Brattleboro: 105 miles NW of Boston; 148 miles SE of Burlington
The southern Green Mountains are New England writ large. If you've developed a notion of what New England looks like but haven't been there yet, this may be the sort of place you're thinking of -- small villages in valleys flanked by steep and leafy hillsides, white clapboard inns, and diners where the men all wear Red Sox caps and stop talking when you walk in the door.
The hills and valleys around the bustling town of Brattleboro, in Vermont's southeast corner, have some of the state's best-hidden treasures. Driving along the main valley floors -- on roads along the West or Connecticut rivers, or on Route 100 -- tends to be only moderately interesting. To really soak up the region's flavor, then, turn off the main roads and wander up and over rolling ridges into the narrow folds of mountains hiding peaceful villages. If it looks as though the landscape hasn't changed all that much in the past 2 centuries, you're right. It really hasn't.
This region is well known for its pristine and historic villages. You can't help stumbling across them as you explore, and no matter how many other people have found them before you, you'll often feel they're your own discoveries. A good strategy is to stop for a spell in Brattleboro, to stock up on supplies or sample some local food or music. Then set off into the mountains, settle into a remote inn, and continue exploring by foot or bike. In winter, you can even tour the snowy hills on cross-country skis or snowshoes.
Set in a scenic river valley, the commercial town of Brattleboro is more than just a wide place in the road to fill the gas tank and stock up on provisions (though some parts of town do lend themselves only to that). In fact, it has a funky, slightly dated charm; the rough brick texture of this compact, hilly city has aged nicely, its flavor different from that of other Vermont towns due to a suspiciously high concentration of ex-flower children who moved here, grew up, cut their hair, and settled in. They now operate many local enterprises and institutions -- some with a New Age-y tinge.
Brattleboro was actually Vermont's first permanent settlement. (The first attempt at settlement, short-lived, was at Isle La Motte on Lake Champlain in 1666, but it didn't take.) Soldiers protecting the Massachusetts town of Northfield built an outpost in 1724 at Fort Dummer, about 1 1/2 miles south of the current downtown -- the site of the fort is now a small state park with a campground -- and Brattleboro soon became a local center of trade and manufacturing. One of the companies here was the Estey Organ Co., which once supplied countless home organs, carved in ornate Victorian style, to families across the nation.
Brattleboro is still the commercial hub of southeastern Vermont, positioned at the strategic junction of Interstate 89, Vermont state highway 5 and 9, and the Connecticut River. It's the most convenient jumping-off point for those arriving from the south via the interstate. If you're looking for supplies, you'll find a strip-mall area of big grocery stores, gas stations, and chain restaurants located just north of the city center on Route 5 (the main street) near the traffic circle connecting with Route 9. For more interesting shopping, though, take the time to explore downtown's nooks and crannies.
Brattleboro has long seemed immune to the vexations of modern life, but one modern inconvenience has made a belated appearance: traffic. Lower Main Street, near one of the bridges from New Hampshire, can back up in the direction of town, leading to a bit of un-Vermontlike horn-honking. But life here is mostly tranquil and neighborly.