Nestled between the Taconic and Green Mountains, and enriched by the waters of the famous Batten Kill, The Shires has long been a popular four-season destination for those seeking an authentic Vermont experience. Anchored by the two county seats of Bennington and Manchester, fifteen towns and villages are united by a common sense of place, history, and culture. The Shires of Vermont Byway connects the Southshire with the Northshire and beckons visitors to enjoy scenery, hospitality, recreation, and the region’s rich heritage.

Mohawks and Iroquois traced this path as long ago as 5,000 BC, as evidenced by projectile points, but Vermont was not settled by those of European origin until the 1760s. This Byway, then a crude path marked by occasional slashes on trees, became a principal route of migrating pioneers and their cattle trudging northward from Litchfield and Berkshire counties seeking life in wilderness newly opened to settlement.

Today it offers a quintessential Vermont road trip experience! Visit a farmers’ markets or browse a neighborhood bakery. Pick your own apples and strawberries. Sip craft cocktails at a boutique hotel or pack a picnic to go from one of our mom-and-pop markets. Take in the views, visit galleries, museums, and historic sites. And stop every so often to sample craft brews, hard cider, farmstead cheeses, and fine chocolates — all in a single drive.