If you want one drive that shows off everything good about Southern Vermont, take the Molly Stark Scenic Byway. This 40-mile stretch of Route 9 connects Brattleboro to Bennington, cutting straight through the Green Mountain National Forest with mountain overlooks, covered bridges, and small towns that haven’t changed much in a hundred years. Locals often call it the Molly Stark Trail, named for the wife of Revolutionary War General John Stark, and it’s officially one of Vermont’s designated scenic byways. Whether you’ve got two hours or a full day, build your trip around one of the most scenic drives in Vermont.
Before you hit the road, spend some time exploring the best things to do in Brattleboro. The town sits right at the byway’s eastern end, where the West and Connecticut Rivers meet, and it’s worth more than a quick pass through. Grab coffee downtown, browse the galleries, and get a feel for the arts scene that’s made Brattleboro one of Vermont’s most interesting small towns. It’s the natural starting point for your drive west, and honestly, a great reason to stick around for a day or two on either side of it.
Inn on Putney Road sits just a short walk from downtown Brattleboro, close enough that you can start your morning with a gourmet breakfast on our porch and be on Route 9 within ten minutes. Our six guest rooms fill up fast during fall foliage season, so if you’re planning to drive the byway when the color peaks, book your room early and make our Vermont Bed and Breakfast your home base for the trip. Book your stay today!
Driving the Molly Stark Scenic Byway
The Molly Stark Scenic Byway runs about 40 miles from Brattleboro to Bennington, and you can drive it in an hour and a half. Most visitors take anywhere from three hours to a full afternoon to drive it, depending on how many stops they make. Don’t rush it. This isn’t a highway you drive to get somewhere; the journey itself is the destination.
Heading west out of Brattleboro, the Molly Stark Scenic Byway climbs into the Green Mountain National Forest almost immediately. The first stop worth making is Hogback Mountain, about 20 minutes in. There’s a scenic overlook here with a hundred-mile view on a clear day, stretching across three states. It’s an easy pull-off, no hiking required.
A few miles past Hogback, you’ll reach Molly Stark State Park, tucked right along the byway itself. If you’ve got even 90 minutes to spare, the Mount Olga Trail here is a moderate 1.7-mile loop that climbs to a fire tower with 360-degree views of the Green Mountains, the Berkshires, and Mount Monadnock in New Hampshire on a clear day. One of the best short trails is hiking at Molly Stark State Park.
Continue west on the Molly Stark Scenic Byway to Wilmington, a classic Vermont village with a walkable downtown, a handful of good lunch spots, and easy access to Mount Snow if you want to extend the trip. From there, the byway winds toward Bennington.
Grandma Moses spent much of her life painting the farms and hillsides around this part of Vermont, and if you’ve ever seen her work, the landscape along this final leg will look familiar. Just before Bennington, you’ll also pass the Robert Frost Stone House Museum in nearby Shaftsbury, where Frost lived while writing “Stopping by Woods on a Snowy Evening” and “Nothing Gold Can Stay”. It’s a short detour off the Molly Stark Scenic Byway.
Bennington itself is the end of the Molly Stark Byway. The Bennington Battle Monument commemorates a Revolutionary War battle fought nearby, tying back to the byway’s namesake, and the town has several covered bridges within a few minutes of downtown if you want to keep exploring before heading back.
Fall is when most people drive the Molly Stark Trail, and for good reason. Peak foliage usually hits this part of Vermont in the first two weeks of October, and the combination of mountain views and hardwood forest along Route 9 makes it one of the better foliage drives in the state. That said, don’t sleep on late spring either. The Green Mountain National Forest turns a deep, saturated green by late May, and you’ll have the overlooks mostly to yourself. There are other Vermont scenic drives near Brattleboro, making it an excellent home base for exploring the fall foliage of Southern Vermont.
Stay Along the Byway at our Brattleboro Bed and Breakfast
After a day on the Molly Stark Scenic Byway, treat yourself to a stay at a historic Vermont Bed and Breakfast just outside downtown Brattleboro. We offer six distinctive guest rooms, beautiful gardens with trails connecting the Retreat Trail network, and a gourmet three-course breakfast every morning to fuel a day of driving and hiking.
Fall is our busiest season for a reason. Guests come for the Molly Stark Scenic Byway, the foliage, covered bridges, and farm stands scattered across the region. If you’re planning to hike at Molly Stark State Park as part of your trip, ask about our Take a Hike package. We’ll pack a picnic for your excursion. Make our Brattleboro Bed and Breakfast your base for exploring one of Vermont’s best scenic drives. Reserve your room now!