High in the hills on a winding mountain highway midway between Bennington and Brattleboro, Wilmington retains its charm as an attractive crossroads village despite its location on two busy roads. Definitely a town for tourists -- for a light bulb or haircut, you're better off in Bennington or Brattleboro -- Wilmington has a nice selection of antiques shops, boutiques, and pizza joints. Except on busy holiday weekends, when it's inundated by visitors driving oversized SUVs, Wilmington feels like a gracious mountain village untroubled by the times.
From Wilmington, the ski resort of Mount Snow/Haystack is easily accessible to the north via Route 100, which is brisk, busy, and close to impassable on sunny weekends in early October. Heading north, you'll first pass through West Dover, an attractive, classic New England town with a prominent steeple and acres of white clapboard.
Between West Dover and Mount Snow, it's evident that developers and entrepreneurs discovered the area in the years following the founding of Mount Snow in 1954. Some regard this stretch of highway as a monument to lack of planning. While development isn't dense (this is no North Conway, New Hampshire), the buildings represent a not-entirely savory mélange of architectural styles, the most prominent of which is Tyrolean Chicken Coop. Many of these buildings began their lives as ski lodges and have since been reincarnated as boutiques, inns, and restaurants. The silver lining is this: The development along here prompted Vermont to pass a progressive and restrictive environmental law called Act 250, which has preserved many other areas from being blighted by too-fast growth. Remember that you're not restricted to Route 100, no matter what anyone tells you. The area is packed with smaller roads, both paved and dirt, that make for excellent exploring. Just be sure to buy a map or DeLorme atlas before plunging in, and make sure you've got snow tires on if it's winter: You'll need them.
