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In the beginning of October we are traveling by auto to Cambridge, Massachusetts and will be spending 3 days touring the Boston area. From there we will be driving to Kennebunk, Maine and spend 2night and 3 days in the area. From there we are going to Bar Harbor and spending four days.
We are looking for recommendations of what to see on our trip from Cambridge to Bar Harbor.
Also looking for suggestions for a route home to Chicago and what to see and where to stay on that leg of our trip. We are interested in scenary and soaking up the New England atmosphere and history.

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    Several hints:

    You have surely read here to park the car in Cambridge and use public transportation to get around the city. That is good advice. The only time you would use the car is to go to one of the outlying historic sites in Lexington or Concord.

    Kennebunkport is a bit south of where I would stay in Maine, but you can certainly use it as a base to visit lighthouses, Portsmouth and Portland, and Ogunquit.

    The good stuff in Maine is in general not on the major highways. Except for Wiscassett, Rockland-Rockport-Camden, you have to leave the highway to see what you expect to see in Maine, rocks and waves. A lot may be closed on October or open only on weekends.

    You should return to Chicago through New Hampshire, Vermont, and the Adirondacks. You can do this on US 2 ( spectacular views of the White Mountains, likely to be covered with snow) and plenty of fall color in Vermont. I would eventually intersect I-89 and go to charming Burlington. From there, you can take the Lake Champlain car ferry to the Adirondacks or go via Montreal, Toronto, and Niagara Falls. though you will need all your papers to cross the border. All road eventually lead you to I-90 and home.

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    You might be late for good fall color in NH/VT/Adirondacks. I am a little confused about the dates you would be headed back toward Chicago.
    I live in north central VT and foliage usually peaks here the first week in October. It would be a little later around Lake Champlain.

    If you go into Canada you need a passport or enhanced driver's license.

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    New England history would include Strawbery Banke in Portsmouth NH which is on your way to Kport. I would go on the inland rivers boat trip but it might be a little early for color. Fascinating narrative though. We like the scenic drive from Strawbery Banke on Rt 1B thru New Castle which goes past the restored Wentworth by the Sea hotel.

    Check to see what Maritime Museum in Bath ME might be offering. Nice view from top of Mt Battie in Camden (take the auto road) or visit Pemaquid Point Lighthouse.

    When you cut across Maine you could go via Bangor so you can visit the Cole Transporation Museum. Unlike the typical classic car museum, this one is devoted to work vehicles. Kind of dusty but pay attention. The Lombard Log Hauler pictures were fascinating and we later saw a restored one at a special event at Owls Head Transportation Museum in Rockland ME. There is more to Maine than lobster.

    If you head to NH's White Mountains I suggest instead of taking Kancamagus Hwy, go south on Rt 16 and then west thru towns of Tamworth and Center Sandwich. You can connect with I93 or take state hwy thru White Mountains and then cross over into VT. There's a country fair in Center Sandwich on Columbus Day weekend. Small but if you want to see farm things, it's an option and Center Sandwich is a pretty town. Try to figure out what people were doing settling that area so early in American history. Although popular with kids, we enjoyed recent visit to Squam Lakes Science Center in Holderness. Meet NH wildlife in a very nice outdoor center. Except the moose is fake.

    We had an interesting visit to the Lake W area in winter to see Model T snowmobiles. The gear to put skis and tracks on a model T in the winter was invented near by. And there's really not much to see besides great scenery in the Center Sandwich area but that's wear sled dogs were trained for polar expeditions. We have not been to the Remick Museum in Tamworth.

    I agree with suggestion to connect with I89 to VT but it's hard to say where. Had an interesting tour of the house at The Fells, one of the summer estates built by a rich family years ago when Lake Sunapee was a wilderness area.

    Stop at King Arthur Flour in Norwich VT if you like to bake. I took a class yesterday and a lot of people were doing a class while they were on vacation. The store is great. You can check out their on-line catalog.

    Also, the Shelburne Museum south of Burlington VT is excellent for history.

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