Old Bennington today is a graceful village of historic homes from the Revolutionary,
Antebellum and Victorian years of our country. The entire village was designated a National
Historic District in 1984. The dominant architectural style is Federal and homes built later, into
the 20th century also favored this style.
Directly across from the village green lies a remarkable cemetery of Revolutionary War heroes
as well as other notable’s including Robert Frost and his immediate family. The Old First Church
was restored in 1937 using the original plans of its master builder and architect, Lavius Fillmore.
The first minister of this Congregational Church was Rev. Jedidiah Dewey and his home still
remains in the village along with the homes of many other early settlers and leaders of this
village. It was the first church in Vermont.
Chartered in 1749 and settled in 1761 we owe a debt of gratitude to Captain Samuel Robinson
who discovered Bennington when he mistook the Hoosac River for the Hudson River upon
returning with his soldiers from exploration of “The Wilderness” known today as Vermont.
Governor Benning Wentworth of New Hampshire had been charged by King George to settle
this territory and Bennington was the first grant given and named after the governor in 1749.
Endowed with natural beauty, located on a wide plateau west of the town of Bennington, Old
Bennington has become a remarkable place to own a home.
When the post office officially made the move in 1848 to the valley, Bennington on The Hill or
Bennington Centre became Old Bennington and Bennington was reorganized. Old Bennington,
over time, took advantage of becoming a residential village as businesses followed the commerce
down the hill. It is quite unique that now, Old Bennington is limited to residential zoning with
some home occupations.
One outstanding example of bygone days is reflected in the
Walloomsac Inn which had originally been the home of Jedidiah Dewey’s son Elijah and still
stands, though closed to the public. A few other grandfathered businesses remained but are no
longer there. The grandest feature of all is The Bennington Battle Monument, commemorating
The Battle of Bennington, a significant turning point in The Revolutionary War.
There are 97 residences mostly on 2+ acres of land with sidewalks shaded by tall trees. We
highly encourage you to get a feel for the village and its history by walking from the Old First
Church and cemetery up Monument Avenue, stopping to read the commemorative plaques
recognizing our heroes in the Revolutionary War and ending at the Bennington Battle
If you cherish history and elegant historic and vintage homes you must put this village on your
list of possibilities.
Hoisington Realty is pleased to provide the following Old Bennington Village Real Estate listings. If you don't find the property you seek here, or if you need more information about Bennington, Please contact us.