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Address: Bennington, VT

A 40-mile scenic drive between Bennington and Brattleboro.

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Lovely Drive in the Fall

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... read more

Reviewed 17 November 2016
Jan D
Sugar Grove, Illinois
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31 Reviews from our TripAdvisor Community

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Showing 29: English reviews
Sugar Grove, Illinois
Level Contributor
72 reviews
28 attraction reviews
common_n_attraction_reviews_1bd8 25 helpful votes
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.

Thank Jan D
Maple Shade, New Jersey
Level Contributor
23 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
Reviewed 24 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 cheeses and maple products. This year we decided to drive up and across on our... More 

Thank Deb D
Lubbock, Texas
Level Contributor
83 reviews
38 attraction reviews
common_n_attraction_reviews_1bd8 24 helpful votes
Reviewed 16 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!"

Thank erwretired
Level Contributor
856 reviews
508 attraction reviews
common_n_attraction_reviews_1bd8 335 helpful votes
Reviewed 28 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.

1 Thank mouseHerts
Kent, Connecticut
Level Contributor
219 reviews
29 attraction reviews
common_n_attraction_reviews_1bd8 122 helpful votes
Reviewed 5 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 and Bennington. I guess it is so called because it is the way that John... More 

Thank Howland_Owl
Level Contributor
11 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
Reviewed 12 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!

Thank TonyCastignetti
Auburn, California
Level Contributor
57 reviews
17 attraction reviews
common_n_attraction_reviews_1bd8 36 helpful votes
Reviewed 5 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
Clyde, New York
Level Contributor
114 reviews
68 attraction reviews
common_n_attraction_reviews_1bd8 43 helpful votes
Reviewed 20 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.

5 Thank vcedell
Level Contributor
51 reviews
17 attraction reviews
common_n_attraction_reviews_1bd8 17 helpful votes
Reviewed 9 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!

2 Thank Nancy G
Washington DC, District of Columbia
Level Contributor
2,741 reviews
1,446 attraction reviews
common_n_attraction_reviews_1bd8 1,502 helpful votes
Reviewed 21 June 2015

We drove from Wilmington to Bennington through this road and saw many trees and nice hilltops. I enjoyed the scenery while my husband was driving. I recommend this leisurely drive for those who like to travel slow.

Thank HelenaGuerra

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