First, Only, Oldest, and Tallest on The Shires of Vermont Byway

by Richard Smith

The only county in Vermont that has two “shire” or court towns is Bennington County hence the byway that runs through it on routes 7 and 7A is called The Shires of Vermont Byway. The first town from Massachusetts is Pownal, which was the first town in Vermont named after a Massachusetts governor. Pownal contains what may be the oldest house continuously occupied house in Vermont, the Mooar / Wright / DeVoet house.

Going north, the first town after Pownal is the shire town of Bennington which was the first town chartered in Vermont by Benning Wentworth of New Hampshire. The first resistance by the Green Mountain Boys to New York claims was in Bennington, which also has the tallest man made structure in Vermont – the Bennington Battle Monument. The ratification of the US constitution making Vermont the 14th state, the first after the original 13, took place in the first meetinghouse in Vermont in Old Bennington. Ethan Allen departed from the Catamount Tavern in Old Bennington and marched north with Green Mountain Boys to capture Fort Ticonderoga for America’s First Victory. Not so pleasant but the first person hung in Vermont, David Redding, was hung in Bennington.

The next town north of Bennington is Shaftsbury, which was the birthplace of Jacob Merrit Howard who was the sole author of the 13th amendment to the US Constitution, which was the first and only amendment passed during the civil war and it banned slavery.

After Shaftsbury is Arlington, which was home to Norman Rockwell from 1939-1952. The first of the
famous Four Freedoms, which were painted in Arlington, was Freedom of Speech. The descendents of the person who the painting was based on, James Edgerton, are also from Arlington. Rockwell’s first studio burned down but his second is still in existence in West Arlington. The first governor of Vermont, Thomas Chittenden, also lived in Arlington. Just north of Arlington is Sunderland with its Ira Allen Inn. It is said that Ethan Allen gave the first copy of his book “Reason: the Only Oracle of Man” to his wife while he lived in the Ira Allen Inn.

The last town on the Shires Byway is the shire town of Manchester where the oldest mail order retailer in the US, Orvis, was founded. The first son of Abraham Lincoln and Mary Todd Lincoln, Robert Todd Lincoln, built his magnificent family home in Manchester, which has 412 acres of spectacular scenery and history. Manchester also was the setting for first wrongful death murder conviction in the US as well as the place the first government, the Council of Safety, of the Republic of Vermont, met. The oldest long-distance hiking trail in the U.S., the Long Trail, goes through Manchester.

Manchester is the last town on the Shires Byway going north. But then again if you are going south on the Shires Byway it is the first.

Richard (Dick) Smith is a best selling author on Vermont history and gives tours for Backroad Discovery Tours

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