The first permanent settlement in Vermont, Bennington has remained one of its most important and architecturally rich communities. The town includes one of the greatest concentrations of early architecture in the state; outstanding examples of nineteenth-century domestic, industrial, and public buildings; and important manifestations of Colonial Revival and Beaux-Arts. Taken together, these buildings chronicle the community's and the state's evolution from New England frontier to agricultural Eden, manufacturing dynamo, and nostalgic seasonal retreat.
In 1749 Bennington was chartered to speculative proprietors by colonial governor Benning Wentworth of New Hampshire, who gave his name to the first of his New Hampshire Grants. Soon after, Samuel Robinson of Hard-wick, Massachusetts, who became acquainted with the region during the French and Indian Wars, acquired shares with the intent to settle. In 1761 he established Bennington as a haven for Congregationalist Separatists, who assembled large landholdings, developed agriculture (within two decades this would be considered one of the best wheat-producing regions in North America), and established mercantile ties with Albany and Troy, New York. By the time of the Revolution, Bennington had a population of 1,500 people and was surpassed in size and cultural awareness in western New England only by Springfield in Massachusetts. With much to lose as New York pressed counterclaims to their grants with the British crown, Benningtonians engaged in militant political activity. Their town became the hub for the Green Mountain Boys, and ultimately the de facto capital of early Vermont.
Early settlement took place along a prominent ridge above the Walloomsac River crossed by the road from Albany and the main road from Pownal to Shaftsbury. Now known as Old Bennington, this area had a linear green built up with the first meetinghouse in Vermont, taverns, a courthouse, schools, stores, law offices, printers' and mechanics' shops, and substantial houses. The earliest buildings featured eaves fronts, interior chimneys, and hipped or gambrel roofs, and such features as verandas, stoep-like porches, and circular or oval attic lights, suggesting strong ties to late Georgian traditions in the Hudson Valley. The 1790s to the 1820s saw the arrival of Federal tastes, evident in side halls, neoclassical pedimental gables, and elaborate decoration. Period descriptions along with Ralph Earl's 1798 painting Town-scape of Benningtonin the Bennington Museum, which was perhaps the first townscape painted in America, suggest a lively, boomtown quality along a bustling, muddy Main Street. This is difficult to visualize today after more than two centuries of drastic change, including the migration of the village's businesses down the hill to nineteenth-century industrial Bennington, the rerouting of the major north–south stage road (now U.S. 7) to the valley below, the complex elaboration of VT 9 as it angles across remnants of the green, and the loss of perhaps half of the buildings along what is now leafy Monument Avenue. However, what has been preserved as a result of the decline is a remarkable set of early structures, beginning with what is reputedly Vermont's earliest extant frame house, the Jedediah Dewey House (BE28).
Bennington on the hill, the southern shire town of Bennington County astride the stagecoach routes, may have been a viable political, mercantile, and cultural center for the community of 1800. But in the nineteenth century Bennington's productive centers were located at the town's sources of waterpower along Paran Creek and the Walloomsac River at Irish Corner in North Bennington and in East Village. North Bennington and East Village in particular saw population growth in the mid-nineteenth century, followed by commerce and government. The post office opened in East Village in 1847 and the courthouse moved here after a fire destroyed the one on the hill in 1870. It is here that one finds Bennington's vital heritage of commercial, industrial, and Victorian domestic architecture. Mill owners built complexes of mansion, mill, and workers' housing along the Walloomsac River and Barney Brook on Benmont Avenue, Pleasant Street, and E. Main Street. Parallel to the rise of the pottery industry came Greek Revival including the sophisticated designs of lawyer, politician, and historian Hiland Hall (BE36), and with the knitting mills and machine shops came Italianate and then the work of accomplished local Queen Anne/Beaux-Arts architect William C. Bull. Commercial establishments favored Italianate in the business district at the crossroads of VT 7 and 9 (South, North, and Main streets). This was punctuated at the turn of the twentieth century with scattered Beaux-Arts replacements. In North Bennington, industry along Paran Creek and railroad and banking developed by the Park family helped finance stylish structures in Greek, Italianate, Second Empire, and Victorian Gothic vocabularies.
The village on the hill languished until the later decades of the nineteenth century and the construction of the Bennington Battle Monument (BE23). Its siting required the demolition of a score of Main Street buildings then considered shabby and the closure of the northern downhill extension of the main street, increasing the isolation of the neighborhood from the town below. Locally, it reinforced pride in the town's history, stimulated nostalgia for what had been lost, and placed greater value on what remained. Nationally, it promoted the village as a Revolutionary shrine, established Bennington as a tourist site, and drew the attention of wealthy families (especially from Troy, New York) seeking suitable locations for summer residences. In the aftermath of the monument's dedication, Old Bennington was reborn as a gentrified community for wealthy summer people. The new residents bought, restored, and added to old houses, or they built infill structures in Shingle and Colonial Revival styles. They restored the Old Bennington Academy (BE26) and Old First Church (BE27) and they re-landscaped the village, adding a graceful fence to the burial ground. The new residents worked with remarkable sensitivity, creating an environment that can be read both as an important survival of late-eighteenth-and early-nineteenth-century forms and a comprehensive and high-style statement of the Colonial Revival movement.
The influence of newly prominent Old Bennington is evident in the Colonial Revival public buildings that appeared in the lower village and in the metamorphosis of Elm Street from late-nineteenth-century Queen Anne to early-twentieth-century Colonial Revival as it climbed the hill between the two centers. The heirs (McCulloughs and Jennings) of lawyer, railroad magnate, and North Bennington resident Trenor W. Park furthered colonial nostalgia with their acquisition and restoration of old buildings and their patronage of new ones. This culminated in their support for the Colonial Revival buildings at Bennington College (BE17). A half century later, the college became an important architectural patron in its own right, commissioning modern and Postmodern buildings that deliberately move beyond the style of the college's founding generation. Community awareness of Bennington's diverse architectural heritage grew significantly in these years. Catalyzed by the challenges of preserving and utilizing the Park-McCullough House (BE15), of assuring the viability of the commercial village center, and of dealing with the remnants of once-booming industries, the preservation attitudes born in Old Bennington broadened in taste to a pioneering local appreciation for the full range of Vermont's historic building types and styles.
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