Southern Vermont Day Trip: Bennington

  • Monument-photo credit Leslie Lello
  • Silk Road Bridge
  • Stark 1

As a kid, my family drove up to Southern Vermont’s Deerfield Valley from New York almost every weekend in winter to ski at Mount Snow.

 Without the Bennington Bypass, this trip was much more arduous than it is today. We had to go right through the center of town which slowed us down considerably.  As an adult, these trips down Bennington’s Main Street made me feel like I had a deeper knowledge up Bennington until the first time took the incorrect exit on the bypass.

 I found myself at an intersection I had never seen before, and it took me an hour of driving around on a dark and snowy winter night to realize I did not really know anything about Bennington.

 This, of course, made me curious about what Bennington had to offer and led me to investigate.

 Luckily, exploring the Southern Vermont town of Bennington is an easy way to spend the day, and a great day trip from Wilmington, Dover & the towns of the Deerfield Valley.

 There are tons of things to do in Bennington, but here are a few great spots to get you familiar with the town.


1. Bennington Battle Monument


The woman in the parked car next to me got out of her car, gazed up and said, "I had no idea how big this thing actually was.”


I can confirm that the Bennington Battle Monument is much larger than one would expect in the humble Southern Vermont town of Bennington.

 If you are standing in an open field gazing at the horizon (the Bennington Welcome Center, for example), the Bennington Battle Monument is impossible to miss.

 Scan the horizon for the giant obelisk on a hill, which towers above all the other man-made structures in its vicinity, and you will have found the monument.

 There is a significance to the location of the monument because it is on the spot where the Continental Army stored armaments and battle supplies during the Revolutionary War. The British Army tried to capture these supplies (which they desperately needed) but the Redcoats lost the battle and failed in their mission to acquire the goods.

 According to the monument’s website, this battle is considered the turning point of the Revolutionary War in favor of the Continental Army.

 One of the best things about this attraction is that during the warmer months you can climb the stairs to the top of the monument and enjoy a gorgeous view. Construction of an elevator to the top of the monument will be completed this year in honor of The Bennington Battle Monument's 125th anniversary.


Access to the top of the Bennington Battle Monument opens April 15, but the grounds are open year round.


Also, keep an eye out for special events that will be held throughout the year in honor of the 125th anniversary of the monument’s existence.

 Visit the Bennington Battle Monument Website for more information.



2. Covered Bridges


How could a driving tour about a quaint Southern Vermont town not mention covered bridges?

 Bennington County has not just one covered bridge, but FIVE! And three are located in the town of Bennington.

 Also, the three out of five covered bridges in the town of Bennington (as opposed to Bennington County) are located near each other in a row and are an easy and logical next stop after visiting the Bennington Battle Monument.


The Silk Covered Bridge is the first one you will get to and most modest in my opinion, without a descriptive plaque and minimal space to pull over.

 The next is the Paper Mill Village Bridge, which offers a plaque that describes the conservation efforts and paper manufacturing related to the area.

 Next, the Burt Henry Covered Bridge offers a nice picnic area and a larger parking area with shade trees to enjoy a little more time to relax in quintessential Vermont scenery.


If you care to visit the other two in Arlington, you have to take a short drive north on Rt. 7a.

 When you exit 7a onto East Arlington Road, you will find the Chiselville Bridge, and finally, the West Arlington Bridge is just a little further off of Rt. 313 West.

 Here is a great map to guide you through the covered bridges of Bennington County.



3. Bennington Potters


Southern Vermont is known for its craftsmanship, and Bennington Potters is a perfect example of the carefully hand-crafted quality goods that come out of the area.

 Founded by David Gil, Bennington Potters has survived a flood, fire, and severe economic downturn, and has continued throughout the years to create handcrafted pottery that is well known for its distinctive style and glazing techniques.

 When you first arrive, you will be directed to the pottery studio with a short self-guided walking tour describing the multi-step process of molding and firing the clay, and displaying bowls and dishes that are in the process of being crafted for sale.

 After your tour of the studio, stop in the gift shop to see (and buy) the beautiful pieces of pottery in their final form.



Your Bennington Road Trip, Mapped Out


To have a nice flow for the day (as is true with most day trips), it is important to balance driving with relaxing and enjoying the sites.

 What To Bring: A cooler. Money for some entrance fees and souvenirs.

 Pick up a to-go lunch in Wilmington (try The Village Roost or Jezebel’s) or on Main Street Bennington (try Crazy Russian Girls Neighborhood Bakery) and toss it in your cooler.





Then head over to the Welcome Center to pick up information and get a great view of the landscape. This is where you can get some great pictures of  the Bennington Battle Monument in the distance, where you will be driving next.

 After visiting the Bennington Battlefield Monument, weave through the town of Bennington’s three covered bridges and park at the Burt Henry Covered Bridge (the third covered bridge) and enjoy lunch at the picnic area.


When you have finished eating, continue your tour of covered bridges up to Arlington, or head back into town to visit Bennington Potters.

 You can finish your day at Bennington’s first brewpub, the Madison Brewing Co. Pub and Restaurant, before heading back to Wilmington.


Click on the Google Map Below for Step-by-Step driving directions:,+VT/Bennington+Welcome+Center,+Bennington,+VT/Bennington+Battle+Monument/Silk+Road+Covered+Bridge/Paper+Mill+Village+Bridge/Henry+(Covered)+Bridge,+Bennington,+VT/Chiselville+Covered+Bridge/Arlington+Covered+Bridge/Bennington+Potters/Madison+Brewing+Company+Pub+%26+Restaurant,+Main+Street,+Bennington,+VT/@42.9864339,-73.2030062,11z/data=!3m1!4b1!4m62!4m61!1m5!1m1!1s0x89e0e5df002b7983:0x16ed4559ee3fe977!2m2!1d-72.8714468!2d42.8683889!1m5!1m1!1s0x89e09694e03d1b17:0x9a32fad82aa871ec!2m2!1d-73.2043414!2d42.9038406!1m5!1m1!1s0x89e096f7e15a9b7f:0xf58e0b3c881d621e!2m2!1d-73.2164833!2d42.8891243!1m5!1m1!1s0x89e096de262a1c51:0xa3c174b82cfe45d!2m2!1d-73.2253793!2d42.9094314!1m5!1m1!1s0x89e097210b3bb365:0xedeaf35214ad5fc9!2m2!1d-73.2334913!2d42.9127477!1m5!1m1!1s0x89e0976a94d61f31:0x9fb7f5616793f4f!2m2!1d-73.2546064!2d42.9122642!1m5!1m1!1s0x89e08b78f42e1e91:0x6106ac7f57ffaa8e!2m2!1d-73.1331617!2d43.0722996!1m5!1m1!1s0x89e0891a54fe387d:0xe80a6b670232da76!2m2!1d-73.2203372!2d43.1043469!1m5!1m1!1s0x89e09662b0a08a35:0x4684d6ebfd81fefc!2m2!1d-73.1945052!2d42.8845357!1m5!1m1!1s0x89e096650396ee55:0x3d4bd5c9bbce0b6b!2m2!1d-73.1963117!2d42.8784169!3e0



Leslie Lello is a photographer, documentary director, writer and photojournalist living in the Southern Vermont.
Some of her clients include ZocDoc.comParty EarthPortrait Simple and North Jersey Media Group.
She splits her time between the New York Metropolitan area and Southern Vermont.
For more information:

Photo credits: Leslie Lello


This blog was purchased by the Bi-Town Marketing Committee with funding provided by the Town of Dover & the Town of Wilmington