Road tripping in Vermont – Windsor and Bennington

Posted on September 22, 2021


So Mr. Ken and I had a fabulous time in the beautiful state of Vermont. We even enjoyed the 3 hour drive up.


On Day 1, we took a road trip to Windsor, Vermont. the “birthplace of Vermont.” This is where the Constitution of Vermont was adopted in 1777.

windsor vt library

Talk about a quintessential small New England town. We stopped in the local library to ask about the self-guided walking tour. The very nice librarian, Barbara, said she had a booklet that she would copy for us to take on our tour.

Nancy in Windsor Vermont

It was so interesting to see the pretty houses. After the self-guided tour, we had lunch at an appropriately (for us) named cafe called Boston Dreams. It turns out the owner was an avid Red Sox fan! We enjoyed a nice conversation with one of the local residents while we ate. Everyone we met was very friendly.


Vermont catamount

On Tuesday of our week in VT we drove to the college town of Bennington and had fun exploring the area. They have some interesting street art including the Catamount (Vermont Mountain Lion) sculptures. This one is called “Cattitude”. They are sponsored by local businesses.

moose in Bennington VT

When it came time for lunch while exploring Bennington, we came across this interesting restaurant. What drew our attention was the life size fiberglass sculpture of a moose. Now anybody who knows anything about food knows that a life size statue of a moose in front of a restaurant means you are in for certain culinary delight, which definitely was the case here! Eating our pizzas next to the moose made them taste especially good!

Bennington Village Chocolate Shoppe
yummy chocolates

Just when we thought things couldn’t get any better than eating pizza next to a life size statue of a moose, we came across this wonderful chocolate shop! It was jam packed with lots of delicious chocolates, all made on site, and gosh, did it smell good inside! We had fun selecting some chocolates and also enjoying some home made gelato while sitting at one of the sidewalk tables.

As you can see, we are eating our way through Vermont. 🙂

Have you ever been to Windsor or Bennington? If so, what did you think?

Image of Windsor Vermont Public Library is courtesy of Windsor VT Library on Wikimedia.