Bennington retains a coherent pattern of nineteenth-century mill neighborhoods, with owners' mansions and workers' housing in close proximity to their mills. The Holden Mill (BE29) is accompanied by row houses and duplexes for workers that were built on both sides of Benmont Avenue over a forty-year period and by a two-story, brick, Italianate mill store c. 1865 at the corner of Benmont Avenue and River Street.
A series of showpiece owners' houses on Pleasant Street back up to their pottery works along the Walloomsac River, including the Greek Revival Norton houses (BE35, BE36) and the Stick Style/Tudor Revival C. W. Thatcher house 1890 at number 212. At 324 Pleasant Street is the highly decorated wood-frame house of Olin Scott 1887, built adjacent to his 1865 Bennington Machine Works and notable for its elaborate Italianate/Stick Style vocabulary of brackets with pendants, gable screen, and conically capped veranda.
Just east of Bradford Street, the Bradford knitting mill complex, established in 1854 and powered by Barney Brook, is a complete mill neighborhood. On the south side of Main Street is a two-story mill building reconstructed after an 1874 fire composed of three shallow-pitched, gable-roofed sections, with twelve-over-twelve segmental-arched windows and a bell cupola at its east end. South of the mill, at 7–13 Bradford Place, the long gable-roofed brick structure with two double entrances and six-over-six segmental-arched windows was built in 1854 as workers' apartments. Just to the east at 804 Main Street is mill founder Henry Bradford's c. 1860, two-story, clapboard Italianate house with a shallow hipped and balustraded roof, bracketed eaves, belvedere, and carriage house. In 1887 Bradford's son Edward built the large Queen Anne house at 806 Main Street.
Concerned about fire, Bennington's mill owners supported the establishment of a village fire department in 1850 and financed the construction of strategically located firehouses. The first, the Stark Hose Company, was built on Pleasant Street and the second Bradford Hook and Ladder on the site of the Bradford Works. In 1893 mill owner Eli J. Tiffany donated funds to build a replacement nearby at 212 Safford Street. Acquired by the village in 1911, the two-story brick W. H. Bradford Hook and Ladder Firehouse has segmental-arched equipment bays, Eastlake doors, round-headed upper windows, and a corbeled cornice. Shorn of its wooden hose-drying tower and converted into an art gallery, it survives as Bennington's oldest fire-house, a reminder of a necessary component of a mill neighborhood.
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