Help with New England Road Trip Please
 

Really stuck right now - original trip was put off twice due to covid & planning despite googling the **** out of it still has me stuck - mainly because i know i want to do too much.

Details - 2 UK travellers in late 40's - used to cramming lots in e.g. we flew to San Fran and did the city, Lake Tahoe, Yosemite, Mammoth Lakes, Death Valley & vegas in 11 days!!! yes we were knackered ;-)

Dates mid sept - early oct 14 nights - Flying into Boston from London late eve so have booked the first night at the airport to recover then pick up car the next morning.

So the plan was to drive down to the cape for 3 days - staying i Chatham and PT with a visit to MV and/or NT - the cape is a non negotiable as the hubby is a big film fan and wants to see locations etc.

Then onwards to RI to see the mansions.

The idea and this is where it gets tricky was to drive up towards the mountains and across the Kancamagus Highway to white mountains, then across to the coast and down to return for 2 days in Boston before flying home.

We wont be hiking as in (long day trips to hike) we aren't going specifically for fall colours but of course will really enjoy seeing what we can but it isn't the purpose of our trip.

Ideally we would take 2 trips to see more of each area but being from the UK with so many other parts of the US and other countries to visit - i'm torn between seeing a taste of whats to offer and coming back to do a trip in the future to revisit favourites or see areas we couldn't get to vs seeing as much as we can in case we never get the chance again.

I have googled so many itineraries some of which seem to flash through it all in a week then others saying you need 3 weeks which we do not have.

I am under no illusion that we wont be able to spend lazy days pottering about and will not see everything there is as you would if you just visited 1 or 2 states but even with the books i've also bought i'm struggling to plan a doable itinerary that takes all of this into account.

So your expert advice would be highly appreciated.

​​​​​​​Many thanks

After doing the Cape and Rhode Island, maybe swing back up thru western Massachusetts and southern Vermont and New Hampshire on your loop back to Boston? New England states are very small (compared to your trip out West) so you can cover quite a bit in a day.

From Rhode Island you could go to Connecticut and visit Mystic:

https://flic.kr/p/7vx3fi
and from there drive to Sturbridge to visit the historical village:

https://flic.kr/p/2hJnLKx

Good idea to swing through western Mass after RI en route to Vermont, NH and Maine.

Northampton/Amherst, MA (three colleges)

Brattleboro, VT (lively town)

Montpelier, VT (hippy haven).

Then take US 2 to

Bar Harbor (Acadia National Park)

Stonington (authentic fishing village)

Castine ME (quaint downtown)

Bath, ME (historic maritime destination)

It will take half a day to get a car and drive from the airport to Province town, longer if you stop at the National Seashore VC. I would do that on the first day then head back to Chatham.

If you want to see Martha’s Vineyard OR Nantucket, do that on the last day and find lodging that night near the ferry or on the way to Newport to avoid driving back and forth. I would not take the car over to either island, use public transportation or taxi/Uber/Lyft or rent bikes when you get there.

The distances are not great compared to the west, but the roads can have traffic and speed limits are much lower.

Thank you - thats good to know - ive seen so many posts saying going through all states is too much - appreciate your reply

Thank You Michael great photos - Mystic definitely sounds good

Sorry PrairieHiker, I'm pretty sure we have been on that US 2 route to Bar Harbor which is very scenic and very rural. Very few restaurants. Might see used skidders for sale on front yards. I checked google maps and although it adds 100 miles to head south on I89 to connect with I95 in Portsmouth you only add less than an hour to the trip. Although I89 is an interstate it's also fairly rural and scenic and gives you more of NH than just skimming the top of the White Mountains. You could add Portsmouth NH and a boat ride plus a visit to Strawbery Banke. I like the inland rivers best.
on the way you could make a slight detour to tour Canterbury Shaker village.
Portsmouth could also be visited on way south from Maine to Boston.
Or take a detour to include NH's Lake Winnipesaukee and Squam Lake. Highly recommend nature cruise on Squam Lake if they are still running it. We saw loons at beginning of September but they start migrating to the ocean. Squam Lakes Science Center if youmwant to see NH wildlife in nautral surrounds. Great wildlife lectures and demos.
I agree with Bath as an interesting part of Maine. Great boat rides to see light houses if Maritime Museum has any scheduked. If tiu need anything go shopping at Remy's. In addition to Bath they have locations all over Maine.
Message in a Bottle has a water scene we knew was not the Carolina coast. Maine Popham Beach.
If you want Jaws story for MV visit read obituary for Lynn Murphy.
I would give Maine a priority if you want possibility of eating outdoors at a lobster shack. Many are weekends only after Labor Day and close Columbus Day weekend.
The larger farmers markets are a chance to stretch your legs and talk to locals. My favorite is Saturday in Norwich VT but Brattleboro is good too. Brunswick Maine on Fridays. These markets have some prepared food options. There are some country fairs and foliage festivals which you might not want to visit but might cause some traffic delays.
favorite RI Mansion tours are Beneath the Breakers and another mansion tour of servants quarters.
NH Animal Science professor Drew Conroy amd his oxen have been in movies, most notably The Crucible. Here's a link to his biography. We had him as a speaker for a 4H event. His parents tried to discourage him from having oxen necause it was too old fashioned and told him if he ever decided to give up they could always eat them. Turned out he became an expert who had adventures around the world thanks to oxen. The Ox Man

