You could easily breeze through southern Vermont in a couple of days, but to really appreciate the area, a leisurely week of cruising the back roads or the ski slopes is more like it. Unlike the more northerly parts of the state, lodgings and restaurants in this area tend to stay open year-round, making it a nice place to visit in the winter (though be warned that the whole area shuts down during the month of March, otherwise known in these parts as “mud season”). Of course, the region really comes into its own in fall, when the foliage does its annual color dance on the back roads, and country inns often jack up their prices as well.

You’re best off basing yourself in Brattleboro, the pint-sized cultural mecca that beguiles tourists. Try to time your trip to take in the monthly Gallery Walk on the first Friday of the month, when the town really displays its artistic talents. While in Brattleboro, you can take a few leisurely days to explore the nearby maple syrup farms, the cheesemaking operation at Grafton Village Cheese Company, and the quintessentially Vermont Vermont Country Store.

Unlike Brattleboro, there’s not much to see in downbeat Bennington, but it’s worth making a daytrip to the city to see the Revolutionary War–era Bennington Battle Monument and its accompanying museum. For many shopaholic weekend visitors, a trip to the region begins, stays, and ends in Manchester. Full days of shopping at deeply discounted designer outlets and luxury inns have made the place a destination that can easily fill an enthusiast’s vacation.

North of the Green Mountain National Forest, you could easily spend another couple of days along Route 4, starting in Woodstock. Nearby, plan to stop by the underrated Vermont Institute of Natural Science for a bit of a walk on the wild side. Farther west, Killington Resort, the biggest, baddest mountain in New England and a must-ski for any serious enthusiast, and the city of Rutland is worth a detour for its many covered bridges and the irresistible lure of the New England Maple Museum.