Wow- that sounds like a Fantastic road trip!
When do you plan to go? I hope it is soon, because that whole area has jaw dropping Autumn colors! They should be at peak color over this next two weeks. Bennington isn't far from Albany, where we used to live, so we popped over for day trips a few times.
There are a lot of fun ways to spend your time - especially if you like eating and shopping. The town is full of great little shops. And if you like great specialty beer, the Madison Brewery is a wonderful restaurant. Make sure you go somewhere for breakfast that serves pancakes or waffles with real maple syrup. I just had to look this up, because I couldn't remember the name of this one place that is in a real, authentic old diner car (made from a train car) it's called the Blue Benn Diner. Here is a really good description of it:
http://www.roadfood.com/Restaurant/R...lue-benn-diner
it is fun to eat there, but gets crowded during peak mealtimes.
The Bennington Museum is terrific. Is that where the Dear Jane Exhibit is? The museum has a large amount devoted to the American Revolution, but also a section of real Grandma Moses paintings. And the nature trail there is very beautiful.
They often have painted Mooses (is that the plural of Moose?) all over town that are really fun to see how each artist did them up.
The first thing you see in Bennington is the battle monument. You can go up into the top and look at the surrounding mountains. Just a gorgeous area!
you'll have a ball!