Thank you so much for that detailed reply - we have had a play this morning and have this as a suggested itinerary

UPDATE

day arrival arrive late into Boston - stay at airport
day 1 drive down to Ptown stopping at plymouth & maybe other little stops along the way - spend first night there
day 2 spend the day in ptown possibly doing a whale watch then drive to chatham & stay there
day 3 chatham area and day trip to nantucket then drive down to falmouth and stay there
day 4 falmouth - 1/2 day trip to MV (not too worried about seeing everything there just to see the jaws bridge) drive to newport stay there
day 5 newport mansions spend second night newport
day 6 drive to mystic and then new haven? stop for a quick look (not sure if new haven is worth the stop? drive up for a longish trip to manchester maybe stopping off in stockbridge to break the journey - spend the night in manchester
day 7 drive to lake winnipesaukee (another biggish drive) spend rest of the day there and spend the night in that area towards conway
day 8 drive the kancamagus highway with stops and spend the night in lincoln
day 9 drive to mount washington railway and take the railroad up, then drive to portland
day 10 wake in portland and then we have days 10, 11 & 12 to either see that part of the coast (do we need that long?) should we alot one of those days to stay extra along the route?
days 13&14 in boston before home day 15

excuse the spelling and lack of caps etc

update to NEW ENGLAND Road Trip Help
 

Further to my last post - this is what we've come up with.

We have also realised that Sept 17th our first day is Constitution Day & everything left on the Cape is either super expensive or not where we want to be - bearing this is mind should we reverse the trip starting by going up to portland and then the whole thing in reverse ending up in cape cod then Boston?

day arrival arrive late into Boston - stay at airport
Day 1 drive down to P-town stopping at plymouth & maybe other little stops along the way - spend first night there
Day 2 spend the day in P-town possibly doing a whale watch then drive to chatham & stay there
Day 3 Chatham area and day trip to nantucket then drive down to falmouth and stay there
Day 4 Falmouth - 1/2 day trip to MV (not too worried about seeing everything there just to see the jaws bridge) drive to newport stay there
Day 5 Newport mansions spend second night Newport
Day 6 drive to mystic and then New Haven? stop for a quick look (not sure if new haven is worth the stop? drive up for a longish trip to Manchester maybe stopping off in Stockbridge to break the journey - spend the night in manchester
Day 7 drive to lake Winnipesaukee (another biggish drive) spend rest of the day there and spend the night in that area towards Conway
Day 8 drive the Kancamagus highway with stops and spend the night in Lincoln
Day 9 drive to Mount Washington railway and take the railroad up, then drive to portland
Day 10 wake in Portland and then we have days 10, 11 & 12 to either see that part of the coast (do we need that long?) should we allot one of those days to stay extra along the route?
Days 13&14 in Boston before home day 15

It is best to keep your posts together so people can see the whole conversation -- maybe ask the moderators to merge your two threads.

Sorry Im new to this - i dont know how to do that

Not to worry. See that little orange triangle? Click that and you'll get a dialog box - it will say something along the lines of 'to report inappropriate posts' but ignore that. It is a direct link to communicate with the moderators. Just ask them to join your two threads together.

Threads merged

Are you planning to stop in Manchester,VT or NH? In any case I would not bother with stopping in New Haven unless something at Yale interests you.

There Is a lot to see between Portland and Boston, Portsmouth NH, Rockport, Ma, Salem MA etc

Day 1 & 2 I would just stay in Chatham instead of changing hotels. Provincetown is only a 50 min drive, you could easily do an all-day trip on day two. Enjoy Chatham and surrounds on day one.

I assume you're detouring up to Manchester VERMONT since you say that it is a long drive to Lake Winniepesaukee? Bayside Inn is a nice place to stay at Lake Winnie.

