The October crowds start now. Many of us feel that Salem has sold its soul for money. The whole economy depends on the tragic killing of individuals who never practiced witchcraft. The Bewitched statue, where so many tourists take selfies, is particularly obscene. The site of the 1692 witch scare was actually Danvers, where the Liberty Tree Mall now stands. Sorry, strong feelings since I have to be there a lot. The Peabody Essex museum and old houses are interesting. The crowds are at the Witch Museum and so on. Marblehead, Gloucester and Rockport are all good plces to visit. Only Marblehead doesnât get crowded though.
Ssshhh. One of our favorite things to do is picnic at Chandler Hovey Park at the tip of the neck and watch the sailboats glide in and out of the yacht club. 
Weâve had the park to ourselves a few times. Donât mess this up for us. 
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Concord has the Old North Bridge (and occasional visits to the site of various reenacters), Walden Pond, Alcott House, Concord Museum, Thoreau and Emerson sites, etcâŠ
Mooncusser is one of the best restaurants in Boston. Adventurous and well-executed â great chef. I didnât know that the same folks also own 80 Thoreau in Concord. It seems to me like well-executed, expensive comfort food. Not in the same class as Mooncusser.
In the Concord area, I tend to eat at the ethnic restaurants in Waltham and to a lesser extent Maynard.
I also think that visiting Harvard or MIT is usually fun for folks.
Iâd skip Salem (except for the Peabody Essex Museum, which is excellent). I used to have a company with its office there and it was already pretty touristy. Iâd opt for Rockport, Gloucester or Marblehead.
Iâm not that knowledgeable about Maine. Had a wonderful time in Acadia eons ago and ShawWife has spent time painting in Deer Isle. We tend to visit friends on Marthaâs Vineyard or the Cape when we want to head to the beach. So I defer to others on what to do in Maine.
Our son was born in Concord, and I often worked out of my companyâs Concord office when we lived in the Boston area. I second all the Concord suggestions. Itâs a very special place.
In the past couple of years, the Army has sent DS to Lincoln Labs in Lexington several times while weâve been in Maine. It was fun driving down to have dinner with him at the old Colonial Inn and visit the war monuments which have even greater significance to us now that our son is in uniform. Never in a million years could we have foreseen when we brought our baby home from Emerson hospital that we would someday stand with a soldier near the site of the shot heard round the world.
Itâs a most American place, so worth visiting.
ETA: As an English major, I highly recommend all the literary sites listed as well.
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Mooncusser and 80 Thoreau same owner, different chefs.
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On the trip. So far the highlights have been Concord, Camden, Maine, Campobello island and Woodstock, VT. Acadia was too crowded for my taste. Underwhelmed by the Kanc. Loved the Coolidge sights at Plymouth Notch, VT. Loved Woodstock. Bar Harbor was okay but too crowded and touristy.
Southern VT next. Then maybe the Berkshires.
The trees are coloring somewhat.
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If you liked Woodstock you might like Sturbridge. Mass MOCA (modern art museum) is in North Adams, a few miles from Williams College and the Clark Museum.
My family has had a house in Woodstock for years and years. My brother has it now. The town is a little too perfect for my tastes. Itâs kind of NY in VT. But fun to visit.
Not sure exactly where you are in VT, but Hildene in Manchester VT is well worth the visitâŠin my opinion.
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Not in New England per se, but a few years ago we spent a few days in Bennington, VT and drove 40 minutes west to the Saratoga National Battlefield (or whatever its official name is). Very very interesting, the battle that made the Revolutionary War winnable.
On a rainy day, the Bennington Museum is a fun way to spend some time. They have an old schoolhouse with probably the most Grandma Moses paintings anywhere, along with an eclectic collection of other stuff, including old Bennington pottery.
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