First off, if you really want to see things and get a feel for the character of a place, only drive on the Interstate highways when you need to make time. Your GPS will of course give you the fastest route on the interstates, so a little map review before you start driving will show you some good alternative routes. . Also, I prefer to eat at local restaurants, not chains like McDonalds, whenever possible, you will usually see more interesting people, and sometimes get tipped to places off the beaten path that you'd otherwise miss. I recommend loading Trip Advisor on your device of choice, I find it has a good balance of informative reviews.
Maine and the rest of New England, along with New York State, are beautiful, but will be cold at least at night, and you might get snow in November, so be prepared. I recommend stopping in Camden Maine and going to the top of the hills overlooking the town and the harbor, an incredible view.
I love Boston, and NYC, but I do not like driving in either city, traffic is often challenging, parking is expensive. Between Boston and NYC, train travel is actually reliable and not too expensive, consider using that, and you get to take pictures rather than watch taillights.
FYI, the best view of the west side of Manhattan is from Liberty State Park in NJ, and IMO, the best way to see as much of NYC as possible is to take a Circle Line boat tour around the whole of Manhattan Island. You get to sit in comfort with your favorite beverage while the view changes, and get to see a lot of landmarks from a unique POV,and hidden treasures you would never see otherwise. Once you get off the boat, you feel like you've seen almost everything on the island, and still have time to hit the inland sites.
Boston is my favorite city, and very walkable, and public transit is reliable, so if you are touring the town, ditch the car. When I visit that city as part of a visit to New England, I usually turn in my car a day or two before I depart, I don't need it or want it. You must see Fenway Park, one of the oldest (1912) baseball parks in America, take the tour, because it is a one of a kind place inside. The neighborhoods around the area have neat architecture, and there are actual fens nearby, now a lovely green space. The waterfront near the Quincy Market is another place to see, as is Boston Common, I've walked all of that in the course of a few hours, stopping to take a lot of pix.
Something you might consider, if you have a free day and a car, is to visit Cape Cod, the arm extending 80 miles into the ocean east of Boston. It's a wonderful place, and the late autumn light and the sea is like nowhere else on earth.
Enjoy your trip, you can't see it all no matter how long you visit, the region you are visiting is vast, but enjoy what you do get to see. I look forward to seeing the resulting photos.
Last edited by robgski; 10-17-2018 at 05:07 AM.