The route really depends on which states you want to see. Are you flying into Boston? You might go up the coast of Maine stopping in Portsmouth NH for a harbor cruise and then travel Portland ME to NH's White Mountains. If you stay in the Lake Winnipesaukee area on the northern side of the lake, it's an easy trip to the mountains.
We like the mid-coast area of Maine the best. Portland has an interesting food tour in the Old Port Area. From there you could make day trips to other places like Rockland (about a 2 hour drive north) or south to Ogunquit, return to Portland for dinner (lots of great restaurants) and evening events.

From NH's lakes region you could head over to northern Vermont with a visit to Shelburne Museum and Burlington. Take a day to drive south to Lenox, stopping along the way. Vermont is very rural and so is western Massachusetts where Lenox is located. From there you could return to southern VT or visit Cape Cod.

Perhaps you should list what you already know you want to see so it would be easier for people to think about a route for you.

Welcome to Fodor's! Knowing a little more about you and your trip will help us help you. For starters:
- What are your start and end points? (For example, are you arriving in the area by airplane? If so, where?)
- How many are you? Are there kids (and what ages)?
- In addition to Tanglewood, what are your interests? Mostly arts? US history? Nature? And if nature, do you like to get out and do things like hiking or rafting, or more of sightseeing from a car - more active, or less?
- Is there a part of New England that interests you more? Less? Mountains, coastline, ocean beaches vs. lakeside ones...

With 19 days, you have a nice amount of time to do some exploring.

Here is a list of August events throughout New England. If something interests you, plan your trip to attend.

http://www.discovernewengland.org/new-england-events/august-2012/

I can't do better than dfrostnh's recommendation unless you have special interests or issues. You need to book lodging in the Berkshires as soon as possible.

Hi,
Thanks to everyone for your posts. Sorry for being not too specific:

1. It's our first time in New England, we've been several times in USA but mostly big cities. So evertythin is new for us.
2. We arrive and depart from Boston (we're from Spain)
3. No kids, just the two of us.
4. Our interests are mostly nature, and we like hiking.
5. We're interested in mountains, lakesides, little towns and villages, coastline, ocean beaches. I also love photography.

We already have booked 2 nights at Lenox, but we can add an extra day if necessary, Ackislander.

Our idea was seeing Boston first, from 5th to 7th and depart Boston early on 8th. Then we're not sure if heading to Cape Cod then or go to New Hampshire, Maine and Vermont directly and leave Cape Cod for the days after Lenox (17-18th).

Thanks to all for your inputs and thoughts !!!

Manolo

Great link, Rizzo. How could I forget the NH League of Arts and Crafts Fair in Sunapee. This is not just any craft fair, this is the highest quality juried arts and crafts. It's held at the ski area so you can also take the chair lift to the top for wonderful views.

My current favorite small town in VT is Brandon. Near Brandon is Bristol. From Bristol you can take the route over the mountains to Rt 100. I believe it is called Lincoln Pass. Not too far outside of town is a popular swimming hole on the river. It's very shallow at one point but upstream is a small waterfall and deep pool. Older kids jump off the ledges into the pool. Very nice place to picnic. Wear water shoes if wading, the shallow bottom is very rocky. It's the kind of place some might think doesn't exist any more. We have a river swimming hole in our town, too. Not as dramatic but it also has a large boulder from which kids jump.

Since you like nature, I would also schedule a kayaking trip someplace. It is very popular (although my husband doesn't care for it). A friend took me on the local river. You can beach someplace for lunch. Be lazy. Enjoy seeing different birds. In some places it's possible to see a bald eagle. On others, loons.

My favorite small town in NH is Center Sandwich which is between the mountains and Lake Winnipesaukee. Twice we have seen black bear in this area.

Going to Cape Cod and then north and then west doesn't make sense.

Do Boston, go north, cross through the White Mountains etc as dfrost suggests, arrive early in Lenox and tour the area for the second part of the day and the following, then head east to Cape Cod, finally returning to Boston for your flight home. It makes a giant loop.

Don't rent a car until you are ready to leave Boston. It's comparable to driving in Rome, Paris, or London, and public transportation is good and safe. You might even take the train to Portland, Maine before renting. Then return the car at Logan airport on your return. You can leave the Cape in plenty of time for an afternoon flight and will not have to drive in the city itself, only on well-marked motorways.

To find things that are going on in the area, go to

www.visitnewengland.com

It has happenings in all the states that might cause you to pick a particular route. It is not a large area compared to the west, but planning a route ahead makes sense. You will probably want to get accommodations in Boston, Lenox and Cape Cod ahead of time.

Thanks Manolo, that helps a lot! I agree that a big loop Boston-Maine-NH-VT-western MA would be most efficient.

