Scenery and History Along The Shires Byway

By Richard Smith

Historic Marker for Jacob Merrit Howard, writer of the 13th AmendmentThis easy 35 mile “Shires Byway” tour, from the Massachusetts border north through Bennington & on to Manchester, combines sites of national importance with gorgeous scenery & side trips. (You can also drive south from Manchester.) As you enjoy 14 state historical markers ( ) plus many other monuments and interpretative signs, please respect private property.

Start your odometer in Pownal, where Rte. 7 enters Vermont, drive north towards Bennington enjoying views of historic Pownal. (Side trip: see 1740s era Dutch homes such as the DeVoet House in Pownal Village.) At a little over six miles from the Massachusetts border, go left on Carpenter Road then immediately right onto Monument Avenue.

Drive one and a half miles to Old Bennington’s 1805 Old First Church (Vermont’s Colonial Shrine) which has Vermont’s oldest Protestant congregation. Park here. The plaque lying down in the center island indicates you’re on the spot where 700 British prisoners were brought after the resounding American victory at the Battle of Bennington, August 1777, two months before the Battle of Saratoga (Turning point of the Revolution). This spot is also where Vermont ratified the US constitution in 1791 to become the 14th state, the first after the original 13. The weathered private home on the corner is the former Dewey Tavern where Thomas Jefferson, James Madison, Walt Disney & other notables visited. The McCullough Mausoleum (north end of the fence) is on the site of Ethan Allen’s home from 1769 to 1775. From here, Allen went north on the Shires Byway (7A) to capture Fort Ticonderoga from the British on May 10, 1775 (America’s First Victory). The cemetery entrance map shows the site of Robert Frost’s (first U.S. poet laureate) grave & the mass grave of British (Hessians) & Americans who died at the Battle of Bennington. Drive north on Monument Avenue to the statue for the Catamount Tavern (former headquarters of the Green Mountain Boys who held off NY land claims).

Revolutionary War re-enactors at the Bennington Battle MonumentContinue to the 306-foot Bennington Battle Monument. Complete with elevator, adjacent gift shop and rest rooms, it is the tallest man-made structure in Vermont. From Monument Circle, take Walloomsac Rd. 500 yards to Fairview then half a mile to Silk. Follow Silk through the c1840 covered bridge to Matteson, then take Rice for less than a mile back to route the Shires Byway(7A) & turn left.

Heading north on historic 7A, at just over one mile is Robert Frost’s former Shaftsbury home (now a museum) where he wrote in 1922 “Passing by the Woods on a Snowy Evening” (part of his Pulitzer Prize winning book). Drive two plus miles further north to the Shaftsbury Historic District. At the Baptist church (Shaftsbury Historical Society), the historic marker describes where Vermont’s Jacob Merritt Howard, sole author of the 13th Amendment abolishing slavery & the basis of the film “Lincoln,” was born. Less than a half-mile north on 7A is the home of former Green Mountain Boy/Vermont governor, Jonas Galusha. Further north, just south of the corner of Old Depot Road 7A is the former Samuel Bottum “safe” house. Now a private residence, it was a stop on the Underground Railroad for runaway slaves.

About five miles more on 7A is Arlington. Ethan Allen lived in Arlington and his first wife is buried in the Episcopal Church cemetery. Norman Rockwell lived in Arlington (from 1939 to 1952) when he painted “the Four Freedoms.” As a side trip, take 313 West about four miles to the covered bridge & Rockwell’s former home/studio, the Inn on the Covered Bridge Green. Return along the scenic unpaved River Road. For another side trip from 7A, go east on East Arlington Road to East Arlington & view Revolutionary War era buildings (some, where Tories hid), an antique shop & a chocolate store. Heading north again on 7A, visit the Sugar Shack (Norman Rockwell prints/museum); go three miles to the Ira Allen House B&B where Ira & his brother Ethan lived. Go another 200 yards north, for a 200-yd. side trip on Hill Farm Road to the Ira Allen Cemetery for spectacular views of Mount Equinox (tallest mountain in the Taconics).

Another three miles north on 7A is Hildene ( ), the magnificent 412-acre estate of Robert Todd Lincoln, Abraham Lincoln’s only son to live to adulthood. Tour the mansion, gardens, Pullman car, etc. Abraham Lincoln descendents are buried in Dellwood cemetery next to the Hildene entrance.

The church and historic marker in Manchester VillageAnother half mile north in Manchester Village (with its historic marker) is the Equinox Hotel, established in 1769. In 1775, Ethan Allen passed though here on his way to capturing Fort Ticonderoga. In 1777, the first government meeting of the newly formed independent Republic of Vermont, took place in the original Marsh Tavern. Also in 1777, New Hampshire’s John Stark defied George Washington here & went South on the Shires Byway to the Battle of Bennington. Later, the Equinox hosted Mary Todd Lincoln in 1863 & 1864 and President William Howard Taft in 1912.

Continue on 7A into Manchester Center. At the large roundabout, turn right onto 11/30. The area from the roundabout to Highland Ave. housed factories which, among other products, milled neighboring Dorset’s quarried marble that ended up as Civil War tombstones or as part of famous buildings in NYC, Boston & Washington, DC.

For more information, please visit the Bennington & Manchester Chambers, Manchester’s Northshire Bookstore as well as their websites. Also, see the Shires Byway website:

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

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