Vermont Fall Foliage
Driving the Molly Stark Scenic Byway
If you want one drive that captures everything worth seeing in southern Vermont during fall, take the Molly Stark Scenic Byway. This 40-mile stretch of Route 9 connects Brattleboro to Bennington, running straight through the Green Mountain National Forest with mountain overlooks, covered bridges, and small towns that have barely changed in a century. Locals call it the Molly Stark Trail, named for the wife of Revolutionary War General John Stark. Whether you have two hours or a full day, this byway belongs on your Vermont road trip itinerary.
Start in Brattleboro, where the West and Connecticut Rivers meet at the byway’s eastern end. The town has a walkable downtown, working art galleries, and enough coffee shops and bookstores to fill a morning before you ever get on the road. Give yourself time here. Brattleboro is one of Vermont’s most interesting small towns.
What to See Along Route 9 Vermont
Heading west out of Brattleboro, the byway climbs into the Green Mountain National Forest almost immediately. About 20 minutes in, pull off at Hogback Mountain for a scenic overlook with a hundred-mile view across three states on a clear day. No hiking required.
A few miles past Hogback, Molly Stark State Park sits directly along the route. If you have 90 minutes to spare, the Mount Olga Trail is a moderate 1.7-mile loop that climbs to a fire tower with views of the Green Mountains, the Berkshires, and Mount Monadnock in New Hampshire.
From there, the byway continues to Wilmington, a walkable village with good lunch spots and easy access to Mount Snow. The final stretch toward Bennington passes the Robert Frost Stone House Museum in Shaftsbury, where Frost wrote two of his best-known poems, before ending at the Bennington Battle Monument and the town’s covered bridges.
Peak fall foliage along this stretch of Vermont scenic drives usually hits in the first two weeks of October, when the hardwood forest along Route 9 turns deep red and gold against the mountain overlooks. Late spring is worth considering too. By late May, the Green Mountain National Forest is a saturated green, and the overlooks are nearly empty.
Stay at a Brattleboro Bed and Breakfast Before You Drive
The Inn on Putney Road is a six-room French Baronial-style manor, a short walk from downtown Brattleboro, set on an acre of gardens along the West River with direct access to over 17 miles of hiking trails. Start your morning with a two-course gourmet breakfast made from local Vermont ingredients, then be on Route 9 within ten minutes.
Guest rooms fill quickly during foliage season, so if you’re planning to drive the Molly Stark Scenic Byway when the color peaks, book early. As one of the more established options among Vermont scenic byways for a home base, this Brattleboro Bed and Breakfast puts you close to the route and close to town.
Frequently Asked Questions
What is the Molly Stark Scenic Byway?
It is a 40-mile designated Vermont scenic byway running along Route 9 from Brattleboro to Bennington, passing through the Green Mountain National Forest.
How long does it take to drive the Molly Stark Trail?
The drive itself takes about 90 minutes without stops, though most visitors spend three hours to a full afternoon, including overlooks and short hikes.
What is there to see at Hogback Mountain?
Hogback Mountain has a roadside scenic overlook offering views across three states on a clear day, with no hiking required to reach it.
Are there hiking trails at Molly Stark State Park?
Yes. The Mount Olga Trail is a 1.7-mile moderate loop to a fire tower with views of the Green Mountains, the Berkshires, and Mount Monadnock.
Who was Molly Stark?
Molly Stark was the wife of Revolutionary War General John Stark, and the byway takes its name from her.
Book your stay at the Inn on Putney Road today and make our Brattleboro Bed and Breakfast your base for one of Vermont’s best fall foliage drives.