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 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 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 the ski resort, it quickly becomes 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 certainly isn't dense (this is not North Conway), the buildings represent an unsavory mélange of architectural styles, the most prominent of which could be called Tyrolean Chicken Coop. Many of these buildings began as ski lodges and have since become boutiques, inns, and restaurants. The silver lining: Development here prompted Vermont to pass a progressive and restrictive environmental law known as Act 250, which has preserved many other areas from subsequently being blighted by this sort of rapid growth.
When you're driving in the Mount Snow area, remember that you're not restricted to Route 100. The area is packed with smaller roads, both paved and dirt, that make for excellent exploring (if your shock absorbers can handle it; don't go too far off the main roads in a sports car). Be sure to buy a map or DeLorme atlas of Vermont before plunging in, and make sure you've got snow tires on if it's winter. You'll need them.