Sightseeing in Bennington, VT – Day 1

In 2017, this post returned to the ranks of one of Faith-Filled Family’s Top Posts

sign bennington, vT

Welcome to Bennington, Vermont!

In the third largest town in the state and the largest town in southern Vermont, our family found several places to explore in Bennington, Vermont.

But before we went exploring, I researched this town and found Bennington to be filled with history.

Did you Know? 

  • Bennington was chartered by Colonel Governor Benning Wentworth (the town’s namesake) in 1749, but the town wasn’t settled until after the French and Indian War.
  • This makes Bennington the location of the first town settled in what would later become the state of Vermont.
    This piece of Bennington’s history is implied in the town’s motto which is “It’s Where Vermont begins!”

To experience the history of Bennington, our family decided to first explore a section of town called Old Bennington.
I found a walking tour of Bennington on the internet.  This guide listed the sites to see and the directions to walk, but the walking tour guide I found did not mention the history behind the sites.  Wanting to see the sties in Bennington and know the history behind those sites, I spent some time reaching each stop on the walking tour.

On the day we explored Old Bennington, we had a map, a walking tour guide, and a handful of research notes.  Our family covered a lot of ground that day and on this virtual tour we also have a lot of historical ground to cover.  This walking tour of Bennington spans the time from 1761 to 1963.

A Stepping Stones Guide to Old Bennington

First Stop – The Old Academy

old academy, old bennington, vTThis building was designed to the finest building in the state.  It was constructed in 1821.  The Old Academy served as a private and public school and a public library.  The site of the Old Academy also marks the place where the first settler to Bennington, Captain Samuel Robinson, cleared land and built a cabin.  The year was 1761.

old bennington, vTStop #2.  The Catamount Tavern was built in 1769.  This tavern served as the headquarters for the Green Mountain Boys.

The Green Mountain Boys were a band of volunteers led by Ethan Allen.  Not only did Allen and his Boys fight New York for this area, but they also fought the British for this area during the American Revolutionary War.

In 1871, the Catamount Tavern burned down in 1871.  Not wanting to forget this historic place, a marker was placed at the site of the Catamount Tavern in 1896.


As for the reason a catamount was chosen as a marker for this historic tavern, we learned that:

New Hampshire and New York fought over and claimed this land which would later be known as Vermont.  The “Grantees” from New Hampshire posted a stuffed catamount on the tavern’s sign post to repel the ‘Yorkers’ from New York.  This posting led to the name of this tavern:  The Catamount Tavern.

catamountDid you Know?

A catamount is another name for a cougar, a puma, a mountain lion,
a mountain cat, or a  panther.

This solitary and carnivorous cat once hunted across America as far north as the Yukon and as far south as the Andes.

Reportedly, the catamount covered the largest area of any wild terrestrial mammal in the Western hemisphere.



Stop #3.  The Village Lion Fountain

village lion fountain, bennington, VT

From 1852 to 1922, the National Humane Alliance donated fountains to numerous cities and towns across the US to encourage kind treatment to animals.

In 1906, this organization donated a fountain to Bennington.

These fountains were often constructed from granite and designed with an upper water trough for equines and a lower water trough for canines.

The National Humane Alliance promoted kind treatment to animals, which included proving fresh water for animals.

In 1991, the town of Bennington renovated and converted the fountain into  a drinking water fountain for pedestrians.




Stop #4 The Walloomsac Inn was built in 1764, which reportedly makes it the oldest inn in Vermont.

wallomsac inn, bennington, VT

We learned about this inn from a short video.  I will share a link at the end of this post.

Stop #5 – The “Old First Church” or First Congregational Church

 old first church, bennington, VT         old first church, bennington, VT

The first congregation gathered here in 1762, which makes “Old First Church” the first protestant church in Vermont.  After touring the church, we decided to return on Sunday for worship.

