Wilmington was a village flooded twice, once by water on purpose and once by water on its own. In the 1920s, a dam on the Deerfield River created the Harriman Reservoir to the south, also known as Lake Whitingham, one of the largest lakes in Vermont, drowning a stretch of farmland and the old village of Mountain Mills. And in August 2011, Tropical Storm Irene sent the river over its banks and through the middle of the downtown, wrecking shops and houses that had been standing for a century and a half. The town rebuilt, and today you would hardly know, though the high-water marks are a talking point.
It sits at the junction of two of the best roads in southern Vermont, Route 9, the Molly Stark Trail, and Route 100, which runs the length of the state along the spine of the Green Mountains. The downtown is a classic New England main street of brick and clapboard buildings, with a general store, cafes, antique shops and a historic inn, and the whole place has a comfortable, lived-in look. Mount Snow, the big ski area, is a short drive to the north, so in winter the town fills up with skiers.
For a rider, it is a base with options. Route 9 runs east and west, with long climbs and descents, and Route 100 runs north along the Deerfield valley with long, flowing bends and wooded hills. Both are well surfaced and popular, so expect company on summer weekends. There are speed limit signs and a state police presence on both. The reservoir, a few kilometres to the south, is surrounded by quieter roads, and the water is a good place for a swim on a hot day. In autumn, peak colour in the first half of October can bring a slow-moving procession of cars.
Wilmington is a good place to stop for fuel, a meal and a rest. The downtown has a number of places to eat, from a bakery and a diner to more ambitious restaurants, and there are stations on the main road. Brattleboro, twenty-six kilometres away, is a bigger town with a lively arts scene and more choices. The best time to arrive is a weekday morning, when the town is quiet and the light on the hills is clear.