The Molly Stark Scenic Byway follows the path carved out in 1777 when, after the Battle of Bennington, General John Stark and his army returned to New Hampshire via the nearest passage, essentially the same track as today’s Vermont Route 9.

Anchored at each end by two of Vermont’s bustling business and cultural centers - Brattleboro and Bennington – today’s 48-mile Route 9 corridor affords views of rich farmlands west of Bennington through the Green Mountains to the famous three-state-overlook at Hogback Mountain just east of Wilmington to covered bridges leading into Brattleboro and to the Connecticut River.

Ringing with names like Stark, Ethan Allen, Robert Frost and Grandma Moses, the byway wends past famous monuments, unique settlements such as Woodford (at 2,215 feet, the highest village in the state), and important historic districts in Brattleboro, Wilmington and Bennington.

The modern popularity of Route 9 dates back to the dawn of the automobile age and 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 between Fort Dummer outside of Brattleboro, Vermont, to Fort Massachusetts, in North Adams, Massachusetts.

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. In 1802, parts were merged into a new road to form the Windham County Turnpike, a toll and stage road. A southern section of the old Albany road became known as the Shun Pike from 1802 to 1836 as locals took it to avoid tolls. In 1836 the tollgates 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 traveled 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 July 2003, the Vermont State Legislature renamed the route as the Molly Stark Scenic Byway, an official Vermont Scenic Byway.