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Help with north and west of Boston part of trip!

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Help with north and west of Boston part of trip!

Hi there fellow travelers,

My husband and I are heading to New England for 2 weeks from May 17 to June 1. The second week we have figured the broad plan out (southern New England, Newport, Cape Cod, islands and Boston) and have all our accommodation sorted out.

I need some help and advice for the first week of the trip. I have a rough idea of what we want to see but not sure how to space it out in terms of how much driving is easily manageable in a day and still getting to do stuff.

We have from Saturday May 17 to Friday May 23 to get from Boston to Ridgefield CT (where we have family).

The rough plan is:

Arrive Boston - drive to Bar Harbor, sightsee along the way - stay 2 nights there

4 nights: driving over to White Mtns - move through NH, come south through Vermont, maybe parts of northern Mass, Berkshires, Green Mtns and finish up at Ridgefield.

I would love to see Lexington/Concord - not sure how to fit this in.

As you can see this part of trip I'm not so sure how to break it up. What would be good places to break up the trip, places to see.

We want to sightsee, do some light hiking, cultural/historical, off the beaten track stops.

We are not so much interested in cities or shopping or nightlife for this part of trip.

I have my guidebooks, I am reading other people's experiences on the forum but would also love any input or advice people who know this beautiful part of the world may have. It all seems so scenic that it's hard to pick out a clear route.

Thanks so much,

A and M.

Destination Expert
for New England
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6,166 posts
189 reviews
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1. Re: Help with north and west of Boston part of trip!

Hi - Looks like you have a good start. If you want to see Lexington and Concord, I would probably do that first, before heading up to Bar Harbor. You won't have time to see it all, but you can get a taste. You can head out of Boston early and spend until mid afternoon touring the Concord area, then hop on 95 and head north. Bar Harbor is about a 5 hour drive from Concord. I would pick a base in NH for 2 nights. Jackson, NH is a very popular resort town for touring the White Mountains. I might then either pick another base in VT for 2 nights, or do 1 night in VT and then 1 night in the Berkshires on the way to Ridgefield. Look at Woodstock or Grafton, VT, two picturesque VT towns. On your way down 91 into MA, you might look at Northampton, MA, a college town with great restaurants and shops, as a western MA stop convenient to the highway on your way south to Ridgefield.

2. Re: Help with north and west of Boston part of trip!

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