury, NH area (so I guess it's right near the border)...so I do plan on taking up someones suggestion on another post to check out the Littleton Diner (especially their hash!), and I saw it featured on the Food Network (I think) so it looks fun. Anyway, those two nights (wed. and thurs) and surrounding days are part of my explore the area days (so ideally, between the two inns, I will hopefully explore some of the cute towns, but haven't decided particulars yet). I'm going with my boyfriend, and we're both pretty active, so some hiking, maybe biking if time allows is in store...

Then, I have left the Fri. night open, and I don't know if I should explore more of New Hampshire, or spend the night in Boston...maybe check out Rockport, Mass. above Boston on the way...or should I be going to Portland instead, too many options!!...looking for advice on the Friday part....I can also always head to Providence... I have reservations on Sat. and Sun. nights in Newport at the Francis Malbone House. Monday at my lesiure I am driving back to Suburban NY, because I have a work event to attend on Tuesday, but them my vacation resumes after that (I may not plan anything after that point though because my boyfriend who is from Scotland may need to visit some family). My main concern was that originally I was trying to fit too much in, but think I am ok now, but probably don't have time to do a ton on Friday (originally I was going to try and include Marthas Vineyard AND Newport in my trip, but decided I was packing in too much with the ferry, and that it might be better to enjoy and explore Newport.

So, to recap, my reserved inn nights are:

Mon. night and Tues night - Winham Hill Inn in So. VT

Wed-Thur nights - Rabbitt Hill Inn N/E vermont near NH border


Sat/Sun nights in Newport

I have some flexibility on the front end, and Friday and no reservations for those two nights....does this sound like a good trip to people, are there any suggestions for the things I'm not sure about, or any must see spots? Should we be making sure we're checking out some of the covered bridges or any particular towns that would be within driving of where we are staying....

(My boyfriend and I are pretty active, and we're early 40s. I chose New England because I figured coming from Scottland, he'd really appreciate our beautiful autumns in the north east)

Looking forward to peoples comments and suggestions!!

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