West of Brattleboro, Route 9 winds like a salamander through the southernmost peaks of the Green Mountains, dipping into creek beds forested with birch, beech, and sugar maple, and rising for stunning views of the surrounding hills. (The summit of Hogback Mountain is particularly worth pulling over for.)

The small college town of Marlboro is little more than a blip on the map, consisting of a few old farmhouses gathered around an old town hall. That changes every summer, however, when it becomes home to a renowned classical music festival.

Halfway between Brattleboro and Bennington, the unpretentious town of Wilmington has more worth stopping for. Unlike the ultra-quaint villages and overdeveloped ski resorts that surround it, Wilmington feels like the real deal, owing its atmosphere more to a 1950s-era vision of main street than the backwoods colonialism that pervades the rest of the region. Along the trail, an overflow of artists and craftspeople from Brattleboro fill the hills with galleries and scattered studios.