Whether you are traveling alone, as a family, or with friends, there are numerous fun things to do in Bennington, Vermont. And whether you seek adventure or somewhere to just cool your head, Bennington is the place.Bennington, Vermont, is just 3.5 hours from New York City. This makes it a convenient place to visit for many city residents looking for a quiet time. Also, it is a small but welcoming town, and that means that life is not as busy as in cities like New York and Boston.