Downtown Bennington Walking Tour

Downtown Bennington

About the tour

This self -guided walking tour begins at the Downtown Welcome Center on South Street, moves up to Putnam Square and then continues to the Walloomsac River Walk before returning to Putnam Square. Parking is provided at the Welcome Center as well as additional lots designated on the map.

Choice of Walking or Driving. For those who enjoy a walk, the tour takes an hour, covering about half a mile from the Welcome Center to the Walloomsac River Walk. Wear comfortable shoes and layered clothing in case the weather changes. Driving is also an option.

Downtown Bennington offers you a wide choice of shops and places to eat. Take the historic tour and spend a day in downtown.

Jump to map

Step Back in Time to Experience a Downtown that developed in the nineteenth century by:

  • taking advantage of the waterpower the Walloomsac River offered for mills
  • wresting political dominance from its early rival, Old Bennington, by obtaining the county courthouse
  • linking itself to the outside world through two railroads and eventually a highway system that crossed at Putnam Square

Located along the Walloomsac River, downtown Bennington became the industrial hub of the area. Gristmills to grind grain were among the earliest mills. By 1869, Bennington had 38 stores and businesses, many of them textile mills, including the largest cotton packing sheet factory in the country and others that produced thread and hosiery. Also appearing were saw and lumber mills as well as those that made paper and paper boxes. Foundries to smelt iron, machine shops and at least one tin shop dotted the area. Wagon and cart makers, with blacksmiths to support them, rounded out the industrial complex. Another manufacturer turned out boots, shoes, and trunks.

A community began to develop down the hill from Old Bennington in the early 1800s. By 1850 with a population of 4,000, this downtown community was ten times larger than Old Bennington. The genteel population of Old Bennington made fun of the new village and one sailor referred to the downhill settlement as being as ugly as “Algiers.” In 1847 the Vermont Gazette moved down the hill to the Walloomsac community and the Bennington Post Office followed the newspaper. Old Bennington fought back and was able to have its own post office, but by 1870 the new County Courthouse was erected on South Street, a blow to Old Bennington’s political power.

Downtown Bennington also became a transportation hub for the Rutland and Bennington Railroad and the Lebanon Springs Railroad that converged in 1852 at a depot on the street named for it. Later, downtown’s center focused on the “Four Corners” where Main Street was crossed by North and South Streets. It became know as Putnam Square, for its most prominent landmark, the Putnam Hotel erected in 1871. In the twentieth century, Putnam Square at the intersection of US7 and VT9 became covered with automobiles, which were serviced at Bennington’s numerous full service garages.


Old Bennington Walking Tour Map


(1) Downtown Welcome Center

Dating from the 1830s or 1840s, the Downtown Welcome Center is a field stone structure, a form of construction found in early nineteenth-century mill buildings. The outside doorway has a five-light transom and full-length sidelights beneath a heavy stone lintel. Built as a blacksmith shop when Bennington experienced the Industrial Revolution, this building served as a tinsmith shop and then as a wagon shop until 1912. It had various social uses until it became the present Welcome Center. Inside by the staircase the original stonewall is exposed. The existing fireplace was added in the early twentieth century.


(2) Bennington County Courthouse

Bennington County Courthouse was erected in 1936 in the Colonial Revival Style, compatible with the town’s image as a colonial village. While early courthouses were erected in Old Bennington, its current location signifies the importance of downtown. The triangular entrance portico, supported by four monumental Doric columns, contains a clock framed by swags. An open bell cupola, with a gold leafed dome, sits atop the hipped roof.


(3) Bennington Town Offices

The Bennington Town Office was built as the Root family home in 1840. Henry Root started a tinsmith operation in Bennington prior to his involvement in Vermont finance and politics. Its original massing and detailing are characteristic of Greek Revival houses with extensions on either side of the temple front. Note the front porch supported by Doric Columns. In the 1920s, this building was donated for use as the Town office.


(4) 201 South Street

201 South St. is another Greek Revival frame building with projecting portico supported on four fluted Doric columns. This residence has been converted to a commercial building with modern additions.


(5) 113 South Street

113 South St. is an Italianate Revival, three-story brick commercial block erected as an investment by architect/builder Calvin Park for his cousin Trenor Park in 1865. It is the most outstanding building for architectural features in the Downtown Historic District. Note the decorative window heads and decorations on the second and third floor. Although the first floor exterior has been modernized, the inside still retains original features. From 1906-77 it was the last location of the fashionable Drysdale’s Dry Goods Company that was operated by three generations of the same family. Drysdale’s window displays exposed Bennington to the latest clothing styles.


(6) 109 South Street

109 South St. was built in 1870 as downtown’s first courthouse, indicating that downtown was now a center of county government. This five-bay Italianate building has a monumental second story in which the court assembled. The first floor has been modernized with a brick storefront. Until 1939 the courthouse was topped with a tower containing the town clock.


You are now at the Four Corners, the center of Bennington, the intersection of Vt. 9 and US. 7.

(7) Putnam Hotel

With its sweeping curved corner location, the Putnam Hotel was built and financed by Henry W. Putnam in 1871 as a hotel and commercial building. Note that some storefronts are modern while others retain their original cast iron pillars. The upper floor windows have segmental heads and arches, marble keystones and sills. The hotel was formerly known for its 75 rooms of luxurious accommodations and proudly advertised its use of steam heat and electricity when those services were rare. Hotel services ceased in 1967. The building of this hotel demonstrates the early prominence of Bennington as a commercial, transportation and vacation center.


