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New England - late summer or fall?

My friend and I are planning a trip this year, part nostalgia (grew up near Hartford in the 60's/early 70's), part family (short visit near Wolfboro NH) and mostly sightseeing. We are planning about 10 days to include: Fly into Bradley and quick drive around to see the old neighborhoods, overnights in Mystic, Newport RI area, maybe Rockport/ Gloucester, Kennebunkport, over to Wolfboro for a day or two, back to the coast in Maine and up to Bar Harbor for 2 or 3 nights. Fly out of Bangor.

Two questions.
1. Dates are flexible. Although seeing fall foliage again would be nice (having lived in Fla for the past 50 years) , I'm afraid it will be too crowded / expensive. I am perfectly fine with going in early to mid September as I think late summer weather will be lovely (and MUCH cooler still than Florida) and skipping leaf peeping season madness. Any thoughts on this topic?
2. Any thoughts on the rough itinerary above? Anything that I'm missing that really needs to be included? Any suggestions are welcome as to where to stay, must do's (whale watching etc). We are late 60's/early 70's. Fairly fit but no long involved hikes. And, of course, any favorite restaurant suggestions are welcome! I'd like to avoid chain hotels - inns and b&b's that don't break the budget are perfect. However if there is a splurge that you'd recommend to stay, that's doable too.

Thank you so much!

Posted by
62 posts

I vacationed in Newport a few years ago and loved it. Lots to do. Mansions, tennis HOF, car museum, cliff walk. You could also spend a day on Block Island and moped around. Stayed at the Brenton Hotel which I highly recommend, but booked way in advance and got a great price.

Posted by
3299 posts

That sounds like a perfect itinerary to me!

Posted by
495 posts

The colors are worth any crowds! We were coastal Maine last yr. Perfect timing for color…early to mid Oct. We have no regrets. Just get going early morning! Bar Harbor too expensive…so we got a BnB near there. Get reserved asap! Go on booking.com….