With all that car time and so many one-night-stops/changes of hotel, I think you'll finally be more than ready to settle in somewhere for for 3 nights , so a spot in or near Portland sounds good. In-town Portland if you're foodies who want to check out the restaurant scene....or outside of Portland along the coast if you're more interested in beach time and relaxation. From Portland you can visit Freeport shopping outlets and (same day) Wolfe's Neck Park. Day 2 Fort Williams and Cape Elizabeth/ Two Lights....with a drive around to Higgins Beach and Scarborough Beach/ Pine Point with maybe a walk from Pine Point to Old Orchard along the 6 miles long beach which will be quiet at that time of year. Other day trip possibiliites include the glorious Sebago Lakes Region, or south to classic touristy villages Kennebunkport and Ogunquit and the Wells Preserve,

Thank you oldemalloy and clarkgriswold your input is really useful.

We have for a few reasons booked first 3 nights in Chatham sot hat ties in with your suggestion.

Manchester is VT yes and we wont bother to stop in NHaven as I think there are places we'd rather see.

Would you think it best to stay in Falmouth 1 night or 2 in Newport?

Agree with having a few nights after all the stops.

I will check out the other places you've suggested.

Would you think Bar Harbor is too much to do? we would love ot go but have kind of discounted it due to the extra driving.

Thank you all again - so excited to come now.

Unfortunately I think Bar Harbor requires too much driving time and I95 is very boring. We liked the mailboat trip around Portland's Casco Bay which canhave you back in the old Port area by lunch time if you do a morning ride. We have not been on an evening cruise. Agree lots of great food opportunities in Portland. You may want to sit a bit in Fort Williams Park for great view of Casco Bay. Get a lobster roll from Bite Into ME food truck if it's still there that time of year.
i'm not a fan of southern Maine although for evening entertainment the Ogunquit Playhouse can be very good. If you choose day drives from Portland I would head north where things are more rustic. It would be a long drive from Portland but auto road up Mt Battie ends with terrific view of ocean and Camden Harbor, Several windjammers have home port there. Keep in mind south of Portland is touristy. North of Portland you have a chance of seeing quieter towns. Rockland is an industrial port but is also home to the Farnsworth Art Museum and the Owls Head Transportation Museum. If it,s a weekend there could be special event going on. Great fun when they have antique airplanes flying.
there's no chance of getting a reservation at the Lost Kitchen but their story is filmed on the Magnolia Network.
Depending on what you want to do in Portland area you might consider staying further north.

Yes I agree - you've confirmed our thoughts - we will just have to accept that BH is too far on this occasion. Always good to have something to come back for right!

I guess my slight concern with Portland is that to do anything south and stay in Portland we will be doubling back on ourselves as ultimately we will be driving back into Boston on that route.

Thank you for you help.

Admittedly I haven't read all the posts in detail but I can comment on the Maine/Portland part of your itinerary because its my stomping ground. Count on a min of 3.5 hours from Mt. Washington to Portland, allowing for a photo op or two along the way. Bar Harbor/Acadia is 3.5 hours from Portland if you take 95 and not the scenic route. I agree with not trying to fit it in on this trip; however, there are other interesting towns within an hour or two north of Portland - Rockland (Farnsworth art museum with lots of Wyeths), Damarascotta (oyster aquaculture mecca), Camden - charming small town with schooners and a state park with a drive up to a nice little mountain vista. Beautiful that time of year. Foliage is typically peak the first 2 weeks of October here, which means that it is crowded and you'll need reservations ahead. I might recommend a night in the Camden/Rockland area. I'd plan 4 hours drive from Rockland to Logan Airport to be safe, so you could do that your last day. (usually flights across the pond are late afternoon/evening)

I'm getting out of order here, but before you headed up to Camden/Rockland you could spend 2 nights in Portland. Our little city is becoming quite popular, a real foodie town. Tons to do - great art museum, shopping, crafts, craft breweries galore (even a Brit will be impressed with our beers. Our Belgian friends sure were!) Take a ferry/boat tour around the harbor, drive over to Cape Elizabeth to see two lighthouses.

Or, if you prefer not to go further north than Portland, spend a night in Ogunquit - a beautiful beach and art mecca. Let us know a little more about what you like to do and we can be more specific. Rocky coast or beaches? History? Art? Food? Although the beaches you'll see on the Cape are beautiful.
https://cimg3.ibsrv.net/gimg/www.fod...a7f3d1d352.jpg

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.