Learn about Revolutionary War history, see a silk-covered bridge from 1889, hiking trails, camping, antique shops, museums, and Rudyard Kipling’s residence.

Bennington, VT driving route mapWhat is now Vermont Route Nine was the direction taken by General Stark as he lead his troops across Vermont to defeat the British, August 1777. To confuse the opponents, General Stark referred to the route they were taking as, “The Molly Stark Trail.” Molly was both a doctor and a nurse to her husband’s troops during a smallpox epidemic, using their house as a hospital. You may see some of what Molly Stark may have seen when her husband John fought the Battle of Bennington, but we guarantee that your passage along the Molly Stark Trail will be a lot easier than a trek along this path would have been at the time of the Revolutionary War.

Start in the town of Bennington, the Bennington Battle Monument, the tallest human-built structure in the state or at the Bennington Arts Center, the Old First Church where Robert Frost is buried.  Take the elevator to the observation deck to get your bearings. There’s also the Grandma Moses’s Gallery, with its collection of works by the popular folk artist. As you continue east on Route Nine, watch out for the 1889 silk-covered bridge on Silk Road, spanning the Walloomsac River. Just inside the Green Mountain National Forest, you’ll come to the town of Woodford Hollow with great shops and restaurants–including the Molly Stark Antique store. If you’d rather hike than shop, you’ll find plenty to do at Woodford State Park with its numerous hiking trails, including private and public campgrounds.

Next is the town of Wilmington. Stop at the Mount Snow Valley Chamber of Commerce for a walking tour guide to this memorable historic town. Settled in 1831 and home to the Hoosac Tunnel and Wilmington Railroad, it has plenty of antique stores and specialty shops. Check out Norton House for handmade quilts and other Vermont delights.  Another public campground, in the East of Wilmington is the Molly Stark State Park. Next, Route Nine passes through the town of Marlboro, (named for the Duke of Marlborough), before continuing to West Brattleboro, where you’ll see the 1879 Creamery Covered Bridge. The drive finishes a bit farther east in the town of Brattleboro, where you can shop at the Outlet Center or your choice of antique shops; or you may opt for a visit to the Brattleboro Museum and Art Center. For a more literary side trip, take a left turn onto Black Mountain Road at the junction of U.S. 5 to Kipling Road, where you’ll see Naulahka, Rudyard Kipling’s home for several years. He wrote The Jungle Books and Captains Courageous  here.

Starting Point:
Bennington, VT

Distance of Drive:
46 miles

Check out the waffle weaves! The world's best car drying towel.

Must Eat:
Marina Restaurant
28 Springtree Road, Battleboro, VT 05301
Phone: 802-257-7563
Call ahead to confirm hours of operation.
Good Stop For: Hamburgers and pasta

Best Time of Year for Drive:
Spring to Late fall–great colors in the fall

Points of Interest on Drive:
Brattleboro Museum and Art Center
Grandma Moses’s Gallery
Bennington Arts Center

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Filed under: Best Road Trips