If you’re in the North End, the Old North Church is a must-see. Iconic symbol of the revolution, and beautiful 1720 church. Bova’s Bakery, down the street, cannolis without waiting in line at Mike’s or Modern.
EDIT: And across the street from the church, just up the hill is Copp’s Hill cemetery, with very old gravestones of Cotton Mather et al, with great views. Continue across the river and you’re in Charlestown, Bunker Hill Monument and USS Constitution.
Last time we were there a couple of years ago we took the commuter ferry from Charlestown Navy Yard back to the Aquarium area. Most scenic commuter ferry we’ve been on.
Definitely go to Concord. It’s a great town with lots of history—American Revolution and Transcendentalists. In addition to Orchard House (Alcotts) you can see Old Manse (Hawthorne lived there for a time) and Old North Bridge (first battle in Revolutionary War). Check this website, the Concord Museum offers walking tours.
If you are in town in the evening, check out 80 Thoreau for dinner. The owners also have a restaurant in Boston, Mooncusser. Both are very good.
We recently stayed in Boston one nigh each after arrival and before departure (visited family elsewhere in between). Hotel prices were high compared to our usual travel locations but of the not quite as high but still decent and conveniently located we liked both - Harborside Inn and Canopy by Hilton Downtown. We walked everywhere from them.
Newport and Block Island.
The Block is great is you don’t want crowds. Ferry over. Bring or Rent bikes. Sit on a beach. Hike. Drink. Eat. Be merry. Newport is more crowded but you can go to the water and monuments and attractions on the water
Boston and Minutemen Natl Park
Go to little Italy and get pasta. Walk the Freedom trail. Then go to Minuteman and walk the revolutionary war. If you want a beach go to Hull south of Boston.
Portland and Ogunquit
Portland is fun and funky with Decent restaurants. Ogunquit is quaint and on the beach. We loved Ogunquit. We also found Kennebunkport to be underwhelming
Bar Harbor and Acadia
Acadia is far - but fantastic. Cute town though it closes early in the evening (no late dinners). And the park is just beautiful.
I am no expert on New England, but we just got back from 4 days in southern Maine, after spending time with family on Lake Winnipesaukee in NH. We stayed at an AirBnb in York and explored a bit of Portland (took ferry out to Peaks Island), Ogonquit, Kennebunkport and Portsmouth. We had a nice time and saw some pretty sites, but the trip did not live up to my (high) expectations. Definitely underwhelmed by Kennebunkport. We really enjoyed Ogonquit, dinner on the water in Perkins Cove and our walk along the Marginal Way in early evening (when it was not as crowded.) York is not worth a stop except if you want to see Nubble Lighthouse (can’t go in it; crowds.) We went to Portsmouth the last day and wished we had more time to spend there - and it is the only place I would go visit again if we are up in the area. But that’s mostly because we didn’t have time to get out of the car and walk/shop/eat there - if we had, it would probably be a one and done place to visit as well. All the Maine spots were crowded with tourists, the servers seemed tired and aloof, and we had to eat at off hours in the popular locations. Parking was expensive in Ogonquit but we got free spots twice in KBP. But just know that trying to figure out where to park is part of the exploring of the southern Maine towns. It also takes time to get to them off the main highways/roads, particularly if there is tourist traffic. I thought there would be more opportunity for serendipitous scenic views traveling along the coast, but that’s not really the case (and where it is - there will be traffic!)
It will be crowded in Maine a little. But because the OP is going after Labor Day and before leaf peeping season, it won’t be as crowded. Weekdays should be OK.
Weekends are always busy in Boston. Year round.
I think Wiscasset is a charming New England town…and if you want to see one on your drive…it’s on the way to the Camden area. Wiscasset has a great ice cream place on the way too. The Camden Rockport area has a lot of info regarding the history of seafaring there.
I actually loved Bath Iron Works, but we knew someone who worked there and maybe that’s why.
It’s not as bad in September during the week…after Labor Day. But getting lodging needs to be done asap…which means the itinerary needs to be set at least a bit.
If you decide to drive from Portland to Camden, remember the LLBean flagship store is in Freeport, and I think it’s a fun stop (outlet madness, but the Bean store is fun). Then as you head north, when you get to Waldoboro which is about 35 minutes south of Camden, stop at Moody’s Diner and have pie. I can’t suggest you have anything else there (their soups are OK too), but they have an amazing selection of pies, and they are delicious.
My husband is in Camden right now, and I have requested a piece of their blueberry pie, and their banana cream…both fabulous!
If gardens are your thing Coastal Maine Botanical Garden will blow you away. World class garden. Huge and very charming kids garden included. In Boothbay.
Do you like to “see” things or “experience” things? Your trip sounds like it could be lots of driving. No judgement meant, just different priorities.
When we went to Maine, we stayed a couple of days in Portland, and a full week in Bar Harbor. Some of the other places you mentioned you could spend several days in. If you want to get a better feel for a couple of places, I would suggest limiting the places and spending more time in each.
Perhaps head down to Cape Cod mainland for a couple of days? Or how about taking a ferry to Nantucket? I think a 2 day/one night visit in mid-late September could be nice and is less crowded than normal, especially midweek.
Looks like I will miss the marshmallow fluff festival. So far after Concord Mass. I have booked 2 nights in Camden, Maine and one in Bar Harbor. Not sure after that.
Along with the various houses/museums, I love to go to Author’s Ridge, a peaceful spot where Emerson, Thoreau, Hawthorne and the Alcotts are all buried within feet of each other.
Coastal Maine is beautiful and you have picked a good itinerary. I like Belfast, which is on your way. Have you read Blueberries for Sal?
If you have any interest in artists Andrew or Jamie Wyeth stop in Rockland—it’s probably about 8-10 miles from Camden—and visit the Farnsworth Museum.The Farnsworth has several of their paintings. Also, you can tour the Olson House nearby, which is the backdrop for Andrew’s painting Christina’s World.The Wyeth’s had a summer home in this part of Maine.
Totally second the Wyeth plan proposed ny @Bromfield2 . The puffin info center in Rockport is interesting and a nice adjunct to a tour (which you’ll be a bit late for, but heck, it might still be a fun outting.) I am recommending this having never gotten the timing right and feeling sad about it each time. Iow, if you do this, I’ll be thrilled vicariously!
Visit Salem MA and go to the House of the Seven Gables and the Peabody Essex Museum. Before the port silted in, Salem was the richest city in North America. Walk around the McIntire district. There is some kitschy witchcraft stuff but you can ignore it. Visit Portsmouth NH.
@NJSue I drove through Salem today and it is already overrun, even on a weekday. So crowded. You cannot ignore the witchcraft (and pirate!) stuff. I would avoid at all costs if you don’t like crowds.
I know you have lived in Essex County and I do not (my daughter lives in Salem) but there are tourists and crowds in places that are interesting, and Salem is interesting. I live on the Jersey Shore and there is plenty of traffic in the summer. I guess it is up to people to decide how much crowding they can tolerate. Boston is crowded also. Salem is on a train line and there is also a ferry, if one does not want to drive. I can understand avoiding Salem in October, for sure.
