Bennington County is named for Bennington Wentworth, who was the governor of the New Hampshire Grants.
Surrounding County Courthouses:
N – Rutland County and Windsor County
E – Windsor County and Windham County
S – Franklin County, Massachusetts and Berkshire County, Massachusetts
W – Rensselaer County, New York and Washington County, New York
Created: March 17, 1778 
County Seat:
Bennington 1778 – present
Manchester 1781 – present
County Courthouse – Bennington ( Southshire )
Location: 207 South Street / Franklin Lane
Built: 1935 – 1936
Style: Classical Revival
Architect: Alfred Olivia St. Jean of Bennington and Henry Leslie Walker of New York
Contractor: Public Works Administration
Description: The building faces east and is a two story building is a red colored brick and concrete structure. The building is located on landscaped grounds in the center of Bennington. The east front has a portico supported by four high white colored columns rising to a pediment at the roof line. On the center of the roof is a small cupola with gold colored dome. The building was a Works Project Administration project.
Note: The courthouse built in 1846 was destroyed by fire in 1869. The previous courthouse was built in 1870 to 1872. The present courthouse s a replica of the 1846 courthouse.
District Courthouse – Bennington ( Southshire )
Location: 160 Veterans Memorial Drive / North Street
Built: 2010 – 2012
Style: Modern
Architect: William Maclay Architects and Ricci Greene Associates
Contractor: DEW Construction Company
Description: The building faces southwest and is a red colored brick and concrete structure. The building is located on spacious landscaped grounds on the north side of the center of Bennington. On the front there is a projecting east section with entrance on the west side and a recessed west section. The roof line is flat. The building is named as the Superior Court and State Office Building.
Old County Courthouse – Bennington ( Southshire )
Location: 109 South Street / Main Street
Built: 1870 – 1870
Style: Italianate
Architect: Hobbs & Sons of Philadelphia, Pennsylvania
Contractor: Henry Putnam
Description: The building faces east and is a two story red colored brick structure. The building forms part of the row of buildings along South Street in the cenyer of Bennington. There is a central entrance with curved canopy above. A large arched window dominates the second story flanked by smaller arched windows. The building served as courthouse until 1937 when the present courthouse was completed and is now the Pennysaver Press.
County Courthouse – Manchester ( Northshire )
Location: Main Street / Union Street
Built: 1822 – 1823
Style: Classical Revival
Architect: Unknown
Contractor: Unknown
Description: The building faces west and is a yellow colored brick structure. The building is located in the center of Manchester. The building has a central entrance on the first story. The roof is gabled with a large square white colored cupola at the front of the building, rising to an octagonal cupola with gold colored dome at the top. The windows have green colored shutters. The building was enlarged in 1849. The Village Office occupies the lower section on the east side.
Note: The courthouse was built by subscription and it is presumed that the Village of Manchester supervised the construction.
History: The county was created in 1778 and Bennington was selected as the county seat. The first courthouse was erected in Bennington. In 1809, the second courthouse was also built in Bennington. The third courthouse was built in 1846 at a cost of $30,000 and was destroyed by fire in 1869. The fourth courthouse was built in 1869 to 12870 and is still standing. The fifth and present courthouse was constructed in 1935 to 1936 at a cost of $97,540. The District Courthouse was constructed in 2010 to 2012. Manchester became the northern county seat in 1781. The court met in meeting houses and taverns of Eliakim Weller and Jared Munson. In 1822 to 1823, the courthouse was built in Manchester.
County Courthouse – Bennington
District Courthouse – Bennington
Old County Courthouse – Bennington
Old County Courthouse – Manchester
Photos taken 2006, 2014 and 2017