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Drive in today from NYC. Actually staying in Arlington.

Interests for this trip are hikes, historical landmarks, sightseeing, eating and drinking.

On the drive there, or back, I would go through Stockbridge, MA and take highway 7 to Arlington. Or, you could make a day trip to these places if you have time. It's 1 1/2 hours from Arlington, VT to Stockbridge.

Stockbridge, Lenox and Lee are three towns that are about 10 miles apart.
The Norman Rockwell museum and studio are in Stockbridge; we did the museum but not the studio. Took about 2 hours.
Tanglewood is at Lenox; that where the Boston Symphony does the Boston Pops but you can walk around the grounds for free. They may be having concerts this weekend and that's not free.
All three of those towns have a variety of restaurants. The Red Lion Inn is a well know one in Stockbridge; we didn't eat there as the town was crowded when we were there.

North of there is Pittsfield which is a larger town/city. The Hancock Shaker Village is just out of Pittsfield. It was a working farm but now it's a farm museum I guess. It's interesting because of their lifestyle and creativeness. If you go there catch some of the talks by the employees/volunteers.

North of there is Mount Greylock and MG State Reservation. We didn't go there but you can drive to the summit of MG or hike. The hike is strenuous according to their website.

Then North Adams, which is almost to VT, is supposed to be a good place to visit; it has art galleries, museums, hiking and breweries. The Mass Museum of Contemporary Art is the largest contemporary art museum in N. America.

Just outside of Arlington is Robert Frost's home. We drove by it but didn't stop; not sure it was open.

Bennington has locally owned restaurants on Main Street.

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N. Rockwell museum.

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Shaker village. There are not many Shakers left because they were celibate. IIRC the women lived in the that large brick building on the left; not sure where the men lived.