Route 7 Fun Run

The Berkshires — together with the Green Mountains across the state line in Vermont — form one of the most picturesque regions in the Northeast. Better still, this interstate region is home to one of New England’s best scenic drives, the storied U.S. Route 7.The route begins on the banks of the Connecticut River north of Greenfield. Heading north along the Vermont-New Hampshire border, the route passes the historic mill towns of Brattleboro and Bellows Falls. This region is famous for its many covered bridges, the West Dummerston Covered Bridge serving as a particularly noteworthy example. The route curves west along the Williams River, passing the historic city center of Chester. Heading south along the Green Mountains, the route cuts to the west again along the Molly Stark Trail. Old Bennington and historic Williamstown round out the route before the return trip to Greenfield.