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Review Highlights
Brattleboro to Bennington

We hoped to be in time for the leaves, in undertaking the Molly Stark Trail, but were a little... read more

Reviewed November 18, 2018
A Leisurely Drive through Southern VT

Molly Stark Trail has a scenic byway designation and that was easy to see why. We drove it both... read more

Reviewed October 16, 2018
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  • Average4%
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“fire tower”(3 reviews)
“great trip”(2 reviews)
A 40-mile scenic drive between Bennington and Brattleboro.
Bennington, VT
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All reviews fire tower nice scenic drive great trip leisurely drive mile view green mountains southern vermont gift shop revolutionary war brattleboro hogsback scenery lakes foliage lookout fall ride
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1 - 10 of 40 reviews
Reviewed November 18, 2018

We hoped to be in time for the leaves, in undertaking the Molly Stark Trail, but were a little late. The elevation of part of the trial meant that the best of the 'turn' had been. Can't be helped - it varies slightly every year....More

Date of experience: October 2018
Thank Harrison-F-Carter
Reviewed October 16, 2018

Molly Stark Trail has a scenic byway designation and that was easy to see why. We drove it both ways with a few stops along it. It was also foliage season so we were afforded the colors of autumn along the way. We did make...More

Date of experience: October 2018
2  Thank TravelinJoe47
Reviewed September 14, 2018

Molly Stark Trail is a beautiful, scenic road. Lots of neat little stores to stop en route. If you are local it would be a great day trip!

Date of experience: September 2018
1  Thank 757SueH
Reviewed September 12, 2018

The drive to Molly Stark trail is beautiful, as long as you dont have anyone behind you on the road. Definitely do the hike of Mount Olga to the Fire Tower. On the hike you cant see much, but once you get to the Fire...More

Date of experience: September 2018
1  Thank heathermunholland
Reviewed September 3, 2018 via mobile

Very nice drive, moderate traffic and good roads. Expected the road to be narrower, but it was fine. So many places to stop and investigate. History of Molly Stark, wife of revolutionary war General John Stark was interesting. The 100 mile view at Hogback Mountain...More

Date of experience: September 2018
3  Thank bad4bob
Reviewed July 25, 2018 via mobile

We were heading to Portsmouth from Niagara and decided to take the scenic route rather than the interstate. Our GPS was insistent on the interstate and re-routed us without us noticing which required almost an hour of backtracking - but it was worth it!! The...More

Date of experience: July 2018
1  Thank CyTrip
Reviewed April 9, 2018

the time of the year to go on molly stark trail is in the fall . all the colors make it a good place for photos

Date of experience: May 2017
2  Thank kscracedaddy
Reviewed November 1, 2017

I drive on this trail every Tuesday in a Semi truck. I I am going from Wolfeboro, NH to Elmira, NY. I thought it was an interesting and beautiful road with many historical places and towns. I start in Brattleboro, Vt and drive to Bennington,...More

Date of experience: October 2017
7  Thank Gregory C
Reviewed October 31, 2017

An interesting drive through the mountains of Southern Vermont. Unfortunately the foliage was about two weeks behind schedule, the ride was through a series of ponds and lakes, and mountains and straightaway. We did enjoy the outlook which was at a pretty high altitude and...More

Date of experience: September 2017
1  Thank dave2840
Reviewed October 16, 2017

I read this part of the highway was an extraordinary ride through the Green Mountains but....... this early October trip was, to say the least, outstanding. Others extol it at different times but in the prime color time, unsurpassed. We took a loop side road...More

Date of experience: October 2017
Thank johndkohler1
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Questions & Answers
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Summer H
September 17, 2018|
Response from Compass762228 |
.9 miles, steep in places but takes less than an hour to get up to the fire tower.
Travel Forum Posts
Lynette B
Augusta, Georgia
Molly Stark Trail vs. Mohawk Trail (8 Replies)
Hi all, I know this question covers your neighboring state as well, but I'm hoping someone who has driven both of these can steer us in the right direction. Husband and I will be flying into the Hartford, CT airport on October 15th(arriving about 10 am) on our way to see a daughter in college in Troy, NY. We decided to take a little side trip to hopefully see some fall color and are torn between taking the Mohawk Trail from Greenfield west over and up to Bennington and then on to Troy or...More
October 01, 2015|
Response fromJC-NDG|
I don't think you would be disappointed taking the Molly Stark trail (this is route 9, right??). You can stop at the 100 mile view at Hogback mountain where there is also a giftshop. The town of Wilmington is charming and a nice place to stroll around. Brattleboro also has a nice little downtown to stroll around, though it is usually congested with traffic during the day. I am not familiar with the other route, so I can't offer a comparison.
Houston, Texas
Driving from Brattleboro, VT to Newburgh, NY (4 Replies)
Hello! I would like some recommendations for stops and sights to see on one leg of our summer roadtrip: from Brattleboro, VT to Newburgh, NY. We are a family of 4 with 2 young boys, ages 3 and 6. We have a full day to make this drive and will be doing so in the beginning of June. I was thinking of either driving the Molly Stark trail or the Mohawk trail as part of it. Any suggestions on which route to take, and what to stop and see to entertain 2 young boys that won't cost very much money? ...More
May 03, 2017|
Response fromswedishivy2013|
Either road will be beautiful and fairly slow and scenic.
Chicago, Illinois
Bucket list trip to Vermont - advice requested (21 Replies)
We are returning to Vermont after having not been there for 40 years! We have a flight on hold for the last week of September through first week of October. We are pretty eclectic in what we like to do and see, so we are looking forward to getting an all-round feel for the state as it is now. (Our ages/physical health limits hikes to easy/moderate, though.) Would love some advice on our planned itinerary, particularly about staying in Middlebury. - Fly into Albany and drive to Bennington...More
April 16, 2017|
Response fromChris R|
Some of the best views in the state are at the top of the Stowe toll road. Plenty of easy/moderate hiking up there, with near panoramic views. The rec paths in Stowe & Burlington are both superb, with plenty of photo spots. Trattoria Delia and Leunigs are 2 superb restaurants in Burlington. On your way to N. Hero, Niquette Bay state park has some great easy hiking, with a view nice views of the lake. And 2 excellent restaurants are the Blue Paddle Bistro in Grand Isle, and the North Hero...More