It seems like Field Work Term would be a great for you to check out. We have a 7-week internship program each year where you can go anywhere in the world. If you are interested in theater and want to be in New York City, but you also want the education that Bennington provides, Field Work Term could be a great time to explore those theater opportunities. Here’s a link for some more info: FWT
I am from NYC and go home about once every three weeks, but I love Bennington and the town of Bennington, too. There are some nice shops, a cafe, and some restaurants in town. I think the theater scene exists more within the college campus (Bennington programs— right now we’re working on Angels in America) than the town, in Great Barrington, or in Williamstown (about 30 minutes away). There is one show each term, and the students have a strong role in the productions.