Molly Stark Trail · VT-9

The southern Vermont crossing on VT-9, the Molly Stark Trail: you leave Brattleboro, climb through Marlboro to the Hogback Mountain overlook, drop into Wilmington and cross the range through Searsburg and Woodford to Bennington. It's 40 miles of long climbs and open bends, with the best view right at Hogback. It's the region's main east-west road, so expect trucks and seasonal traffic. Stop in Wilmington, halfway across.

VT-9 is called the Molly Stark Trail along its whole length, after the wife of General John Stark, and it follows the general line of his march home after the Battle of Bennington on August 16, 1777. Before the battle he is said to have told his men that the flag would fly over the hill by nightfall "or Molly Stark sleeps a widow." Wilmington keeps a statue of her downtown, and Molly Stark State Park, just east of the village, has a trail to the Mount Olga fire tower.

The highlight is the Hogback Mountain overlook in Marlboro: from the deck on the south side of the road, on a clear day, the view runs about 100 miles over Vermont, Massachusetts and New Hampshire, with Mount Monadnock to the east. Hogback was a ski area until 1986 and the land is now conserved. In Bennington the route ends on Main Street, where VTrans replaced the VT-9 bridge over the Walloomsac in 2026, so check for detours before you go. There's fuel in Brattleboro, Wilmington and Bennington.