Old Bennington Walking Tour

Old Bennington

Bennington, Ralph Earl, 1798, Bennington Museum Collection.

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Chartered in 1749, Bennington was the first town created in Vermont. In June of 1761 twenty-two settlers from Massachusetts came to Old Bennington, in the wilderness of Vermont, under the leadership of Captain Samuel Robinson 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 courthouse. It was a self-contained 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 Council of Safety met in Bennington and wrestled with the affairs of the newly created Republic of Vermont. At the meeting house they discussed the new Vermont constitution, prohibiting slavery and offering near universal male suffrage. Bennington produced six Vermont governors.

However, as industry grew, activity began to shift downhill along the Walloomsac 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 character of individualism and freedom remains and continues in the spirit of Bennington and of Vermont.

OldBenningtonTourMap1) Pliney Dewey House
(2) Hiram Waters House
(3) Isaiah Hendryx House
(4) Jedidiah Dewey House
(5) Roberts House
(6) Monument to William Lloyd Garrison
(7) Colonel Nathaniel Brush Home
(8) Walloomsac Inn
(9) Old First Church
(10) Bennington Meeting House 1763
(11) The County Courthouse 1847
(12) Site of Ethan Allen’s House 1769
(13) Asa Hyde House
(14) The Catamount Tavern 1767
(15) Old Academy
(16) Samuel Robinson’s log cabin
(17) Samuel Raymond House
(18) General David Robinson House
(19) Richard Carpenter House
(20) The Url Robinson House
(21) Ellenwood-Daniel Conkling House
(22) The Fay-Brown House
(23) Governor John Robinson House
(24) Captain David Robinson House
(25) Bennington Battle Monument
(26) Monument to Seth Warner
(27) Monument to John Stark

(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. 
Pliney Dewey House
(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.
Hiram Waters House
(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.
isahia hendryx house
(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.
Jedidiah Dewey House
(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.
Roberts House
(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.
(7) Colonel Nathaniel Brush Home 1775.

Colonel Brush commanded two companies of Vermont militia at the Battle of Bennington. The home was renovated in 1824 and again in the early 1900s.
(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.
(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.
(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 dismantled after the completion of the new church and parts used in other dwellings in the area.
(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.
(12) Site of 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.
(13) Asa Hyde House, 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.
(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.
(15) Old Academy 1819.

This two story brick building having a step 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.
(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.
(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.

(18) General David Robinson House 1795.

General David Robinson was one of the sons of Samuel Robinson. This late Georgian house has elegant columns supporting a frieze above our regional version of the Palladian window.
(19) Richard Carpenter House. 1819.

One of the many tradesmen in Old Bennington, Carpenter operated a tailor shop with Isaiah Hendryx. The triple window above the door shows renovations carried out in the early 1900’s when it was doubled in size, had its roof line changed and the triple windows added above the door.
(20) The Uel Robinson House 1828.

Uel was the grandson of Samuel Robinson. The house is 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.
(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. Ellenwood’s carriage shop was next door.
(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.
(23) Governor 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.
(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.
(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.
(26) Monument to Seth Warner.

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.
(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.
Old Bennington Sites
Walking Tour
The walking tour begins at the Paradise Inn which began as the name of a restaurant that opened in downtown Bennington in 1927 by James Playotis, a Greek self made millionaire who as a teen immigrated to the U.S. from the island of Mitilini. Guests of his restaurant were Muhhammad Ali, Betty Ford, Anthony Hopkins, and Shirly MacLaine. The Paradise Restaurant successfully served guests for nearly 35 years until a fire destroyed the building and surroundings in the downtown area. Plyotis then in 1964 along with his brother-in-law, Peter Pappas, purchased several acres of land behind his home on the west end of Main Street, moved the 1901 house to the back of the property where it still stands today, built a new Paradise Restaurant in its place and added the first of the three existing building that now makes up the Paradise Inn still owned by the same family.
Old Bennington – Turn left onto Main Street (Route 9)
Before any settlers of European Decent appeared, the Bennington area was inhabited by Native Americans who lived and hunted here as ear;y as 5000BC

Mountains surrounded the area protecting the broad, flat valley. Rivers and streams abound and it is rich in wildlife, wood, stone, and minerals. There is also an abundance of rich soil for farming.

Charted in 1749, Bennington was settled in 1761. The area neighboring the Paradise Inn, now known as Old Bennington, was the first part of town to be developed. The Old First Church and the courthouse were two of the first structures in the area. The settlers first sustained activity was farming, but in 1762 small mills appeared using water to power their machinery. During the Industrial Revolution of the  19th century larger factories were built downhill to harness the energy of the abundant water sources. As time went by commerce, housing, and cultural activities clustered in the present downtown area; however, agriculture and manufacturing still remain key aspects of Bennington’s modern economy.
The Bennington Museum
Open 10am to 5pm, Closed Wednesdays. The expansive galleries feature a wide range of exhibits focusing on local arts and industry, including early Vermont furniture, paintings, and glass. The museum also contains the worlds largest collections of both Grandma Moses’s paintings and Bennington Pottery. Look too for the celebrated 1925 luxury car, the Wasp, 16 of which were handcrafted right here in Bennington.
Old First Church Cemetery
The graveyard itself out dates the church building it is adjacent to. Founders of the town of Bennington, Revolutionary Wars soldiers, Vermont governors, and the revered poet Robert Frost were all buried here. Also, Ethan Allen, leader of the famed Green Mountain Boys, once had a home within the cemetery’s grounds.
Old First Church
Open Monday-Saturday 10am-12pm & 1pm-4pm, with services still offered Sunday mornings. First gathered in 1762 this church, now deemed “Vermont’s Colonial Shrine,” still stands as one of the first awe-inspiring examples of early colonial architecture. Much of the early history of Bennington and of Vermont took place within and around this meeting house.
Walloomsac Inn
The Walloomsac Inn was built in 1764, making it the oldest inn in Vermont. Over the years many famous people have stayed at the Walloomsac including Presidents Thomas Jefferson, Ruthford B. Hayes and Benjamin Harrison.
Village Lion Fountain
Originally a watering trough for horses was later converted to a fountain for pedestrian use.
Catamount Tavern
Marked now by a granite & copper statue placed here in 1896, the tavern was built in 1769 and burned down in 1871. It served as headquarters for the Green Mountain Boys while they plotted against the Yorkers and the British; Ethan Allen planned the capture of Fort Ticonderoga and John Stark prepared for his victory in the Battle of Bennington here.
The Old Academy
Built in 1821, the Old Academy was meant to be the finest building in the state. It has had a rich history first as a private school, then as a public one, and finally as Old Bennington’s Public Library.
Bennington Battle Monument
Open 9am-5pm daily. Built in the late 1880s, this monument is a dedication to the famous Battle of Bennington. It was at this location that the American colonists maintained a store of weapons and food which British General Burgoyne needed to sustain his troops. the British were unsuccessful in there attempt to raid the Bennington store and in during the battle lost many men causing them to be defeated at their next two encounters and surrender soon after.