Estimated Mileage: 40 miles Estimated Time: 1 hour, 10 mins
The Molly Stark Scenic Byway (Vermont Route 9 from Brattleboro to Bennington) offers riders history, iconic views, and fun, twisty riding when the traffic is right. Ride the Molly Stark early in the morning or midweek to increase your chances of having fun. Plan on stopping at the Hogback Mountain overlook for a three-state view over rolling hills.
The road follows the path General John Stark used to return to New Hampshire after the Battle of Bennington and is a designated a Scenic Byway. The designation signifies that the route has historic significance, beauty and recreational opportunities. There are eight obelisks placed along the road to call out places of historical significance. Look for the markers to brush up on your Vermont history.
The pavement quality is excellent on almost all of the 40 miles between Brattleboro and Bennington. You will find that it is best to ride the road from east to west to due to the strategic location of truck lanes just before twisty sections. The truck lanes allow easy passing of slow moving campers and gawkers who do not understand that smooth flow and ample momentum is needed to enjoy the tasty, twisty 45 mph curves. Riding west to east is also fun, but there are fewer safe passing opportunities.
The overlook at Hogback Mountain in Marlboro is fourteen and half miles west of Brattleboro and is a nice, midway stopping point. The 100-mile view includes the rolling hills of southern Vermont, northern Massachusetts and western New Hampshire. A gift shop here sells Vermont maple syrup, cheese and souvenirs. The Southern Vermont Natural History Museum is located next to the gift shop. The museum has a display of non-releasable live hawks and owls.
From the overlook, the road descends to Wilmington Vermont. Just before reaching Wilmington, a left-hand turn leads to Vermont Route 100 South. One-hundred south of this intersection provides a fun side route that loops back into the Molly Stark west of Wilmington. In Wilmington, VT-100 north intersects with VT-9 at a traffic light with good signage.
You will find everything from creemee stands and pizza to full course dining in Wilmington. You can park your bike on Main Street and walk to your selection. Wilmington also offers shopping and attractions like art galleries. A short hop off the Molly Stark is the Skip Morrow and Art of Humor Gallery (address: #30 Not-A-Road, Wilmington VT – seriously; 10-5 daily; weekdays call (802) 464-5523 ).
West of Wilmington, the road runs along the Deerfield River and climbs up to the intersection with VT-8. There is a truck lane just before the VT-8 turn. The VT-100 south side loop mentioned earlier rejoins the Molly Stark here.
West of VT-8, the road rolls up and down, but generally climbs through wooded areas until Woodford -- Vermont’s highest village at 2,215 feet. From there, the road winds steadily down the 8 miles to Bennington, where it becomes Main Street.
Bennington is the third largest town in Vermont (15,764 2010 census) and has a variety of services. You can find food and lodging all within walking distance of downtown.
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