Smugglers' Notch gets its name honestly. When President Jefferson's Embargo Act of 1807 closed trade with Canada, Vermonters hauled goods north through this narrow gap in the Green Mountains rather than go without, and a century later the same pass served bootleggers during Prohibition. Jeffersonville sits on the Lamoille River at the northern foot of that pass, a small village of white clapboard houses, a general store feel, and a covered bridge or two within easy riding distance. Mount Mansfield, Vermont's highest peak at 4,393 feet, looms behind it, and the village has long attracted painters and potters who came for the light and stayed for the quiet.
The ride up Route 108 is the reason to be here. Within a few miles of town the road narrows to little more than a lane and a half, hemmed in by cliffs that rise about a thousand feet and by car-sized boulders that have tumbled onto the slopes. Hairpins come close together, there are blind corners where the rock overhangs the tarmac, and the surface can be damp even in July. Take it slowly, stay well within your own side, and expect other riders, cyclists and walkers on the narrow sections. Large trucks and trailers are banned, which keeps the notch intimate. The road closes for winter, usually from about November until late spring, so check before you go.
At the top there is a small parking area with a short trail among the boulders, a few of which have been given names by generations of visitors, and the air is distinctly cooler than in the valley. Down the far side you reach Stowe, a resort town with plenty of cafes, bakeries and shops, and from there Route 100 returns through the Green Mountain valleys.
For practical purposes, Jeffersonville is small, and the best fuel and supplies are at Morrisville, about twelve miles away, so top up before you head into the hills. Local sugar houses sell maple syrup, cheese and cider donuts in season. September and early October bring the famous foliage, along with the traffic, and late spring, once the road has opened, is a good time for empty roads.