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A snowplow clears Monument Avenue in Old Benningon on Sunday after Winter Storm Electra brought heavy snows on Saturday night./Khynna Kuprian
A snowplow clears Monument Avenue in Old Benningon on Sunday after Winter Storm Electra brought heavy snows on Saturday night./Khynna Kuprian
A snowplow clears Monument Avenue in Old Benningon on Sunday after Winter Storm Electra brought heavy snows on Saturday night./Khynna Kuprian

BENNINGTON -- The oldest part of the first town in Vermont, historic Old Bennington is a place of both longtime residents and newcomers.

Currently eight homes are for sale within the small neighborhood, numbering fewer than 90 residences in total.

"There are an exceptionally large number of homes for sale at the moment, but these things tend to fluctuate," said Arnold Ricks, historian and member of the Old Bennington Board of Trustees.

"I can recall once or twice in the past when a similar number of residences were for sale at one time," said Ricks, also a retired professor of modern European history, who has lived in Old Bennington for more than forty years.

Although it has been an area with a varied population of second homeowners for nearly two hundred years, the sense of community is strong among residents, who are both citizens of the Town of Bennington and a separate charter under the state of Vermont, the Village of Old Bennington.

"Bennington is an interesting example of a town that started on a hill and then moved down to where the water was," said Ricks, explaining that in the early 1800s people began moving their families to what is now downtown Bennington.

"It became mostly abandoned," said Ricks of the historic neighborhood which encompasses parts of Monument Ave., West Road, Walloomsac Road, Fairview St., Bank St., upper Elm St. and Catamount Lane.

"There were people living here, but they were mostly old and couldn't afford to keep up their homes," said Ricks. "The people who had money moved downtown."

Crediting the arrival of newcomers from the Troy area with playing a large role in helping to preserve the Village, Ricks considers Old Bennington's history to be unique among some of the earliest-settled towns.

"Seeking to get away from the heat of the city, many people moved over here and found these old houses ready to be taken over," said Ricks. "The fact that these residences still exist is owing to their non-neglect."

Of the eight homes currently for sale, several have storied histories, including the Isaac Tichenor House, home to the third governor of Vermont, and the Brick Academy, also known as the Old Academy Library, located at the corner of Banks St. and Monument Ave.

The current listings within Old Bennington start at $269,000, with the most expensive home prepared to fetch as much as $1.245 million. The Old Bennington Historic District was officially added to the National Register of Historic Places in 1984, and includes the Old First Church, built in 1806.

"Old Bennington today is almost exactly 50 percent and 50 percent, of both full-time residences and seasonal or second homes," said Kathy Hoisington, principal broker and owner of Hoisington Realty.

"There is so much history to the area that really dates back to the Revolutionary Period, which was critical to its evolution," said Hoisington, calling the area "a mecca" for second homes.

"Wealthy people from Troy came in and replicated Victorian or Colonial styles," said Hoisington. "Monument Circle was originally old farms, and all the land around the monument was farmland."

Resident of the historic former Walloomsac Inn, Donna Berry is also the clerk of the Village Board of Trustees, and can remember a time when second-homes were occupied mainly in the summers.

"This area was not so much a pioneer settlement, but a retreat for wealthy people living in New York and Connecticut," said Berry, echoing the historic tale that many in the Village are familiar with.

"They brought real bricks and wood boards with them to build their homes," said Berry, a granddaughter of Walter Berry, who purchased the Inn in the late 1800s, according to the Bennington Museum. The often-photographed but rarely toured property closed to guests in 1990.

"It is a small part of the Town of Bennington, but people still like to come here and enjoy the quiet and the history," said Berry, who estimates that the total length of roads in the neighborhood is just 3.7 miles. 

In contrast, some homes which were once second homes are now primary residences again, according to Bennington Town Clerk Timothy Corcoran.

"As the property values increase, there are fewer people that are available who can afford to live there only part time," said Corcoran, who said he otherwise doesn't see a noticeable change in the makeup of the Village in recent years.

Citizens of the Village of Old Bennington are also fully citizens of the Town of Bennington, and pay taxes to both municipalities.

"I think people in this area of town do feel a responsibility for the historic character that exists here," said Ricks, noting that Village residents benefit from town water and sewer, as well as police and fire department services.

"It's very low-key, but we tend to feel just as much as part of town as anyone else," said Ricks. "We're all a part of the same community."

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