Vermont State Route 8 is a north-south highway in Southwestern Bennington County. It runs from the Massachusetts/Vermont State Line to Vermont State Route 9. Over half the highway is multi-plexed with Vermont State Route 100. They runs together from the Massachusetts/Vermont State Line, to Heartwellville. VT St Rt 8 passes through the following towns in Bennington County. Stamford Heartwellville Searsburg VT St Rt 8 is multi-plexed in Bennington County. Vermont State Route 100, from the Massacusetts/Vermont State Line to Heartwellville. VT St Rt 8 intersects the following highways in Bennington County. Vermont State Route 100, at Heartwellville. Vermont State Route 9, at Searsburg.