Boston, Cape Cod, Maine, Vermont and Berkshires
 

VT 30 from Brattleboro and then VT100 are the roads that goes up the center of Vermont and passes through many of its small picturesque towns.

Sounds like a great trip. Wondering how you are getting around - will you have a car? If so, you could wait to pick it up until you are leaving Boston as it will be an added expense and not necessary in Boston.

Some random suggestions. Boston: There is a walking food tour of North End (Michelle Topor company) that is excellent. They also have one of Chinatown, which is good, but not as good as the North End tour. We have had several visitors from UK and for some reason I do not understand they all wanted to go to JFK Library. Easily accessible on public transit. If you want to do any museums, Isabella Stewart Gardner Museum would be a great choice (I would pick it over Museum of Fine Arts) but I personally love ICA - Institute of Contemporary Art (but I would probably be in a minority opinion on that). For getting around town, Uber works great in Boston. Or public subway/trolley which is called the MBTA. Their website mbta.com will give you routing from Point A to B. Strongly recommend trolley/subway over bus routes.

Cape Cod. Take a drive to the tip of Cape Cod - Provincetown. You will pass the dunes in Truro. Provincetown is a unique town. Especially in the off season it has a large gay identity, but everyone can be comfortable there. Some great seafood. Lots of little unique shops and galleries. Cape Cod National Seashore is consistently ranked one of the most beautiful in the US. There is entrance and parking in Easton. Since your first day on the Cape is a Friday, if you can start your drive before noon you will avoid weekend traffic, which can be annoying even in September.

Portland. Another great choice. Do a little research and visit some of the lighthouses along the coast. I know you have a house rented in Portland, but it is about a 3 hour drive Portland to Bar Harbor and Acadia National Park which is beautiful. However, I really agree with and respect that you seem to be choosing to actually see each of your areas rather than racing from city to city. Great plan.

Can't really help with Vermont.

Assuming you are flying out of Boston/Logan after Stockbridge, if you have time you might consider taking Route 2 rather than the Mass Turnpike east. Much more scenic and at that time of year cute little farmstands along part of the route.

I am surprised you have not received more responses to your post - others may be able to give you more specifics.

It sounds like you won't have a car on the Cape? You really need one to explore that area. It is very easy to drive around. Leaving Boston and going to the Cape that time of year will not be bad. Just don't leave during rush hour (wait until 10:00 to leave Boston).

Your trip sounds like fun. You will love New England.

Great advice so far. Don't take a car to Martha's Vineyard. Once there you can take a van tour. Depending on ferry time it will dock at different places. We liked walking around Oak Bluffs to see all the gingerbread cottages.
Peabody Essex Museum in Salem is very nice - make sure to include the Chinese House.
Mid-coast Maine is our favorite area to explore. Acadia is a gem but would require too many hours on the road. Yankee Magazine has said Camden is the prettiest town for fall foliage. Take the auto road up Mt. Battie for an incredible view. Lobster shacks are usually open weekends only after early September so check ahead and since you usually eat outdoors at picnic tables weather will be a consideration. There's plenty of restaurant choices. I like the Farnsworth art museum in Rockland because it features Maine artists and has a lot of work by the three Wyeths. My husband prefers the antique car museum in nearby Owls Head. Claws take out restaurant on Rt 1 just north of Rockland has a great menu, not a great view of the harbor and covered porch dining. If it's open, go their for lunch.
You have to drive thru NH to get from Portland to Grafton. Google Maps says slightly more than a 3 hour trip. This gives you time to make some stops on the way. Quickest way is to take Rt 101 but it's a boring limited access highway. More scenic route is Rt 4 to Concord and then to Warner NH. But both suggested route west from Concord NH are rural and scenic. You can take local roads from Concord to Warner thru some quaint towns with possible slight detour to Gould Hill Orchard (they make their own hard cider) which has a pleasant view toward the mountains. Warner features a small but interesting Indian Museum. You can drive a good part of the way up little Mt. Kearsarge then hike. The Wilmot side of the mountain also has a toll road which ends with great views looking toward Sunapee (Winslow State Park). You can hike the rest of the way but no need to. Warner is probably your last chance for lunch. If you take the southerly route, Henniker and Hillsboro are you last chance for lunch until you get to Keene which is a college town with a great variety of restaurants. If you just want to stop for coffee and snack, Concord has a nice walkable downtown. Crust and Crumb across from the State House is a wonderful bakery. At the south end of town, Bread and Chocolate is more European style bakery. You might want to visit League of NH Crafts for upscale handcrafts.