The following are some suggestions to look into for eastern MA, in geographical order assuming you'll head north from Boston in a rental car:

Historic Lexington and Concord, 20-30 minutes outside of Cambridge off of Route 2. Where some of the first battles of the Revolutionary War were fought, now part of the Minute Man National Park (spans both towns). Much of the park is like a nature reserve, with no new buildings and not much foot traffic.
www.nps.gov/mima/index.htm

On the edge of Concord and Lincoln, Walden Pond is a popular swimming area in the summer; you can walk around the circumference and try to channel Thoreau despite 20th Century encroachments. Lincoln is known for its large tracts of "conservation land", with walking trails throughout.
www.mass.gov/dcr/parks/walden
http://lincolnconservation.org

Salem is farther northeast as you head towards Maine on I-95. The town takes full advantage as the notorious namesake of the Witch Trials (though, perhaps ironically, they actually occurred in a neighboring town). Hawthorne's House of Seven Gables is here, as well as the excellent Peabody Essex Museum:
pem.org/homepage/index.php

Continuing east from Salem, the coastal towns of Manchester-by-the-Sea, Gloucester and Rockport on Cape Ann are quintessential New England fishing villages. (You don't need to go to Maine for good lobster-!)

{From there, travel from Maine into New Hampshire, then Vermont and down to Lenox.}

Leaving Lenox, head east on I-90. Keep in mind that end-of-weekend eastbound traffic will be heavy on a Sunday, especially later in the day and closer to the Boston suburbs. (On the 17th, you shouldn't have too much trouble with Friday traffic since you'll be reaching Lenox from the places - like VT - that the weekenders are trying to get to!)

I would suggest approaching the Cape via Rhode Island - and possibly fit in a slice of that part of New England, too! (Do a google directions from Lenox to Providence to get an idea of the geography; it's about a 2 1/2 hour if the traffic isn't bad.)

You could stop in Providence if you like but IMO by this point, you'll have seen a lot of New England industrial-era architecture. If you do stop, be sure to spend a little time wandering the campuses of Brown University and Rhode Island School of Design up on the hill! Additionally, RI has some great, long bike paths, one of which starts in East Providence and travels towards Newport.

Newport, RI is famous for the Newport Mansions: the "summer cottages" of the rich circa the turn of the last century. I always find it amusing to visit these with European friends, since they are not dissimilar from your average European villa - and much of the interiors were imported from same! However, their original owners were very much a part of American history, so worth a stop if you like. Some of the most famous properties are managed by the Preservation Society: www.newportmansions.org

Newport also has very nice beaches, and lots of restaurants, bars and shops. If you decide to spend the night, try to get a hotel in the town proper; summer parking can be a time-consuming affair! (Look at the hotels on a map, since a number of them will misleadingly call themselves Newport...)

Back on the road towards the Cape, Tiverton, RI is a small detour for some of the best New England ice cream at Gray's: graysicecream.com. Sandwiches and baked goods at the adjacent Provender are also very tasty.

From Tiverton, you can hop on the I-195 interstate to zip to the Cape. If you have time and inclination, take the back roads towards New Bedford. The towns of Tiverton/Little Compton (RI) and Westport and Dartmouth (MA) comprise part of the southcoast area of RI and MA, with some lovely walking trails through the marshes in places like Allen Pond and Slocum River. Or rent kayaks to laze about on the Westport River. With the exception of Horseneck State Beach, the beaches through here are town-run or private, and as a result less crowded than elsewhere. This page has some good links at the bottom:
http://traveltips.usatoday.com/trails-dartmouth-ma-103025.html
http://ospreyseakayak.com/

In Westport's business district, Partners Village Store serves some of the best lobster rolls around! Plus it has cute local products and souvenirs. Closer to the ocean, have a drink overlooking the marina at the Back Eddy.
partnersvillagestore.com
http://thebackeddy.com

Last but not least, once you're back on I-195, New Bedford is a rather gritty former industrial-era small city. However, it's also known as a National Park for its whaling history, and you can get some great Portuguese and Cape Verdean food here! The Whaling Museum is worth a peek if you're in town.
www.nps.gov/nebe/index.htm
whalingmuseum.org

Oh and after all that, can you believe I *still* forgot something I was going to mention??

FYI, on the coast in New England, the ocean water is much warmer south of the Cape than north of it. (The warm waters of the Gulf Stream run from FL up the coast, then veer out at the "elbow" of the Cape and head out to sea.) So if you're planning on dipping your toes in the water, IMO better to do it in RI or southeastern MA (including the Sound side of the Cape).

Hi !

Thank you very much to all of your for your inputs, help and suggestions. I'll keep them in mind when planning the route. Now we have a much better idea of what to do.

Thanks again !!!