frogster

My partner and I are currently planning our big road trip through the northeast for the second half of May.
Currently we've scheduled ~7 days for the New England part of the route which will take us from from Montreal to New York.
Our general thinking is to drive via Mt. Washington to Portland (maybe even further up north to Bar Harbor), down to Boston and from there via Long Island into New York.
We�ll definitely want to do some whale watching along the way, stop often for seafood and visit Salem, Concord MA. & the USS Constitution.

What stops would you recommend (besides Boston which is a given)?
Any must sees / dos for us?

AMflier

Be wary of spending more time in the car driving than out of the car actually seeing something. Also note that the weekend of 27-29 May is a long holiday weekend in the states and that traffic will be very heavy,
What are you interested in seeing?

Blumie

I would spend a day or two in each of Burlington and Stowe, then a quick (maybe 2-3 hours) stop in Montpelier (where I�m a fan of Three Penny Taproom for a meal). Another several hours, perhaps an overnight, checking out Woodstock, VT before a meal at Simon Pearce (I prefer lunch over dinner, but both are good), followed by 20 minutes checking out the beautiful Quechee Gorge. At that point I might drive straight through to Boston, perhaps checking out Concord, MA and Walden Pond on the way.

StAugustine

Bar Harbor and Acadia State Park is a great place to visit. But be aware that it is quite far north...about 3 hours from Portland.
As for a whale watch, if you are going to Salem there are several excellent whale watches in Gloucester, right nearby. We went on 7 Seas a couple of years ago.

Out of my Element

There is a good Road Trips Forum over at TripAdvisor that you might want to also post on

djp98374

im a DE on road trips forum on TA

its best to have an idea of your full trip plan to then have some balance on what youwant to do and the places you see.


if youwant to do Acadia

day 1-2 drive to bar harbor. Night in central New Hampshire
day 3 Acadia
day 4 to portland
day 5-7 your drive to nyc with a stop to do sea life watching. I don�t know where is a good location on the New England coast for it.

galeaoguy

Take a look at entering the US in Newport VT. From there to St Johnsbury VT, where heading East on rt 2 you can find yourself quite near Mt Washington having to head south on route 16 (Gorham NH), which goes right past Mt Washington.. from that point, after enjoying that area finding (find Conway, rt 112 (Kancamagus Highway- a great drive!) to Lincoln NH ) and driving south on rt 93 will take you toward Boston. You could either go into the city for the day (The Freedom Trail is a good thing and includes Old Ironsides..), or find your way to Salem and Gloucester either choice should offer opportunities for Whale watching, but I think Gloucester would work better. From that, a drive to New London CT will get you to a ferry that goes to Long Island, where you could drive the length of Long Island into the city..

anyway some food for thought.. I'm sorry to say, driving to Acadia National Park would be very time consuming, although it's one of the more beautiful places I have ever visited (many times)

pstm91

I have done this trip many, many times and I agree with the others - save Acadia for another trip. It is way out of your way and you'd really want to spend at least 2 full days there to explore the park and do real hikes, which would not give you much time at all to make stops along the rest of your way down. Also, the drive from Maine to NY will just be highways, mostly I-95, with some opportunities to take side roads. While it's a nice ferry ride from CT or RI to Long Island, the drive through Long Island to the city is not remotely scenic. I'd also be hesitant to recommend whale watching- May is the very beginning of the season, so odds are not in your favor to see anything.
The drive from Montreal down through either VT or upstate NY is much more scenic, especially as you get down towards the Hudson Valley. Straight down NY is by far my favorite way to do the drive - it's the most direct, most scenic, and there are lots of places to stop along the way. Since seafood seems to important to you, there are tons of fantastic restaurants along the Hudson, especially once you are south of Albany and get to towns like Hudson, Rhinebeck, Saugerties, Kingston, etc. Bear Mountain and West Point are also very much worth a stop.
You seem quite set on Boston, in which case I strongly recommend cutting through VT and NH rather than going way out of your way to Maine. You'd be coming into Boston via the north, and it is definitely worth exploring the north shore towns for a bit - Marblehead, Salem, etc. I'd then make stops in RI and along CT, such as Newport, Westerly, Stonington, Old Saybrook/Old Lyme, Stamford/Greenwich, and then into the city.