Grafton is near one of the Vermont Country Stores which are fun to visit. It is also near Norwich which has King Arthur Flour if you want to pick up some baking ingredients. The farmers market on Saturdays is wonderful with live musics, food samples and a nice variety of things to eat like pastries, etc. The east side of VT is forested while the west side along Lake Champlain is rolling farmland. Just about everywhere is great to explore. You might want to visit St. Gauden's in Plainfield/Cornish NH. This is near a very long covered bridge. If you want to find covered bridges, get a copy of the DeLorme Atlas and Gazetteer for VT. There are several small covered bridges in the Warner area but you would have to make a slight detour. There's some famous (although small) stone arch bridges in the Hillsborough NH area. Hillsborough?s Stone Arch Bridges | Living History Event - Historic Hillsborough, NH

The mailboat cruise of Casco Bay from Portland ME is fun but I think the inland rivers one from Portsmouth NH is more scenic where foliage is concerned. Also, the view of Casco Bay from South Portland Fort Williams Park is wonderful. From the north you get a different view from the park on Eastern Promenade.

You might want to check out Jeff Foliage's website. He is based in Salem MA but explores rural New England. Pretty good photographer. Visits VT a lot since his wife is from there so you might get some good tips on scenic places to visit.

Listen to dfrostnh - although I am not familiar with some of her suggestions, she is always very useful and accurate about this part of the US

Sounds like a great trip. I ran into one problem with my rental and that was the toll pass. The rental car did not have one and they neglected to tell me I needed it. I pulled over and set my GPS to non-toll roads and did great. Vermont is one of my favourite places in the US. Do stop in many of the small towns. Check the weather if the seas are bad the ferry won't go to MV. We loved going to Nantucket and it is easy to walk. There is a ferry that takes you to Provincetown on the cape to avoid all that traffic from Boston. I have been there in Sept, October and July and the traffic was bad getting on and off the cape. I love Beacon Hill. There is a ferry you can take to Salem and the boat ride alone was great. I had relatives involved in the witch trials so went for that but the town is very interesting and worth a visit.

Sorry, just checked the Boston to PT ferry and it is for foot pax only.

Enroute to Portland, you can stop in Salem and see the national historic port area. Salem Maritime National Historic Site - Salem, MA


I agree with dfrostnh’s suggestion about the Peabody Essex Museum https://www.pem.org/.

Things to do in Salem: https://www.salem.org/10-free-things/



Whale watching season in Massachusetts is from April through October, although you’ll be there near the end of the season.. If you take an excursion, ask if they have a naturalist on board. Bring a jacket– it can be cold on the water.

Links to the various locations for whale watching excursions from Boston, Cape Cod, Cape Anne, etc.

https://www.affordable-cape-cod-vaca...achusetts.html

Thanks bachlunch, Macross and gbelle1 for the excellent suggestions. I’m fascinated by Salem and your guidance on what to see and what to avoid is very helpful.
Equally appealing is the potential for whale-watching, although important to recognise we are probably at the end of the season for this.
The variety of the experiences we can look forward to on this long-awaited holiday is incredible and so exciting.
May thanks again for all this advice.
Lisa

Pay attention to what macross says about toll roads. Mass. toll roads are now cashless - no option at all to pay with cash. Your choices are getting an EZ Pass transponder, or utilizing PlatePass, where they take a picture of the license plate and bill the registered owner (= rental car co). Most if not all rental car co's will tag on exorbitant fees if you use the PlatePass - not just the fee for the toll but likely a daily access fee for every day or your rental...

I don't know the best way to deal with this for non US residents - maybe others have good ideas.
Personally, I own an EZ pass transponder issued by my own state, NY, that I keep in the vehicle and it's good for any tolls I ever use in any state, ranging from Chicago to Maine and down to FL.

If you did not want to make the drive from Boston to Portland ME, you could take the Boston rental car back to Boston and take an Amtrak Downeaster train from Boston North station to Portland and rent a car in Portland Maine. In Freeport Maine, the Amtrak station is within walking distance of the LL Bean flagship store.

