If you look at a map, you will notice a region in the southwest corner of Vermont defined by the Taconic Mountains on the west and the Green Mountains on the east. This area is known as The Shires of Vermont. If the name brings to mind an image of days past or even the magical world of Bilbo Baggins, you aren’t so far wrong. In this small segment of the state, you will find a sampling of everything that makes Vermont so special. Take a step back in time to the days before the Europeans came to settle the New World by experiencing the deep forests and roaring rivers of southwest Vermont. You feel like the only human in this land inhabited by abundant wildlife and soaring birds of prey. As you move along, an opening in the trees might allow a view of a historic village or local farm which doesn’t seem much changed since Ethan Allen was meeting with the Green Mountain Boys. A few miles further and you realize you are still living in the 21st century. Choose from multiple museums, theaters, music venues, and shopping opportunities for a modern dose of arts, culture, and entertainment.
One of the best ways to explore The Shires of Vermont is to follow the three specially designated scenic byways in the region. Start on the Molly Stark Byway which runs east and west along the southern part of the state. Also known as Vermont Route 9, this road connects the city of Brattleboro to that of Bennington, one of the shire towns (historically referred to as a county seat) of the region. Named for the wife of General John Stark who led the Colonial militia to victory at the Battle of Bennington in 1777, the Molly Start Byway offers magnificent views from the top of Hogback Mountain to recreational activities on the Harriman Reservoir in Wilmington. Take in the panoramic view from the top of the Bennington Battle Monument (Don’t worry. There’s an elevator.) or see Grandma Moses’ fascinating artwork at the Bennington Museum.
Next, head north along the Shires of Vermont Byway which begins at Vermont’s southern border in Pownal and follows Route 7 and 7A north to Manchester, the other shire town in the region. Watch for some of the area’s famous covered bridges, historic architecture, and rushing rivers and streams. If hiking or mountain biking is your passion, opportunities abound in and around Manchester. On the other hand, if history is your love, you’ll want to visit Hildene, Robert Todd Lincoln’s summer home in Manchester. Manchester is also home to many fine restaurants and a large number of outlet stores. Go ahead. Indulge yourself.
In Manchester, take Route 30 north for the Stone Valley Byway. The marble and slate quarries in the region not only helped name the valley, but provided the building materials for much of its development. As you wind through the valleys of the Green Mountains along this byway, opportunities for outdoor recreation abound. With multiple state parks from which to choose, hiking, mountain biking, wildlife viewing and other outdoor pursuits are readily available. The towns along the byway offer some of the best historical museums in the area as well as the Hubbardton Battlefield Historic Site, where the Green Mountain Boys made a defiant and successful stand to halt the pursuing British. You will also find the Dorset Theatre, famous for its summer theater. Fall is a special time for a trip along the Stone Valley Byway with magnificent scenery of red, orange, and gold as well as abundant local selections at the many farmers’ markets of the region.
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The Shires of Vermont