9 Sights & Landmarks in Bennington That You Shouldn't Miss

November 8, 2021 Fernanda Pittenger

Bennington is a town in Bennington County, Vermont, in the United States. It is one of two shire towns (county seats) of the county, the other being Manchester. The population is 15,431, as of 2014 US Census estimates. Bennington is the most populous town in southern Vermont, the third-largest town in Vermont (after Essex and Colchester) and the sixth-largest municipality in the state including the cities of Burlington, Rutland, and South Burlington in the count.
Restaurants in Bennington

1. Molly Stark Trail

Bennington, VT http://www.mollystarkbyway.org/
Excellent
67%
Good
30%
Satisfactory
4%
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0%
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Overall Ratings

4.5 based on 57 reviews

Molly Stark Trail

A 40-mile scenic drive between Bennington and Brattleboro.

Reviewed By TrainManDan10 - Keene, United States

My wife and I had a very pleasant ride along Route 9 west of Brattleboro and visited three stops that were well worth our time. First, east of Hogback Mt Scenic Overlook. we stopped at Matt's Maple Syrup outlet where we bought one half gallon of delicious syrup. Second, on the west side of Hogback Mt. Scenic Overlook, we stopped at the Molly Stark State Park where we walked along the trails with our Golden Retriever in quiet woodlands. Thirdly, we stopped at the Hogback Mt Scenic Overlook where one can see for miles and miles.

2. Bennington Battle Monument

15 Monument Cir, Bennington, VT 05201-2134 +1 802-447-0550 [email protected] http://historicsites.vermont.gov/directory/bennington
Excellent
55%
Good
37%
Satisfactory
8%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 720 reviews

Bennington Battle Monument

Monument to a key battle of the American Revolution. The monument stands over 300 feet tall.

Reviewed By amandaeliza23 - Hershey, United States

Loved this stop! If you go up the elevator you get a view of Vermont, New York, and Massachusetts (they have them labeled which I appreciated). The monuments placed around the grassy area were surprisingly interesting too, and continued in a little museum on the ground floor by the elevator. The gift shop was a perfect souvenir treasure trove. Oh, and nice bathrooms are right next to the gift shop too, which is a definite plus mid road trip.

3. Old First Congregational Church

Rt 9 intersection with Monument Avenue, Bennington, VT +1 802-447-1223 http://www.oldfirstchurchbenn.org
Excellent
73%
Good
22%
Satisfactory
5%
Poor
0%
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Overall Ratings

4.5 based on 254 reviews

Old First Congregational Church

This 1805 Bennington church is where poet Robert Frost is buried.

Reviewed By Doc3100 - Traverse City, United States

This is a classic New England church which proudly maintains its Puritan connections. Although an active parish, docents are available during the week to share its history dating back to 1805. From the soapstone foot warmer to the architectural sound dome in the ceiling, you will not want to miss this gem.

4. Bennington Centre Cemetery

1 Monument Cir Old First Congregational Church, Bennington, VT 05201-2134
Excellent
64%
Good
34%
Satisfactory
2%
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0%
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4.5 based on 59 reviews

Bennington Centre Cemetery

Reviewed By S5196IRmichellew

We visited the cemetery on September 14, 2020. There is a veritable whose who of Revolutionary War heroes, early US politicians and State of Vermont founding fathers-and of course Robert Frost's gravesite. The cemetery is well kept. Unobtrusive markers and plaques give visitors a comprehensive history without interfering with the peace of this hallowed ground. Well wroth a stroll. Spend a couple hours wandering through and learning about America's early days.

5. Bennington College

1 College Dr, Bennington, VT 05201-6004
Excellent
53%
Good
37%
Satisfactory
11%
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4.5 based on 19 reviews

Bennington College

6. Silk Road Covered Bridge

Silk Road, Bennington, VT 05201
Excellent
50%
Good
35%
Satisfactory
15%
Poor
1%
Terrible
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Overall Ratings

4.5 based on 185 reviews

Silk Road Covered Bridge

Reviewed By JennyMarie82 - Harrisburg, United States

Disclaimer: no there was not an actual tour it was my own self driving through each of the bridges in Bennington Vermont. What is nice about the three bridges besides the beautiful landscape and preserved structures themselves is that they are conveniently located within five minutes of each other. If you are someone that would like to see covered bridges but do not want to go on a “hunt” for them this trio in Bennington is perfect.

7. Burt Henry Covered Bridge

River Road, Bennington, VT
Excellent
53%
Good
34%
Satisfactory
13%
Poor
0%
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4.5 based on 70 reviews

Burt Henry Covered Bridge

Reviewed By JennyMarie82 - Harrisburg, United States

The Henry bridge is conveniently located near two other active use covered bridges that have been well preserved. As a Pennsylvanian who has explored several areas of covered bridges in my own state most of ours are in active and have been placed in the vicinity of where they were once in use. It is a treat to be able to visit a place that has these beautiful architectural creations and the settings where they are at live up to expectations of being picturesque. There is a place to pull your car over in order to take pictures, etc. I would still caution to watch for vehicles coming through. I am grateful to the state of Vermont for maintaining these historical structures so that many generations can experience them.

8. Papermill Village Bridge

North Bennington, Bennington, VT 05257
Excellent
58%
Good
33%
Satisfactory
8%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 24 reviews

Papermill Village Bridge

Reviewed By N1772UZlaurenb

bring a camera because it is well worthy of picture taking because it has wonderful views with a river underneath , This bridge is in downtown bennington and it is really beautiful in the fall and and winter time as well . Definitely worth visiting !

9. Park–McCullough Historic House

1 Park St, Bennington, VT 05257-9212 +1 802-442-5441 [email protected] http://www.parkmccullough.org/
Excellent
56%
Good
23%
Satisfactory
13%
Poor
5%
Terrible
3%
Overall Ratings

4.0 based on 62 reviews

Park–McCullough Historic House

The Park-McCullough House is the crown jewel of North Bennington, Vermont. Representing 150 years of Vermont history Park-McCullough also serves as a contemporary prism through which citizens of North Bennington and surrounding towns gather to share myriad perspectives and pleasures. The grounds are open daily, and tours are available on weekends. Additionally public programming, theatre and a music series are provided seasonally. Arguably the finest intact Victorian mansion in New England, the house was built in 1864-65 by attorney and entrepreneur Trenor W. Park (1823-1882) who amassed his fortune overseeing the California mining interests of John C. Fremont. Four generations of the family have lived on the property, including two governors, Hiland Hall and John G. McCullough. The thirty-five room mansion stands an important example of American Second Empire Style set on 200 acres in Southern Vermont. The mansion is the perfect venue for unique and memorable weddings and celebrations. Guests may tour the mansion, stroll the grounds, play games on the expansive lawns or relax on the wrap-around veranda during cocktail hour. The Carriage Barn is the perfect venue for live music, receptions and dance.

Reviewed By A7982FImaryf

It was a rainy day on our stay and we were looking for something to do. If you love old house/mansions this place is for you. I loved the fact that mostly everything is original, right down to the clothing. The Director was an excellent tour guide and very informative. The place is very well kept.

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