I'm including some random ideas about things to see in several of the locations you plan to visit. Be sure to check to see whether sites you want to see are open. Some will close in the fall especially after Columbus Day weekend (Columbus Day is October 14 this year so you are probably safe)

In Boston Beacon Hill is a lovely and interesting area and I am sure you will enjoy staying there. In addition to the Freedom Trail I would recommend the Black Heritage Trail which is on the hill. The main indoor site to see is the African American Meeting House
https://www.nps.gov/boaf/planyourvisit/things2do.htm
I have also enjoyed touring the Nichols House museum for a glimpse inside one of the Beacon Hill town houses owned by a prominent Boston family.

I'd recommend spending some time viewing the Shaw memorial opposite the state house in Boston then going to the St. Gaudens Historic site, home of the sculptor, when you are in Vermont.

The Freedom Trail is much more than a walk through the city; it features many sites to visit inside and takes quite a while. You might want to break it up.

In Cambridge, in addition to Harvard Square and the Harvard campus, Harvard has some excellent museums (art, natural history, archeology and ethnology). The Longfellow House National Historic site is also well worth a visit. It is off of Brattle Street which was Tory Row, where many Loyalists had mansions at the time of the American Revolution.

Stay flexible about your itinerary driving over to and around Vermont and the Berkshires since it makes sense to spend some of your time driving to areas where there fall foliage is at peak. There will be updates during your trip. There are many scenic drives on secondary roads. If you want to investigate some cheese and/or beer there are trails featuring both.
VERMONT CHEESE TRAIL ? Vermont Cheese Council

Like dfrost, I would recommend the St. Gaudens site just over the border in New Hampshire. Other good places to visit not far from Grafton would be the Marsh Billings Rockefeller Park, Scott orchard (heirloom apples) to the south in Dummerston, the Calvin Coolidge state historic site in Plymouth Notch

Near Stockbridge area some good places to visit are Naumkeag, the Mount and the Hancock Shaker Village.

On Cape Cod, definitely plan to spend time at the National Sea Shore. There are a number of different areas to visit. Check the ranger programs for special hikes and activities.

If you are interested in the Shakers, Canterbury Shaker Village isn't very far from Concord NH which you will probably have to pass through on your way from Portland to VT. They have very interesting tours and it's a beautiful rural area.

I am not sure what route you were planning to take from Grafton to stockbridge, but I would recommend something other than driving on the interstates. There is an alternate route shown if you check google directions that takes you west then south along Rte 22 in New York State.
If you do go via highways 91 and 90, you might consider stopping briefly in Historic Deerfield MA which is very easy to get to off I-91. Even if you don't get a museum pass and go into any of the houses, the main street is lovely. There are many early (for the U.S.) colonial homes
https://www.historic-deerfield.org/

I would ask rental car about options for the tolls. I was about 30 miles away when I figured out I needed a toll pass.No credit card option as there are no toll booths. I switched my gps to non toll roads and it was great but don't know about the cape as we were riding in a friends car that has a pass. Are there toll roads going there? I know the rental car places charge a fee on top of the toll fee. Ask them if it is a one time fee. I got a convenience fee one time and it was 16 dollars in Delaware on a 1.00 toll fee. If you purchase a toll pass you normally have to register it to the auto.

I use google maps on my phone for navigation and like the vocal directions. My husband prefers to look at a map first to get a general idea of which way he wants to go. If you like detailed paper maps you can get a DeLorme Atlas and Gazetteer for each state you want to explore. All the roads, including seasonal will be shown. They also show locations of covered bridges, waterfalls, and other interesting things. You can buy them at various gas stations and bookstores in the US. Fold up maps from gas stations are ok but sometimes not detailed enough.

For navigation you can also download the free WAZE app to your phone or iPad. It gives real time information on routes and will tell you when there are accidents, road hazards, police etc. on your route.

That is good info from alamo. I could not remember the Cape tolls as I was sitting in the back seat. Good to know as there aren't any back roads. My friend Lauren lives in Springfield and she picked us up in Hartford this last trip. We got the car after the Cape to head to the Adirondacks and Vermont. I will ask for the toll pass next trip but did enjoy those back roads.