The Molly Stark Byway winds its way through lowland valleys, historic villages, busy downtowns, and the beautiful Green Mountains. Anchored at either end by the bustling historic and cultural centers of Brattleboro and Bennington, the Route 9 corridor crosses the heart of southern Vermont for 48 miles.

From the rich farmland west of Bennington, to the famous three-state-overlook at Hogback Mountain, to covered bridges, the Molly Stark Byway follows the general footsteps of an old turnpike across the spine of Vermont. The Byway rings with legendary Vermont names like General John Stark, Ethan Allen, Robert Frost, and Grandma Moses. It passes famous monuments, unique settlements like Woodford (the highest village in Vermont at 2,215 feet), and important historic districts in Brattleboro, Wilmington, and Bennington.

The modern popularity of Route 9 dates back to the dawn of the automobile age with the beginning of "pleasure driving" when in 1907 an ambitious hotel owner came up with the concept of the "Ideal Tour" through the hill country of New England, guaranteeing to auto travelers "A First Class Hotel at the End of Each Day's Run."

It is thought the Molly Stark Trail once included The Great Albany Road, built in 1746 and used for the transportation of military patrols and supplies, which ran from Fort Dummer (1724) outside of Brattleboro, Vermont, to Fort Massachusetts, in North Adams, Massachusetts (1746). The Western Extension of the Great Albany Road was built in 1762 to link Wilmington with Bennington, creating the first pass over the Green Mountains and uniting Eastern and Western Vermont. Parts were merged into a new road to form the Windham County Turnpike, an improved toll and stage road, in 1802. A southern section of the old Albany road became known as the Shun Pike from 1802 to 1836 as locals travelled on it to avoid tolls. In 1836, the toll gates were removed and the Windham County Turnpike became a public road, supported by local taxes.

The new road was a primary route for six-horse freight teams that travelled the mountains from Brattleboro to Bennington to Troy, New York, and then to the Erie Canal. It was named a state highway in 1931 and paved shortly thereafter. Postcards from the 1920s and '30s began referring to the highway as "the Molly Stark Trail," reflecting pride in Vermont's roots and traditions. In 1937, the Trail was recognized by the state for its historic and tourism values, but it was not until 1967 that the highway was officially named "The Molly Stark Trail" by the State of Vermont. In 1995, the Molly Stark Trail was designated a Vermont Scenic Byway.

To celebrate the history of the Molly Stark Trail, the Molly Stark Byway Commission has erected a series of 8 obelisks along the route featuring pertinent local history. You can find the location of each of these obelisks on the map.