Old Bennington Walking Tour

Old Bennington


Bennington, Ralph Earl, 1798, Bennington Museum Collection.

Old Bennington is the earliest permanent settlement in Vermont. It was in June of 1761 that Captain Samuel Robinson led a group of 22 settlers from Massachusetts to the wilderness of Vermont to form a Congregational community centered around a village green and a meeting house. The community grew rapidly, hosting many fine homes, schools, a cemetery, post office and court house. It was a self-sufficient community with many local artisans and merchants to provide services.

The Green Mountain Boys ventured out from here to fight for their land and freedom in the Battle of Bennington. In July of 1777, the proposed Vermont Constitution, prohibiting slavery and offering near universal suffrage, was discussed at the meeting house. Old Bennington produced seven Vermont governors.

As industry grew, activity began to shift downhill along with the Walloomsac River which provided power to operate mills and machinery. Government offices and businesses soon followed, leaving Old Bennington behind as a quiet residential community.

Old Bennington reflects a history of change; homes have been taken down, moved, and renovated but the original character of individualism and freedom remains and continues in the spirit of Bennington and of Vermont

Old Bennington Walking Tour Map


(1) Pliney Dewey House 1800.

Built by son of Jedidiah Dewey, first pastor of First Church. Pliney ran a cider mill by the brook behind the home. Federal Style


(2) Hiram Waters House 1820.

Built as a carpenter shop in 1862 and later converted to a home. Greek revival elements with later Queen Anne embellishments such as the star burst on the pediment. Structure to the side may have been the carpenter shop.


(3) Isaiah Hendryx House 1830.

In this brick home the front door and the windows in the gable reflect the Federal style and the gable end facing the street and the pediment reflect the Greek revival showing the changing architectural styles of the period. Hendryx was a tailor, one of the many merchants in Old Bennington who provided goods and services to the community.


(4) Jedidiah Dewey House 1763.

Built by Jedidiah Dewey, a carpenter and the first pastor of the First Church. This is one of the oldest frame buildings in Vermont built on the orginal “Minister’s Lot” of 420 acres of land, stretching down to the Walloomsack River granted to him by the town proprietors when he accepted the position of Minister at the First Church.


(5) Roberts House 1895.

Built in the Colonial Revival style, it replicates the earlier Federal Style of the other buildings on the street. It was the home of Novelist John Gardner while he taught at Bennington College .


(6) Monument to William Lloyd Garrison

William Lloyd Garrison, the great abolitionist, briefly ran a newspaper, The Journal of the Times in Bennington from 1828 to 1829 before moving on to establish The Liberator.


(7) Colonel Nathaniel Brush Home 1775.

Colonel Bush commanded a Regiment of Vermont Volunteers in Battle of Bennington. Home was renovated in 1824.


(8) Walloomsac Inn 1771.

Orginally the Dewey tavern, It was built by Elijah Dewey, son of Reverend Jedidiah Dewey. During Bennington’s heyday as the jumping-off point for settling the Vermont frontier, the Walloomsack was an important stage stop and one of the village’s commercial and social centers. Prisoners captured in the Battle of Bennington were fed from its kitchens. Presidents Thomas Jefferson and James Madison visited here in 1791 and President Rutherford B. Hayes held a reception celebrating the Centennial of the Battle of Bennington in 1877. Mrs. Theodore Roosevelt and her family and later Walt Disney stayed as well. The inn was in continuous operation as an inn from 1766 to about 1975 and it may be the oldest Inn in Vermont.


(9) Old First Church 1805 and cemetery.

Gathered in 1762, the First Congregational Church is the oldest church in Vermont. The church was dedicated in 1806 to replace the earlier Meeting House located across the street. Designed by noted architect Lavius Fillmore with its Palladian window and open belfry it represents the best of colonial church architecture. It was restored and rededicated as the Shrine of Colonial Vermont in 1937. Robert Frost read his poem ” The Black Cottage” at the ceremony. The cemetery which predates the church is not actually owned by Church, contains graves of many of the founders of Bennington, Governors of Vermont, and a mass grave of German and American soldiers killed in the Battle of Bennington. The earliest grave is of Bridget Harwood who died in 1762. Robert Frost, although not a member of the congregation, is buried here with members of his family.


(10) Bennington Meeting House 1763.

