Bennington is at the intersection of state routes 9 and 7. If you're coming from the south, the nearest interstate access is via the New York Thruway at Albany, about 35 miles away. (But you have to drive through the city of Troy first, which takes time; figure 45 minutes or more from the Thruway to downtown Bennington.) From the east, I-91 is about 40 miles away at Brattleboro.
7 Up: Choosing Your Route -- When driving through southern Vermont, remember that there are two Route 7s. Running high along the foothills is the newer Route 7, with its limited access and (in places) double lanes, enabling a speedy and scenic trip up the valley toward Rutland. It passes through a range of absolutely empty foothills (I challenge you to spot a person or even a cow from your car), offering some of the best foliage views you'll ever find on a speedway; there are pull-off areas to take the photos I know you'll want to take. The drawback? There are only a few exits onto and off this highway; you might miss something in between. But if you're in a hurry -- or want to take in expansive views of foliage without any buildings in the background -- take this route.
Meandering along the valley floor, on the other hand, is Route 7A (in slightly pretentious fashion, it's usually called Historic Route 7A). This road is a much more leisurely ride -- you'll encounter lots of locals, and some stopping-and-waiting in the village centers -- with plenty of diversions along the way, including antiques shops, outlet stores, farm stands, historic buildings and inns, and a covered bridge. Both are nice. Choose according to your mood.
The Bennington Area Chamber of Commerce, 100 Veterans Memorial Dr. (tel. 800/229-0252 or 802/447-3311; www.bennington.com), maintains a visitor center on Route 7 about 1 mile north of the downtown, near the veterans' complex and a small park. This office is open Monday to Friday from 9am to 5pm year-round, and also Saturday and Sunday from 10am to 4pm from mid-May until mid-October. There's also a downtown welcome center (tel. 802/442-5758) in a former blacksmith shop at South and Elm streets; look for the big blue flag. Operated by the other BBC -- the Better Bennington Corporation, of course -- it's open Monday through Saturday from 9am to 5pm year-round and has a big map of the area to orient you.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.