Brattleboro, located ten miles from the Massachusetts border, is the second largest town in Vermont. The parking lot at Harmony Place is a great hang-out spot where folks loiter all day; a ride to the outskirts of town might be found here.
There is a decent music scene to be found amid the various bars and basements of Brattleboro, and people are more than friendly with a laid back often hippy approach to life. There is often a decent amount of travelling kids to be found in the town given the nearby railroad tracks and Brattleboros reputation as a safe haven for travelers of all kind.
To go north, walk or take the Bee Line shuttle to the traffic circle at the north of town; hitch from the I-91 entrance (#3).
To go west toward Bennington, walk out Highway 9 until you reach I-91. Just over the freeway there is a nice shoulder to hitch on. You could be lucky and get a ride straight through, but much of the traffic on Highway 9 is somewhat local, so it may take two hitches to reach Bennington, three or four for Albany, NY (beware!).