Southern Vermont Weekend

North over the Massachusetts line into the Green Mountains proper: Route 9 across the range, then Route 100 north.

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Why this ride

A one-way ride of 168 km, Williamstown to Jamaica - roughly 3 h 14 in the saddle. The stops in between: Bennington, Searsburg, Wilmington and West Dover. The line favours views over speed.

Roadbook

1. Williamstown start

   Williamstown is the kind of New England college town that looks as if somebody drew it for a calendar: a white-steepled church, a village green, red-brick college halls, and a ring of wooded hills all round. Williams College, founded in 1793, is the heart of it, and the Clark Art Institute, with a fine collection of Impressionist paintings, makes a good rainy-day stop. The town sits in the north-west corner of Massachusetts, a short hop from the Vermont and New York borders, and it is where the Berkshires begin to climb in earnest.

   From here, the riding is some of the best in the north-east. Route 2, the Mohawk Trail, enters the town from the east after crossing the Hoosac Range, and it is among the oldest tourist roads in the country, following an ancient Native American path. The climb to the Whitcomb Summit and the hairpin turn above North Adams are the highlights, with views over the Hoosac valley and tight bends that demand a steady hand. To the south, Mount Greylock, at 1,064 metres the highest point in Massachusetts, has a narrow road to the summit with a war memorial tower on top. The road is usually closed in winter, opening around late May, so check before you go.

   October is the famous month. When the maples go crimson and gold the whole region fills with visitors, traffic slows to a crawl on the Mohawk Trail, and motels book up months ahead. Come on a weekday if you can. Summer is green and warm, with cool mountain air at altitude, and early mornings are quiet and often misty. Watch for frost heaves, gravel after rain and deer at dusk, which are a real hazard on these wooded roads. Moose have returned to the area in recent decades and are best avoided in the dark.

   Williamstown has a population of around four thousand, so it has fuel, a few good cafes, bakeries and a couple of inns. North Adams, about eight kilometres east, is larger and has more, along with MASS MoCA, a huge contemporary art museum housed in old factory buildings, which is worth an hour even for the unconverted. The local craft beer and maple syrup are both good, and a stack of pancakes with real maple syrup is a fine fuel for the climb.

2. Bennington scenic · 210 m

   Bennington is the southwestern gateway to Vermont, a college and craft town of around nine thousand, set in a valley between the Green Mountains and the Taconics. The big thing you see is the Bennington Battle Monument, a tall pale tower of dolomite finished in 1891 that stands on the hill above town and can be seen from miles away. It commemorates the 1777 battle, which was actually fought a few miles west across the line in New York, when American militia defeated a British detachment going after supplies. It is a rare monument you can go up inside, with a lift to the top, and the view across three states is wide.

   The old village on the hill is quieter and more graceful than the downtown below. Old Bennington has a white colonial church with a graveyard where the poet Robert Frost is buried, and his stone carries an epitaph about having had a lover's quarrel with the world. The Bennington Museum holds a large collection of paintings by Grandma Moses, along with local pottery and glass; the town has a long tradition of stoneware making, and the Bennington potters were once a name known across the country.

   The riding is the reason this town sits on so many Vermont routes. Route 9, known here as the Molly Stark Trail, heads east over the Green Mountains toward Brattleboro, climbing past Hogback Mountain, with its long view from the roadside, and twisting through forest on both sides. It is a proper mountain road, with wide bends, steady gradients and a couple of tight spots where trucks come through, and it is a popular ride on any dry day. Route 7A north toward Arlington and Manchester is gentler, with the hills of the Taconic and Green ranges on either side and little villages with covered bridges close by. North Bennington has an old stone railway station and a pretty covered bridge, while Hoosick Falls over the border has the services of a small New York town.

   Fuel and food are easy here, since Bennington is the largest town for some distance, with several stations on Route 7 and Route 9 and a decent selection of restaurants and cafes downtown. Autumn colour peaks around early October, and weekends then can be busy. Spring has mud and the risk of frost, while a clear summer morning is the best time of all to take the road east.

3. Searsburg scenic · 640 m

   Searsburg is a town of a handful of houses on the high plateau of the southern Green Mountains, and it has one claim to fame that stands out against the trees. In the 1990s a row of wind turbines was erected on the ridge above the village, the first utility-scale wind farm in the Northeast, and the white blades, turning slowly above the spruce, are visible from the road. They have been joined in the region by newer, larger machines, but these were the pioneers, and the place feels a little like the start of something.

   The road that passes through is Route 9, called the Molly Stark Trail, and the name is a piece of Revolutionary lore. Molly was the wife of General John Stark, the New Hampshire officer who led his militia against the British at the Battle of Bennington in 1777, and the story goes that he rallied his men by saying that they would win the day or Molly Stark would be a widow that night. They won. The road follows the old route between Bennington and Brattleboro, and the high pass at Hogback Mountain, a little to the east, has one of the finest views in southern Vermont, with the ranges folding away to the horizon.

   Riding it, you feel the altitude, at about six hundred and forty metres, and the cooler air and the dark spruce and fir that replace the hardwoods lower down. The road climbs from Bennington in a series of long, steady bends, with a good surface and plenty of sightlines, and runs along the plateau before dropping toward Wilmington. It is a working road, with trucks and tourists, but it is wide enough to ride comfortably, and the corners are broad and open. Fog collects on the ridge, and in winter the plateau is windy and icy, so be ready for a change in conditions.

   Fuel is the thing to plan, because Searsburg has none. Bennington, eighteen kilometres to the west, is the nearest town of any size, and Wilmington, to the east, has stations and places to eat. There are small campgrounds and a scenic pull-off, but nothing in the way of supplies. September and October are the most colourful months, though midsummer, with the ridge green and cool, is a good time to be above the heat of the valley.

4. Wilmington scenic · 470 m

   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.

5. West Dover scenic

   West Dover sits in a green valley under Mount Snow, and in the summer it is a different place from the ski village it becomes in winter. The mountain was developed in the 1950s by a skiing enthusiast who wanted a big area close to the cities, and it grew into one of the largest in southern Vermont, with a base area, lodges, restaurants and lifts. In the warm months, the hills are green, the lifts are mostly still, and the roads are a pleasure.

   The road that matters is Route 100, which runs through the valley and follows the line of the Green Mountains north for the length of the state. Here it is a smooth, winding road that runs between wooded hills and open meadows, with the Deerfield River nearby and old farmhouses set back from the verge. North of the village, it climbs through forest in broad, gentle curves, and the traffic is light on weekdays. Roads that lead off it, such as the one toward Somerset Reservoir, are narrower and quieter, with gravel patches and a more remote feel.

   The landscape of the Green Mountains was shaped by ancient mountain building and by glaciers, and the soil on the slopes is thin and stony, which is why so many of the hill farms were abandoned in the nineteenth century when farmers headed west. The forests that have taken their place are mixed, with maple, beech and birch in the lower woods and spruce above, and they are among the most colourful in the country in the first two weeks of October. The Long Trail and the Appalachian Trail share a route over the ridge to the north, and hikers often stop in the villages for supplies.

   West Dover has a few restaurants, a general store and small inns, but fuel is a different matter. The village of Dover, a few kilometres away, has the basics, and Wilmington, ten kilometres off, has more, so fill up there before you head north into the mountains. Brattleboro is the larger town to the south-east. In winter, the road is plowed and well maintained, though ice is a hazard, and summer weekends bring occasional crowds for festivals.

6. Jamaica finish

   The route ends here after 168 km.

Where this sits

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