What to do and see in Bennington, Vermont (VT): The Best Budget-friendly Things to do

December 15, 2021 Kaleigh Reichenbach

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. Green Mountain Oasis

469 Main St, Bennington, VT 05201-2159 +1 802-447-2900 [email protected] http://greenmountainoasis.com/
Excellent
86%
Good
11%
Satisfactory
0%
Poor
4%
Terrible
0%
Overall Ratings

5.0 based on 28 reviews

Green Mountain Oasis

A warm and cozy retreat located in the heart of Bennington featuring the areas only couples massage suite. Let our talented therapists relax, refresh and renew your body and spirit.We offer massage, facials, body treatments, manicures/pedicures, mineral makeup and waxing. Also home to Karma Cat Yoga Studio.

2. Oldcastle Theatre Company

331 Main St, Bennington, VT 05201-2112 +1 802-447-0564 [email protected] http://www.oldcastletheatre.org
Excellent
85%
Good
15%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 33 reviews

Oldcastle Theatre Company

We are a professional theatre located in scenic Bennington, VT. Our Main Stage Season runs from June-October. From October through May, we host many events including music, comedy, improv, acting and vocal workshops and many other events. Follow us on Facebook and subscribe to our newsletter at oldcastletheatre.org to stay up with the latest news and special discounts.

Reviewed By Explorist65 - New York City, United States

A small and intimate theater, the Oldcastle Theatre Company draws viewers into the drama and holds them there. We try to travel to Bennington often to see an outstanding performance. Many of their productions deserve a Broadway-sized audience. Kudos to the actors, directors, playwrights, and support staff.

3. Bennington Welcome Center

100 Route 279, Interchange of Routes 279 and 7, Bennington, VT 05201 +1 802-447-2456 [email protected] http://www.bennington.com/?page_id=657
Excellent
90%
Good
7%
Satisfactory
0%
Poor
3%
Terrible
0%
Overall Ratings

5.0 based on 30 reviews

Bennington Welcome Center

Reviewed By lisasN1951ZF - Auburn, United States

We were in town just for the evening, as we were passing through but wanted to stop halfway through. John was very friendly and welcoming and gave us a great list of things to do that fit into the 5 or so hours we had. It was all great! We enjoyed a covered bridge, the monument, we paid our respects to Robert Frost and perused a few shops on Main St. we ended a great little sightseeing tour with dinner at Publyk House and we were not disappointed. Great visit to Bennington!!!

4. Bennington Museum

75 Main St, Bennington, VT 05201-2885 +1 802-447-1571 [email protected] http://www.benningtonmuseum.org/
Excellent
57%
Good
36%
Satisfactory
5%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 366 reviews

Bennington Museum

Bennington Museum - a Museum of Art, History, and Innovation. Home to the largest public collection of Grandma Moses paintings and 19th-century Bennington Pottery, it also presents Battle of Bennington memorabilia and weaponry, and Gilded Age Vermont, highlighting the industrial and cultural innovation of the late 1800s to the 1920s including the 1924 Wasp Touring Car, paintings by William Morris Hunt, and works by Lewis Comfort Tiffany. Bennington Modernism Gallery celebrates the art created from the early 1950s through the mid-1970s by a group of avant-garde artists working in and around Bennington who led the nation in artistic thought and innovation. Artists may include Pat Adams, Paul Feeley, Helen Frankenthaler, Patricia Johanson, Vincent Longo, Kenneth Noland, and Jules Olitski. Early Vermont Life Gallery presents life in Vermont from the time when the earliest European settlers arrived in 1761 to the early 1800s. 14 galleries. Changing exhibitions. Museum Store & more.

Reviewed By Ilanfreedman

This museum has a collection of paintings, furniture, and firearms, even an antique automobile. I liked the Grandma Moses exhibit on display. I also liked the painting of a sleigh.

5. Molly Stark Trail

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

6. 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.

7. 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%
Terrible
0%
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.

8. The Apple Barn and Country Bake Shop

Rt 7 S, Bennington, VT 05201 +1 802-447-7780 http://www.theapplebarn.com/
Excellent
66%
Good
26%
Satisfactory
6%
Poor
0%
Terrible
2%
Overall Ratings

4.5 based on 97 reviews

The Apple Barn and Country Bake Shop

Reviewed By A7982FImaryf

You will want to comeback time after time. The baked goods are just absolutely delicious! The Maple sugar cookies, the apple turnovers, the candy apples, the cheese. Everything is great. Oh and yes it was apple season so I bought a bag of apples (Macoun). I can't say enough about this place. The staff were very helpful and the owner was very nice to talk to. It is no wonder that this place is a success!

9. Hemmings Motor News Filling Station

216 Main St, Bennington, VT 05201-2103 +1 802-447-9652
Excellent
58%
Good
33%
Satisfactory
7%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 55 reviews

Hemmings Motor News Filling Station

Collectible cars on display and memorabilia for car lovers in the gift shop.

Reviewed By billcL5426AB - Woodbridge, United States

Definitely worth swinging by if you're up in Bennington anyhow. Given the Collector Vehicle focus, I'm just astonished that they don't seem to offer the ethanol-free fuel many collectors crave. For that you have to head up Main Street a bit to Stewart's Shops, where they have the 91 octane "good stuff" without the harmful corn husk snot in it.

10. The Bennington Center for the Arts

44 Gypsy Ln, Bennington, VT 05201-9692 +1 802-442-7158 http://www.thebennington.org
Excellent
53%
Good
35%
Satisfactory
7%
Poor
3%
Terrible
2%
Overall Ratings

4.5 based on 60 reviews

The Bennington Center for the Arts

The Bennington Center for the Arts continually exhibits the work of many of the finest representational artists from around the country. In addition to the artwork in the Center's temporary exhibitions, all of which is for sale, The Bennington also has a very impressive permanent collection of Native American art (Navajo rugs, pots, katsinas, paintings of and by Native Americans) as well as bird carvings by Master Carver Floyd Scholz. The Bennington is also home to the Covered Bridge Museum. Visitors of all ages enjoy the exhibits and videos and use the information gathered to better enjoy their travels through these famous structures as they travel through Vermont.

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