Vermont State Route 30 runs from the northwestern part of the county to the southeastern part of the county. It goes from the Bennington/Windham County Line to Brattleboro. VT St Rt 30 passes through the following towns in Windham County. Rawsonville Jamaica West Townshend Townshend Harmonyville Newfane West Dummerston Brattleboro VT St Rt 30 is multi-plexed in Windham County. Vermont State Route 100, from Rawsonville to Jamaica. VT St Rt 100 crosses the following highways in Windham County. Vermont State Route 100, at Rawsonville. Vermont State Route 100, at Jamaica. Vermont State Route 35, at Townshend. Interstate 91, at Brattleboro. (NO Interchange) U.S. Rt. 5, at Brattleboro. Vermont State Route 9, at Brattleboro.