(8) Vermont Federal Bank

This white marble building flows around one of the corners of Putnam Square. Built in 1930 as the Vermont Federal Bank with neo-classical elements, it has a rich interior of Italian and Tennessee marble with gilded detail. The parapet honors commerce with the inscription, “Commerce has made all winds her messenger, all peoples her servants.” This magnificent building is worth seeing inside and out.


(9) 332 West Main Street

332 West Main St. is a three bay three-story Italianate commercial building. It was built in 1868 as The First Vermont Bank. Although the front steps are not original, the door to the right and the stairway leading up to the second floor are. The semi-circular cast iron arch sills were restored in its 1996 as a Tax Act project. The inside was renovated to appear as it did in the mid 1800s.


(10) 324 West Main Street

By 1920, automobile care and sales was a growing business due to Bennington’s major crossroads. 324 West Main St. is a two-story brick building built in 1920 as the Bennington Garage. It has a front façade of brick sections between large bay windows and has recently been renovated for offices.


Now look up East Main St.


(11) 400 Main Street

On the northeast corner, M.P. McDonough, Architect, designed this contemporary store in 2003 on the site of a three-story brick building.


(12) 400 Main Street

This rounded three-story brick commercial building was built to balance the Putnam Hotel. Enos Adams constructed it in 1886. The first floor has been modernized but the façade on the upper floors is original. It was used as the Bennington Post Office with other commercial businesses until 1913. When the Post Office left for its new home, this building became a bank.

The only freestanding clock in Bennington County, this pedestal timepiece was installed in front of this building in 1929 and continues to be controlled by a master clock inside the bank.


(13) Commercial Building

Next door on Main Street is Bennington’s earliest commercial building, built by Enos Adams in 1845. Although this building is lower in height than its neighbor, the top architecture remains the same.


Walk up North Street.

By mid century picturesque Italianate taste eclipsed the Greek Revival as the nation’s most popular style. North Street contains a mix of mid and late nineteenth century commercial buildings and earlier residences. With the Italianate style you should look for molded decorations like scroll-sawn brackets under the eaves. Some buildings have an original apartment on an upper floor for the owner of the business below.


(14) 126 North Street

126 North St. was moved to this site in 1987, the building having been in a textile mill complex, serving as the Thomson Mill Office until 1985. Built around 1920, inside it was elegantly decorated with wood paneling, which has been retained in the current the current office space.


(15) 136-140 North Street

136-140 North St. is a three story Italianate commercial building, decorated by paneled pillars, topped by elegant Corinthian capitals that extend to the cornice, which is supported by on scroll-sawn brackets.


(16) 164 North Street

164 North St. has the original storefront with a recessed single door flanked by single pane showroom windows. The molded eave is on simple scroll-sawn brackets. The interior includes pressed tin walls and ceilings throughout. This structure and the one next to it form a row of relatively uniform storefronts.


(17) 170 North Street

170 North St. has the original storefront, including a recessed double leaf door with transom light flanked by single pane showroom windows. The second floor apartment has a rectangular oriel window above the entrance. Scroll-sawn brackets with applied decoration support the oriel and the building’s cornice.


(18) 186 North Street

186 North St. The second structure of its kind on the tour, Taylor’s Garage is an Art Deco yellow brick veneer structure with a band of leaded and stained glass windows that identify the firm. It was constructed in 1928.



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(19) and (20) 190 North Street

These two buildings recall the era when Bennington was an iron-manufacturing center. The small office was constructed prior to 1850 by L. Grover to serve the next-door foundry. Erected on the riverbank as a foundry prior to 1846, the red brick factory building has a corbelled cornice. In 1864 Henry W. Putnam purchased both for the manufacture of water wheel governors. Putnam later succeeded in the manufacture of various patented light hardware products.


(21) 169 North Street

Iron ore and ocher beds existed near the Walloomsac River. S.H. Brown built an iron foundry on the riverbank at 169 North St. in 1842. It is a two and one half story stone structure. When Henry W. Putnam purchased the building in 1867, it had already been converted to grind grain. A gristmill into the 1920s, then a garage, it was rehabilitated as offices in 1978. Windows are 12/12 with smooth stone lintels and wooden sills, while the interior has sloping window spaces and hewn wooden lintels. Along with the buildings at 190 North St. this structure recognizes Bennington’s role in the Industrial Revolution.


(22) River Walk

The Wallomsac River Walk is a scenic trail with interpretive signage of the history along the Wallomsac River. It is a separate tour that can be taken as an extension of the downtown tour.


Walk back down North & South Streets towards the Welcome Center.


(23) 125 North Street

This temple front Greek Revival has corner pilasters supporting a molded cornice with gable end returns. Attached is a full front porch with Queen Anne scroll-sawn decoration.


Cross Putnam Square.


(24) 118 South Street

This marble Federal Building was listed on the National Register of Historic Places, December 12, 1976. Built as a Post Office and other commercial uses in 1913, it was among the last works by James Knox Taylor, supervising Architect for the U.S. Treasury. It was a Post Office from 1913-1967, a U.S. Federal building until 1996, and then was transferred to the Town of Bennington in 1997 to become the Police Station.


(25) 210 South Street

210 South St. is the third historic garage on the tour. A Neo-Classical Revival structure, it was built as Marshall’s Garage in 1926 to sell and service the growing number of private motorcars in the region. Its design allowed customers to drive into a second floor entrance from Hillside Street to the service department. Cars for sale were on the street level. It became the CB Sports factory in 1969 after remodeling. It has again been remodeled following the standards of the National Register of Historic Places. The first floor has semi-circular arched windows and a central entrance with reproduction Georgian fluted pillars and is painted in Neo-Classical colors.