Highlights of New England for me are the Cliff Walk at Newport, Mystic Seaport, Shelburn Museum in Vermont (temporarily closed), many villages in Vermont like Woodstock and Danville in the Northeast Kingdom, and of course Acadia National Park.

Connecticut has a lot of interesting little seaport villages like Stonington near Mystic. Boston is great, of course, and I like the Natural History Museum at Harvard. I don't care at all about Mt Washington or the mountains in New England in general.

I am always reminded of the skit in Beyond the Fringe by Peter Cook and Dudley Moore about the couple from England trying to find out where the 'typical America' was. After eliminating every other region because of some peculiarity (the South, for example), they finally conclude that, of course, New England is the real America.

Kennebunkport is only a 25 min drive from Portland. A day trip encompassing Fort Williams /Two Lights then down to Higgins Beach to Pine Point and then Ocean Park, on through Biddeford Pool and ending in Kennebunkport is about 80km and you'll get a great sense of what southern Maine is all about. Lots of nice spots for dinner in Kennebunkport. You can return to Portland via interstate 95 and so the return trip would be 20-25 minutes.
Or, you could do just 2 nights in Portland and then stay down the in Ogunquit on your 3rd night if you don't like the "backtracking". Ogunquit gets a lot of mention for being too trafficky and touristy in summer, but in early October it is a very relaxing place to spend a day or two.

Don't worry aboout doubling back. You will go to Boston via I95. Although you can do I95 some of the way to visit places south of Portland you can also do USrt 1 but it is much slower.

CindyJ thank you so much - we will take your recommendations into account and are planning to stay In Portland - do you have any recommendations of some good places to stay? we have decided not to do the cog railway and to spend more time on the coast

We like scenery, photography, not massive foodies, some history, not art really. More soaking in the new places and views

Ah brilliant thank you

Sounds good, we are going to spend a bit more time here now so we will be able to take this into account thank you

Think we almost have our plan - just need to finalise the top part across from Manchester VT to Portland

When I was in Portland a couple of years ago, I thought this Hilton was in the best location. https://www.hilton.com/en/hotels/pwm...wn-waterfront/. It's right in the middle of the main drag. Unfortunately I was booked several long, uninteresting blocks away. Next time!

Thank you :-)

Unfortunately, hotel/inn prices in Portland are astronomical! And of course as locals we don't really know the quality of the hotels. I would look around for the best price, there are lots of new hotels in the Old Port area which makes it nice for walking around, etc. But if you're not really into the small, historic city vibe with food, bars, etc. I would consider staying outside of town. The Inn By the Sea in Cape Elizabeth is lovely, and probably $$. But you have a view of the beach and can walk to a beach (Crescent Beach State Park) and a nice little cove/rocky area (Kettle Cove). Cape is also home to Portland Head Light (my earlier photo) and another lighthouse - Two Lights, and Two Lights State park is a beautiful rocky bluff for picnicking, views, etc. Air BnBs are being limited a bit so you may have trouble finding a house, but its worth a shot. A somewhat unusual accommodation is the Spring Point Inn in South Portland - https://www.smccme.edu/business-comm...ing-point-inn/. It is part of Southern Maine Community College, a 2-year school that has a hospitality and culinary program and runs this inn. I haven't slept there but have been there for business meetings. It has lovely views of Portland across the harbor. Sort of a hidden gem.

Don't hesitate to ask if you need more info on our area. I have gotten such great info on the Fodor's boards for my trips - its time to give back!

Thank you Cindy

You aren't wrong lol - i've found prices to have sky rocketed since we originally started this booking in 2020. I found a beautiful place in Kennebunkport but the price wow

Im more about the scenery and small town prettiness than big cities - we are doing Boston for a few days to get out city fix.

I have found these forums invaluable so thank you for your input - im thinking maybe 1 bight now in Portland then one further south around KP or Rockport maybe on our way back towards Boston.

Portland is a beautiful small city with neighborhoods. I've already mentioned the great view of Casco Bay from Fort Williams Park but you can also het an interesting view from the other side to the north. Very popular picnic area, laumch ramp and possibility of seeing people with their stand up surfboards paddling around. Eastern Promenade. A friend lcuk to habe a relative with a cottage on Peaks Island said I would love it. Perhaps Cindy can say yea or nay. You get it bu taking the mailboat/ferry. I think there's a golf cart tour. Kids on the island go to school in Portland so the ferry is their ‘school bus’.

Portland won't give you a big city vibe. The population is only around 80,000. Lots of old brick buildings and renovated homes on both the Eastern Promenade (which the other posted is a great spot) and Western Promenade which is dominated by our state's largest hospital that is an architectural wonder of its own. Its been added onto so many times! But you can do all that staying a bit out of town too. Did you check out the Spring Point Inn?

Not sure if this interests you, but there are many covered bridges near Keene, NH.

Covered Bridge Tour - Monadnock Region of Southwest NH

By the Maine NH border check out this beautiful light house in this setting.

Nubble Light

this fall we're staying in Rockport, Mass. Looks very pretty.