Roadtrip through Bennington, Brattleboro, and Chesterfield

If you’re looking to take a nice cruise and peep at the foliage through three states, look no further— I’ve got a plan for you. Take Route 7 from Troy towards Bennington, Vermont. Check out the moose and cougar statues along the way.


Grab some breakfast at the Blue Benn Diner. This is a sweet little dining car with some great breakfast. I had their pumpkin pancakes which were pretty phenomenal. Head east on Route 9 towards Brattleboro, Vermont. This town has some quintessential New England charm.

1383148_10202230383739004_1548382665_n Grab a cup of something warm or a snack and enjoy shopping about the main street. Don’t forget to stop in Mystery on Main Street, an interesting independent bookstore that has a lot of mystery novels. Great to get in the Halloween spirit! Hop right over the state line into Chesterfield, New Hampshire. For a great hike visit Madame Sherri forest. This is a fascinating and stunning place. There is some interesting history here about Madame Sherri, a 1920s Parisian costume designer. The amazing ruins of her home are in the forest, and among them you can climb up a great stairway leading to nowhere.


There is an enjoyable two mile trail leading to a summit with spectacular views.


Take a leisurely drive to NY, maybe stop at Man of Kent for some great pub food.

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1 Response to Roadtrip through Bennington, Brattleboro, and Chesterfield

  1. David Fiske says:

    For the complete scoop on Madame Sherri, see the book I wrote with Eric Stanway: Madame Sherri – The Special Edition.

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