I think Bennington is widely know because of its historical significance especially relating to its place of importance in the Revolutionary War. There are quite a few reminders of its history throughout the town, the most famous of which is surely the Bennington Monument.
Decades ago a thriving middle class was supported by good paying manufacturing jobs. Since the demise of these factories Bennington has struggled to get back on its feet. There is not only much to see in Bennington there is much to hope for.
The Walloomsac Inn 
Hemmings Motor News Gas Station 
Bennington