Why this ride
A Green Mountain crossing between two historic valley towns. The road: VT-9 and VT-100. Distance and riding time are estimates from the checkpoints until the road is measured on this page.
CURVESCOUT / MOTORCYCLE RIDE
Molly Stark and Deerfield Valley
Plan this ride
- Recorded distance
- 531 km
- Riding-time estimate
- 8 h 07
- Journey
- Recorded itinerary
Distance and timing basis
The recorded total and the leg detail need reconciliation. Inspect the leg notes before using this record for timing or navigation. Stops, delays, approach and any separate return travel add time. Basis: producer-declared routed record.
Reading history stays on this device. My road watch requires a separate selection; opening it does not subscribe this ride.
Distance and riding time are measured on the routed road. Check local closures and conditions before you ride.
Waypoint introductions and full write-ups
1. Brattleboro
Brattleboro sits in the southeast corner of Vermont, on the Connecticut River, and it is a place with real character, a town of about seven thousand people that feels bigger because of its energy. It was the site of the first permanent English settlement in Vermont, at Fort Dummer, built in 1724 as a frontier defence against raids from the north. The town grew as a trading point on the river, and in the nineteenth century it became known for the Estey Organ Company, which at its peak was one of the largest producers of reed organs in the world, shipping instruments to parlours across America.
2. Stockbridge
The long Main Street runs between old maples and white porches, with the Red Lion Inn, a sprawling clapboard hotel with a rocking-chair porch, anchoring the middle. Norman Rockwell lived and worked here from the 1950s until he died in 1978, and his painting of this very street, wrapped in snow and Christmas lights, is among his best-loved pictures. The museum that carries his name sits on a hillside just outside the village.
3. Marlboro
4. Philmont
5. Bennington
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.
6. Back to Brattleboro
Return visit. Read the place description above.
More motorcycle rides nearby
- Monadnock Villages Loop · 86 km
- Mohawk Trail Western Climb · 69 km
- Mohawk Trail starting at Greenfield · 69 km
- Mohawk Trail · 63 km