Bennington: 143 miles NW of Boston; 126 miles S of Burlington. Manchester: 24 miles N of Bennington.
Southwestern Vermont is the turf of Ethan Allen, Robert Frost, Grandma Moses, and Norman Rockwell -- some pretty heavy hitters, Americana-wise. It may thus seem familiar even if you've never been here before now. Over the decades, this region has subtly managed to work itself deep into America's cultural consciousness, identity, and sense of wistful nostalgia about the past.
The region is sandwiched between the Green Mountains to the east and the rolling hills along the Vermont-New York border to the west. If you're coming from Albany or the southwest, the first town you're likely to hit is Bennington -- a commercial center that offers up low-key diversions for residents and tourists alike. Northward toward Rutland, the terrain is more intimate than intimidating, with the towns clustered in broad and gentle valleys along rivers and streams. Former 19th-century summer colonies and erstwhile lumber and marble towns exist side by side, offering pleasant accommodations, good food, and -- in the case of Manchester Center, at least -- pretty good big-brand-name outlet shopping.
Interestingly, southern Vermont's sprouts of sophisticated culture (the outlet shops, the ski resorts, the fancy inns) are within easy striking distance of the Green Mountains, enabling you to both enjoy the outdoors by day and goose-down duvets by night. (As a bonus, shuttle buses now cruise the southern mountains, all touching base in Manchester during their perambulations.) This region attracts its share of weekend celebrities, shoppers, gourmands, and those simply looking for a brief and relaxing detour to the elegant inns and B&Bs for which the region is so widely known.
Bennington, Vermont's third-largest city, owes its fame (such as it is) to a handful of eponymous moments, places, and things: the Battle of Bennington, fought in 1777 during the American War of Independence; Bennington College, a small, prestigious liberal arts school; and Bennington pottery, which traces its ancestry back to the original factory in 1793 and is still prized by collectors for its superb quality.
Today visitors will find a Bennington of two faces. Historic Bennington (more commonly known as Old Bennington), with its white clapboard homes, sits atop a hill west of town off Route 9; look for the mini-Washington Monument obelisk and you're there. It's a gem of a neighborhood, particularly if you fancy old homes and additional cows, and views materialize as you continue uphill and west from here on Route 7. The surrounding countryside, though defined by rolling hills, has fewer abrupt inclines and slopes than many other parts of Vermont, so go backroading for a bit if you can.
Modern downtown Bennington, on the other hand, is a pleasant but no-frills commercial center stocked with real estate offices, plumbers, diners, and stores that still sell what people actually need -- not so much a tourist destination as a handy supply depot. This downtown is compact, low, and handsome, boasting a fair number of architecturally striking buildings. In particular, don't miss the stern marble Federal building (formerly the town post office) with its six fluted columns at 118 South St.