We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Review Highlights

Found the Molly Stark Trail by complete chance when looking for something to do for a day drive... read more

Reviewed 19 July 2017
Boston, Massachusetts
Lovely Drive in the Fall

Took this route from Bennington VT... About 1-1/2 hours to Brattleboro. Nice scenery and small... read more

Reviewed 17 November 2016
Jan D
Sugar Grove, Illinois
Read all 32 reviews
Sponsored by:
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Sponsored by:
A 40-mile scenic drive between Bennington and Brattleboro.
  • Excellent69%
  • Very good25%
  • Average6%
  • Poor0%
  • Terrible0%
Travellers talk about
“scenic drive” (3 reviews)
“nice ride” (2 reviews)
Bennington, VT
Write a Review
Reviews (32)
Traveller rating
Traveller type
Time of year

1 - 10 of 30 reviews

Reviewed 19 July 2017

Found the Molly Stark Trail by complete chance when looking for something to do for a day drive. Trail has many places to stop and take in the scenery and sights! Hogback Mountain was very pretty!

1  Thank CMC_2012
Reviewed 17 November 2016

Took this route from Bennington VT... About 1-1/2 hours to Brattleboro. Nice scenery and small towns along the way. It was raining that day so we didn't get much of a chance to get outside...still very nice ride.

1  Thank Jan D
Reviewed 23 October 2016

We found this route one year when we were traveling home from New Hampshire. We enjoy driving through for the scenary and fall foliage. There are places to pull over for viewing as well as some covered bridges and antiques and gift shops with vermont...More

Thank Deb D
Reviewed 15 October 2016

Scenic and Historical. Be sure to stop in Wilmington to see statue of Molly Stark - quite interesting. And stop at Hogback Mountain for great views as well as pick up some Vermont Distillery "specials!"

1  Thank erwretired
Reviewed 27 August 2016

This is a very pretty route with mountains and rivers on each side. If you stop at Hogback Mountain, you get incredible views.

4  Thank mouseHerts
Reviewed 4 June 2016

A nice, scenic drive that i used to take to get to Route 100. I still don't understand why they call it the "Molly Stark Trail." Molly didn't do anything but keep the home fires burning while husband John was off fighting at Bunker Hill...More

1  Thank Howland_Owl
Reviewed 11 October 2015

What a nice drive, with beautiful scenery, plenty of places to stop along the way, and a great chance to see so much of southern Vermont, and the great people who live there. Wonderful drive!

1  Thank TonyCastignetti
Reviewed 4 October 2015

This is a very scenic trail during fall foliage. We chose to do it because it was a rainy day and couldn't hike. Beautiful!!

Thank Scuba_Kim_8
Reviewed 19 September 2015 via mobile

My husband and I drove headed towards Bennington. Nice drive. Stopped at the Hogback overlook. Really took our time and enjoyed the stop. Loved the gift shop. Best prices on the maple products that we had seen in the area.

7  Thank vcedell
Reviewed 8 August 2015 via mobile

This was a beautiful and historic routing. Glad we took this road and stopped at the scenic lookout at Hogback Mountain. Whoever is responsible for the overlook needs to replace boards before someone leans on the railing and takes a tumble over the edge!

5  Thank Nancy G
Sponsored by:
Nearby Restaurants
296 reviews
12.30 km away
The Anchor
411 reviews
12.30 km away
Cask & Kiln Kitchen
130 reviews
12.33 km away
147 reviews
13.34 km away
Nearby Attractions
Prospect Mountain Nordic Ski Center
8 reviews
4.79 km away
Mount Snow Resort
403 reviews
13.42 km away
Adams Farm
122 reviews
13.94 km away
Snowmobile Vermont - Mount Snow
51 reviews
13.47 km away
Ask a question
Questions & Answers
7 October 2015|
Response from Howland_Owl |
Gift shop? It is a road.