The byway is named after the popular wife of General John Stark, who led the Colonial militia to a victory at the Battle of Bennington on August 16, 1777. The Molly Stark Byway travels around and through Green Mountain National Forest and its towns and villages. Interesting, must-see towns on the byway are Brattleboro, Bennington, and Wilmington. The scenic byway passes historic districts, hiking trails, state parks, winter sports centers, and lakes. It is a compact taste of mountainous southern Vermont.
Tucked between the Taconic Mountains and Green Mountains, along Route 7A, the Shires of Vermont is a place of majestic mountain views, brilliant fall foliage, and wonderful towns, including the bookend towns of Bennington and Manchester. Historic Route 7A runs parallel to the Long Trail, a hiker’s path that follows the length of Vermont from Massachusetts to Canada; part of the Long Trail also is the Appalachian Trail. Each town of the Shires has its own ambiance. Pownal has organic farms against a backdrop of mountains. Bennington is a pretty place with interesting dining and shopping. Old Bennington is the home of the Bennington Battle Monument and it is filled with traditional New England architecture. Manchester, a four-season destination, is known today for golf, fishing, skiing, the arts, and shopping. Distance from Pownal to Manchester is 33 miles – an easy distance that allows for a lot of stopping and sightseeing along the way