We are a commune of inquiring, skeptical, politically centrist, capitalist, anglophile, traditionalist New England Yankee humans, humanoids, and animals with many interests beyond and above politics. Each of us has had a high-school education (or GED), but all had ADD so didn't pay attention very well, especially the dogs. Each one of us does "try my best to be just like I am," and none of us enjoys working for others, including for Maggie, from whom we receive neither a nickel nor a dime. Freedom from nags, cranks, government, do-gooders, control-freaks and idiots is all that we ask for.
A Canadian reader asked for a post on this topic. A complicated topic, because it depends on the season and on your interests. It's a varied place for such a compact area, with rivers, lakes, mountains, coasts, islands, rural lands, some charming antique towns, lots of decrepit small towns with tattoos, meth labs, and empty old mills; a handful of booming suburban towns of little interest, plenty of music, theater, and dance festivals, and a small handful of pleasant cities.
When driving around, one must bear in mind that most industry, and farming, fled New England in the past 60-100 years for more business-friendly and farm-friendly locations, so it is no longer the prosperous heart of America. Now it's mostly "Blue states", if you know what I mean.
For road food, I'd recommend diners, diner-like one-off places, and seafood shacks instead of fast food chains. There is even an excellent southern barbecue joint on Rte 91, as rickety as heck and the real deal (only during summertime - owner lives in Mississippi). With all the immigrants, there is good Thai food almost everywhere, but the Chinese food in New England tends to be terrible as does Italian food outside of cities except for pizza.
Rather than describing the places I know and enjoy, I'll list just a few and refer you to some good resources. For local flavor, I like Grand Manan Island (between Maine and Canada), Monhegan Island, Camden, Maine, Kennebunkport is touristy but Acadia Park, Cape Cod (Chatham, Wellfleet - lots of Quebec and Ontario license plates there in August), Block Island, The Massachusetts Berkshires - Lenox, Stockbridge, etc - Boston (haven't been there for years though), touristy Woodstock, VT, Stowe, VT, Lake Winnipesaukee and Squam Lake (New Hampshire), Watch Hill and Newport (Rhode Island) - well, it's too much to list and I'll leave too much out so I'll quit there.
We like Karen Brown at lot (her guides for places all around the world are our favorites), and she avoids fancy modern hotels that can make you feel like you are anywhere.
Now that Canada is recovering from Trudepia, perhaps a colonial tour is in order. Canada as we know it is the direct result of the American Revolution. Tories leaving new England for Canada changed the demographics from predominantly French to overwhelmingly British. Nice tours starting from Montreal would include the lake Champlain campaigns then following General Knox's route to Boston.
Consider 133 crossing @ st Armand to vt 89 above st Albans. Take rt 7 thru Burlington and aim for 22/ fort ticondaroga. Possible stops include state parks on lake Champlain such as button bay Shelburn museum and hiking @ camel's hump or mount mansfield. Suggest audio book last of Mohicans.
Next take 4 to Rutland. Then 7 as back way to berkshire @ north Adams. Fr border to berkshires is about 5 hous of just driving. Grandparents lived in shelbourn and we lived in lee.
Stretch legs at mt greylock. Continue on 7 and enjoy quaint towns such as Stockbridge. If summer consider a picnic basket and Tanglewood (but expect traffic and tourist pricing - in Lenox greatbarrington stockbridge. Grew up out this way and you pay for the "name" in these towns but you won't get extra quality in lodging or food just extra pretense and cost so consult urban spoon and other filters to find the quality and experience you want. Still they are nice tor walking, visiting small shops and a treat like coffee. Consider Otis for staying. It's on the Knox trail and Appalachian trail is also near by.
I would take the mass pike to Boston. Good food, shopping, freedom trail, sports. Bypass the cape unless it's shoulder season. It's over rated vs traffic unless it's shoulder season or you have a house there (and even then the traffic on and off is a suffer fest).
95 to Bangor is better. Stay in bar harbor and visit Acadia park - a glory in fall. From there to mt Washington new hampshire. The lake district there is nice.
Then out the back way via the finger lakes of ny and crossing @ niagra. You could do that in a week. Two weeks would be better.
I am sorry for your loss. I grew up free range and ferrel on October mountain.
BD I remember that midnight road...sitting in my car packed bumper to bumper thinking when's the movie going to start...oh wait, wrong parking lot. Seriously if these folks r from Montreal or other large city, no problem at the times you recommend although the restaurants n such will be crowded and grumpy Yankees are certainly a local flavor...that might be interesting to tell stories about later...maybe. Large, sunburnt, should be wearing more clothes. If on the other hand rush hour is a few cars behind a horse buggy or rubbernecking at the moose (like it is where i live now) then not so much.
Eat at Anthony’s by the Sea 153 Humphrey St. Swampscott Ma. (It may now be called Hawthorne by the sea). I prefer to do lunch there and sit by the window or if the weather is good on the deck. You can see all of Kings Beach all the way to Nahant. And beyond that you can see the skyline of Boston. They have the best lobster rolls and real quahog clam chowda. Kings Beach is a beautiful beach to walk and Red Rock is a great place to sit and watch a nor’easter. From there you can easily drive South to Boston or if you are going North to Salem or Marblehead. If I were headed to NH or Maine from there I would drive up old rte 1A. You should detour to drive through Essex and try the fried clams at Farnham’s. If you love old wooden boats visit the Essex Shipbuilding Museum. It’s not some large fancy museum but it’s the real thing. You will turn onto Rte. 1 in Newburyport, which is an old New England seaport. If you are there in the Summer visit Salisbury Beach. They used to have a big old wooden roller coaster there just like the one at Revere Beach but I think they may have closed it. I 95 is right there to take you into NH and Maine but resist the temptation to take it. Stay on Rte.1 for the scenery and salt marshes. You can take Rte. 1 into Portland be careful not to be tricked off of old Rte. 1 onto one of the featureless highways like 295. You can keep heading North towards Rockport, eventually this will take you downeast. The scenery is awesome but the driving can be tedious; mile after mile of rocky coastline, beautiful views and fewer and fewer cars to share the road with.
I still think one of the best ways to discover “old New England” is to try to find all the old covered bridges. They are mostly out of the way and in small towns and back roads and mostly in beautiful places you won’t find any other way.