From an internet search and talking with the congregational members, we learned about this historic church.

interior old first church, VTinterior, old first church, VT

For construction, each interior column was hand-planed from a single pine tree trunk.  Each column extends from the basement footers to the ceiling rafters.  (Gary, Belle, and Buddy confirmed this statement when a church member invited them into the basement for a quick tour.)

The funds for construction were primarily provided by the sales of the box pews located on the first floor.  Each contributing family had their own assigned box pew.  Young people and visitors sat in the Free Gallery on the second floor.  (Since this tradition has been discontinued, when we worshipped here our family sat together   in one of the box pews on the ground floor.)

During the worship service, I sat inside a historical church within a box pew and couldn’t keep my mind from wandering.  I imagined Robert Frost standing on the high pulpit and reciting his poem, “The Black Cottage”.
(Frost was not a member of this congregation, but he lived nearby in the town of Shafsbury.  In 1937, Frost had been invited to speak at the rededication ceremony of this church.)

Stop #6 – The Old Burying Ground is the cemetery adjacent to “Old First Church”.  Our family strolled through this quiet place to find the final resting place of one of America’s favorite poets.

fall in VTold first church cemetery, bennington, VT

For our last stop on our first day of Sightseeing in Bennington, Vermont, we walked up Monument Avenue.  With the guide of my research notes, we pointed out the houses designed in the Colonial and Federal architectural styles.

As we walked along this tree-lined avenue, I couldn’t help but notice that on a Road Trip across America we were beginning to accomplish our short term goal of seeing the colors of a New England fall.

dog in VT        autumn in VT

fall leaves on stepping stones, VT

We continued our walk uphill and finally caught a glimpse of our last stop.

battle of bennington monument, VT

When the last stop came into full view,
we stopped and stared.

battle of bennington, VT

The Bennington Monument stands at an impressive height of 306 feet.  Not only is the Bennington Monument reportedly the tallest structure in Vermont, but it is also one of the tallest battle monuments in the world.

In 1889, the final stone of this granite monument was set in 1889 and President President Benjamin Harrison attended the opening ceremonies in 1891.  A reception was held at the Walloomac Inn (remember stop #4?)

Today, the Bennington Monument is open to the public.  We walked around the grounds and went inside the monument.  We learned about the Battle of Bennington from plaques, historical markers, dioramas, and statues.  From these exhibits and being on site, we could imagine this monumental battle.

DSCN4722   DSCN4724   DSCN4723

I enjoyed learning about Brigadier General John Stark.  Prior to our visit to Vermont and this historical walking tour, I had never encountered this important man in any history book.  Stark played an active role in the American Revolutionary War.

dog in green grass
“Thank you for finding me green grass in Vermont!”

After exploring the grounds and the exhibits, we decided to buy tickets to ride an elevator to the top of Bennington Monument.  Since Fannie was not allowed to ride the elevator, we took turns watching her at the base of the monument

Instead of riding the elevator, I wish we could have climbed the 417 steps to the top.  However, the stairway was closed to the public in 1970.







The views from the top of the tallest structure in Vermont were impressive.

inside battle of bennington monument, VT    view from battle of bennington monument, VT

We could see the Green Mountains of Vermont and Mount Greylock in Massachusetts.
They say that we could even see into the state of New York.

view from battle of bennington monument, VT   view from battle of bennington monument, VT

Enjoying the views and the monument, we lingered around the grounds until the monument closed.

battle of bennington monument, VTbattle of bennington monument, VT

If you, like us, aren’t ready to leave this area,
you can watch a video to learn more about the Walloomsac Inn and the Bennington Monument.

This concludes the Stepping Stones Guide to Old Bennington. 

battle of bennington, VT

I hope you enjoyed this virtual tour.
Click here for our 2nd day of Sightseeing in Bennington, VT.

2 thoughts on “Sightseeing in Bennington, VT – Day 1

  1. I went to Bennington College back in the 1970s, and your travelogue brought back many happy memories of the town. Thanks!

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