The trip begins about 2 ½ hours from Boston, 16 miles west of Brattleboro, where Route 9 west descends into the crossroads town of Wilmington. Simply driving Route 100 from here to Waitsfield, with no stops, would take only a few hours. But antiques shops, waterfalls, hiking trails, and farm stands can easily stretch the trip over two days and nights.
After the sparse settlements preceding it, Wilmington feels like a hospitable Victorian parlor. The Deerfield River flows through the middle of town, and flowerboxes line the bridge. Next to the river, an artful arbor shelters a deck beside a little garden. Beyond, on Route 9, the Crafts Inn sprawls like an overstuffed armchair opposite the white-pillared Vermont House Tavern and the Art Moderne neon of Dot’s Restaurant. Other eateries, galleries, and shops line both sides of Route 9, inviting travelers to stretch their legs, grab lunch or a cup of coffee, or stay the night.
At the traffic light after the bridge, Route 100 breaks to the right, climbing steeply to West Dover. Here the settlement thins out and the countryside opens into dairy pastures, the Deerfield River rushing in gravel shallows beside the road. Travelers with young families can take a detour to Adams Family Farm (watch for signs), where children can interact with horses, cows, and other animals. The Deerfield Valley between Dover and West Dover is known as the Mount Snow Valley, after the ski mountain on the outskirts of West Dover, its slopes carved into a green-on-green tracery. For those who want to stop awhile, Equipe Sport/Mountain Riders, on the Mount Snow access road, rents kayaks and mountain bikes.
After passing through a cluster of resort shops, the road swings sharply east through Podunk - really - and trades the Deerfield River for a series of brooks and boggy lowlands beloved by moose. Vermonters keep a watchful eye out in such places, especially at dawn and dusk, when the ungainly ungulates are most active and likely to stray into the road.
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