Old Bennington Walking Tour

Old Bennington


Bennington, Ralph Earl, 1798, Bennington Museum Collection.

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Old Bennington is the earliest permanent settlement in Vermont. It was in the Spring 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 six Vermont governors.

However, as industry grew, activity began to shift downhill along the Walloomsack River which provided power to operate mills and machinery. Government offices and business 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


Pliney Dewey House Bennington, VT

(1) Pliney Dewey House 1800.

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


Hiram Waters House Bennington, VT

(2) Hiram Waters House 1820.

Waters was a carpenter and built the house at left. The shop, built in 1862, was connected to the home. Both buildings are in the Greek Revival style with later embellishments such as the starburst on the pediment.


Isaiah Hendryx House Bennington, VT

(3) Isaiah Hendryx House 1830.

In this brick house the front door and the gable reflect the Federal style and the gable
facing the street and pediment reflect the Greek revival Style showing the changing architectural styles of the period. Hendryx was a tailor, one of the many tradesmen and merchants that worked in Old Bennington providing goods and services to the community.


Jedidiah Dewey House Bennington, VT

(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. The house is located on the original “Minister’s Lot” of 420 acres that was granted to him by the town proprietors and stretched all the way to the Walloomsac River.


Roberts House Bennington, VT

(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.


Monument to William Lloyd Garrison Bennington, VT

(6) William Lloyd Garrison Marker

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.


Colonel Nathaniel Brush Home Bennington, VT

(7) Colonel Nathaniel Brush Home 1775.

Colonel Bush commanded two companies of Vermont militia at the Battle of Bennington. The home was renovated in 1824.


Walloomsac Inn Bennington, VT

(8) Walloomsac Inn 1771.

Originally 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 Walloomsac Inn was an important stage stop and one of the village’s commercial and social centers. Prisoners captured at the Battle of Bennington were fed from its kitchens, Presidents Thomas Jefferson and James Madison stayed here in 1791, and President Rutherford B. Hayes held a reception at the Inn celebrating the centennial of the Battle of Bennington in 1877. Mrs. Theodore Roosevelt and her family and later Walt Disney were guests as well. The Inn was in continuous operation as an inn into the 1970s and may be the oldest inn in Vermont. It is currently a private residence.


Old First Church Bennington, VT

(9) Old First Church 1805 and cemetery.

The first Protestant congregation in the New Hampshire Grants was gathered on December 3, 1762 at the Meetinghouse. The First Congregational Church, built in 1805, was dedicated in 1806. Designed by noted architect Lavius Fillmore, with its Palladian window and open belfry, it represents the best of
Federal church architecture. It was restored and rededicated as Vermont’s Colonial Shrine in 1937; Robert Frost read a poem at the ceremony. The adjacent cemetery, which predates the church, contains the graves of many of the founders of Bennington, Governors of Vermont, and a mass grave of German and American soldiers killed at the Battle of Bennington. The earliest grave is that of Bridget Harwood who died in 1762. Robert Frost, although not a member of the congregation, is buried here with members of his family.


Bennington Meeting House Bennington, VT

(10) Site of the Bennington Meeting House 1763.

On this site stood the original Meetinghouse. The building was 40 x 50 feet and served as a school, a church, and Town Hall. Prisoners from the Battle of Bennington were held here. The Vermont legislature convened here in 1778. It was taken down after the completion of the Old First Church.


The County Courthouse Bennington, VT

(11) Site of County Courthouse 1847.

This was the third Courthouse to be built in Old Bennington. It burned in 1869 and was rebuilt in a location on South Street, 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 Manchester. Ethan Allen’s home, built in 1769 was next door.


Ethan Allen's House Bennington, VT

(12) Ethan Allen’s House 1769.

Ethan Allen lived here from 1769 to 1775. He is best known as one of the founders of Vermont and for the capture of Fort Ticonderoga early in the Revolutionary War. A historic marker is located a few feet north of the homesite.


Asa Hyde House Bennington, VT

(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 is responsible for many of the features of the church, including the columns, pews, and pulpit.


The Catamount Tavern Bennington, VT

(14) Site of The Catamount Tavern 1767.

Originally the Stephen Fay Tavern, the building 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. General Stark, who commanded the American forces in the Battle of Bennington, conferred here with the leaders of Vermont prior to the Battle. British officers captured in the Battle were housed here for a short time. The bronze statue of the catamount commemorates a stuffed mountain lion that once stood in front of the tavern snarling towards New York, then engaged in land disputes with Vermont.


Old Academy Bennington, VT

(15) Old Academy 1819.

This two story brick building having a steep gable front was originally built as a school; later it served as the town library, with the fire department in the basement. Just after it was built a windstorm blew off the belfry, and part of the facade had to be replaced. Note the difference in the brickwork on the front.


Samuel Robinson's Log Cabin Bennington, VT

(16) Site of Samuel Robinson’s Log Cabin 1761.

Robinson was the founder of Bennington and leader of the first settlers who bought land titles originating from a grant made by Governor Benning Wentworth of New Hampshire in 1749.


Samuel Raymond House Bennington, VT

(17) Samuel Raymond House 1821.

Built of locally made brick, this was the residence of the president of the first bank in Bennington, which was located next door on Bank Street. Extensive renovations around 1930 included a two-story addition and a sunporch.

General David Robinson House Bennington, VT

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

General David Robinson was one of the sons of Samuel Robinson. Built in the Georgian style, the house features a large Palladian window.


Richard Carpenter House Bennington, VT

(19) Richard Carpenter House. 1819.

One of the many tradesmen in Old Bennington, Carpenter operated a tailor shop with Isiah Hendryx. The triple window above the door shows renovations carried out in the 1890s.


The Url Robinson House Bennington, VT

(20) The Uel Robinson House 1828.

Uel was the grandson of Samuel Robinson. A Federal style / Greek Revival clapboard home. Interestingly, two of Uel’s sons moved to South Carolina and served in the Confederate Army during the Civil War.


Ellenwood-Daniel Conkling House Bennington, VT

(21) Ellenwood-Daniel Conkling House 1810.

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


Governor John Robinson House Bennington, VT

(22) The Fay-Brown House 1860.

This is the only stone building in the area and was built as a blacksmith shop. It was converted into a dwelling in 1857 and underwent remodeling in 1937.


The Fay-Brown House Bennington, VT

(23) Govenor John Robinson House 1781.

Robinson, the first Democratic Governor of Vermont, was elected in 1853. The house was built in the vernacular style that combined both Greek Revival and Federal features.


Captain David Robinson House Bennington, VT

(24) Captain David Robinson House 1790.

Robinson was a grandson of Samuel Robinson, one of the founders of Bennington. Upon his death he deeded his house to the First Congregational Church for use as a parsonage.


The Bennington Battle Monument

(25) The Bennington Battle Monument 1891.

Built to commemorate the Battle of Bennington, it is located near the site of the Continental Storehouse which was the object of the British attack. 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 statehood. Memorials to General Stark, Colonel Warner, and printer Anthony Haswell are located nearby.


Monument to Colonel Seth Warner Bennington, VT

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

Seth Warner was a resident of Bennington and successor to Ethan Allen as leader of Green Mountain Boys. Later, when the Green Mountain Boys became a Continental Army regiment, he led them to victory at the Battle of Bennington.


Monument to John Stark Bennington, VT

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

John Stark, one of the heroes of Bunker Hill, raised 1400 volunteers from New Hampshire and was the overall commander at the Battle of Bennington. Rallying his troops before the battle he said “There they are, boys! We beat them today or Molly Stark sleeps a widow tonight!” The sculpture shows General Stark pointing to the battlefield.