The easy access to the southern part of Vermont means that license plates from New York  and Massachusetts  often outnumber the green-and-white plates of the locals. The winding roads of the Green Mountain  foothills can get especially crowded on weekends around foliage season (mid-Sept.–mid-Oct.) and during school vacations in ski season. Why go farther north, skiers ask, when mountains like Stratton, Mount Snow, and Okemo offer challenging trails just a couple hours’ drive from Boston?
The three major towns of southern Vermont each have their own distinctive personalities. Brattleboro  exudes an artsy, crunchy-granola vibe that wafts from galleries and shops readymade for browsing. Bennington  is a working-class town living off its history as the site of a major battle during the Revolutionary War. Manchester , on the other hand, is anything but struggling. Buoyed by its designer clothing outlets and luxury spas, this is where the New York  set comes to get away and play.
In between these relative metropolises are the story-book villages that epitomize New England in the minds of many people. One of the best ways to see this part of the state is just to get in the car and drive. You are sure to come across that perfect gazebo on the town green; that country store packed with homemade fudge and handicrafts; or that maple syrup farm offering tours with the purchase of a jug.
North of Manchester , Route 4 cuts across the center of the state like a belt tied tight around its waist, serving as a physical and mental dividing line between northern and southern Vermont and connecting some of the state’s prime attractions, including the sophisticated little village of Woodstock , the skiers mecca of Killington  and riot of restaurants and motels climbing up to the peak, and Rutland , which used to be one of Vermont’s most populous cities in the 19th century, but has since seen better days. Scratch beneath the rust, however, and you’ll find a gorgeous Victorian downtown, surrounded by several stop-worthy tourist attractions in the surrounding valley.