On this site stood the original Meeting House. The building was 40 x 50 feet and served as a school, a church, and Town Hall. After Vermont became a republic the legislature met here. It was taken down and replaced by the First Church in 1805.


(11) The County Courthouse 1847.

This is the third Courthouse to be built in Old Bennington. It burned in 1869 and was rebuilt on South Street in 1872, thus moving the base of power from Old Bennington to what is now downtown Bennington. In Vermont a Shire Town is a county seat and Bennington and Manchester both share that distinction. The June term of the County Court convenes at Bennington and the December term at Mancheaster. Ethan Allen’s home, built in 1769 was just next door. Ethan Allen lived there from 1769 to 1775. An historic monument marks the spot.


(12) Ethan Allen’s House 1769.

Allen built his home on this site and lived here from 1769 to 1775.


(13) Asa Hyde House, Federal Style, 1787.

Asa Hyde, a skilled cabinet maker, came to Bennington from Norwich, Connecticut in 1805 to work with the building of the First Church. He carved many of the details of the church including the columns, pews, and pulpit.


(14) The Catamount Tavern 1767.

The tavern stood on this site and served as the Headquarters of Ethan Allen and the Green Mountain Boys who left from here in 1775 to capture Fort Ticonderoga and later as the headquarters of General Stark who commanded the forces in the Battle of Bennington. British officers captured inthe battle were housed here for a short time. The bronze statue of the Catamount represents a mountain lion snarling at New York which was the sign of the tavern.


(15) Old Academy 1819.

This two story brick building. It was built originally as a school; later it was the Town Library with the fire department in the basement. Note the difference in the brickwork on the front. Just after it was built a windstown blew off the belfrey and part of the facade had to be replaced.


(16) Samuel Robinson’s log cabin 1761.

Robinson’s cabin stood on this site. He was the founder of Bennington and leader of the first settlers who bought  land titles from Governor Benning Wentworth of New Hampshire.


(17) Samuel Raymond House 1821.

This was the residence of the president of the first bank in Bennington, which was located next door. Extensive renovations around 1930 added on a two story addition and sunporch.


(18) General David Robinson House 1795 built in the Georgian style.

General Robinson was the son Samuel Robinson. Note the large Palladian window.


(19) Richard Carpenter HouseOne of the many merchants in Old Bennington, Carpenter operated a tailor shop with Isiah Hendryx. The triple window above the door shows the renovations in the 1890’s.


(20) The Uel Robinson House 1828.

Uel was the grandson of Samuel Robinson. A Greek revival clapboard home. Interestingly, in the Civil War two of Uel’s sons served in the Confederate Army.


(21) Ellenwood-Daniel Conkling House 1810.

This home was enlarged and embellished in the Italianate style in 1859 it sported a cupola at one time. Conkiling’s carriage shop was next door.


(22) Govenor John Robinson House 1860.

This was the home of the first Democratic Governor of Vermont. A vernacular style of both Greek revival and Federal styles.


(23) The Fay-Brown House 1781.

This is the only stone building in Old Bennington and was built as a blacksmith shop until 1857, when it was converted into a dwelling.


(24) Captain David Robinson House 1790.

Robinson was a grandson of Samuel Robinson, one of the founders of Bennington. Upon his death he deeded it to the First Congregational Church for use as a parsonage. For many years the Vermont Gazette was printed in the basement by Anthony Haswell.


(25) The Bennington Battle Monument 1891.

Built to commemorate the Battle of Bennington, the limestone memorial is 306 feet high, making it the tallest structure in Vermont. President Benjamin Harrison attended its dedication in 1891 on the 100th anniversary of Vermont to statehood. Other memorials to Generak Stark, General Warner, and the site of the Continental Storehouse are nearby.


(26) Monument to Seth Warner, leader of the Green Mountain Boys in the Battle of Bennington.

Colonel Warner was the leader of the Green Mountain Boys, a local militia raised to protect Vermont from all outside enemies. Warner was elected leader, replacing Ethan Allen when the Boys joined the Continental Army in 1775.


(27) Monument to John Stark, the hero of Bunker Hill.

John Stark raised 1400 volunteers from New Hampshire and marched them to Bennington.  General Stark was called the victor of the Battle of Bennington. He spoke to the troops before the battle “There they are boys! We beat them today or Molly Stark sleeps a widow tonight!” He points to the battlefield.