Windham County in the southeast corner of the state presents perhaps the most New England–like image of Vermont's counties, sharing a border with Massachusetts and, across the Connecticut River, New Hampshire. From the eastern slopes of the Green Mountains, the Deerfield and Green rivers flow into Massachusetts, while the West and Saxtons rivers flow to the Connecticut, all draining the hilly piedmont interior of the county. Of the county's twenty-four towns, Brattleboro on the Connecticut River is the major population center, with nearly 8,000 residents, while, upriver, Bellows Falls has some 3,000. Wilmington on the upper Deerfield River is the next-largest village, with a population of several hundred. Newfane on the West River is the county seat.
In 1742, the Massachusetts Bay Colony built Fort Dummer at what today is Brattleboro. The goal was to guard against Native American raids, but it was only after the French and Indian Wars that many permanent white settlers arrived. In 1775 disputes between New York and New Hampshire land grantees led to the “Westminster Massacre” at the Windham County courthouse, followed quickly by the Revolution. In 1790 the county had the most populous towns in Vermont; Guilford was the largest with more than 2,400 residents. Whetstone Brook powered mills at Brattleboro, and a major drop in the Connecticut made Bellows Falls another important milling center. By 1800, all but the mountain towns had reached full settlement. Farms covered the landscape, growing wheat and making potash. Accordingly, eighteenth-century dwellings are more common in Windham County than elsewhere in the state, although most have disappeared. Those that survive have traditional central-chimney forms, and many are often now an ell or outbuilding. Almost no public buildings from this period have survived intact, save for the landmark Rockingham Meeting House (WH7).
The county reached 26,760 residents in 1810, but then disease, floods, and failed harvests followed for a decade. Though farmers adjusted and some joined the rising wool craze, particularly in the Connecticut River towns, overall populations in the older towns declined at the same time that the upper Deerfield, West, and Williams river valleys reached full settlement. Federal and early Greek Revival houses and the many white-painted churches built in these years reflect the sophistication of older communities under the influence of pattern books and the simpler, sometimes naive, styling of the more isolated upland towns. A number of the earliest hilltop town centers reverted to farms as meetings and commerce moved downhill toward crossroads and mill villages in the valleys. In Newfane, town meetings and the county court in Newfane Center moved down to Fayetteville (now Newfane village) in the West River Valley, where a new courthouse was erected in 1825. Woolen and paper mills joined the other mills and canal commerce at Bellows Falls, while nearby Saxtons River had a woolen mill and sawmills. Brattleboro became a center for printing, with seven printing presses operating in 1840, along with its cotton factories and mills.
Between 1848 and 1851, several railroads connected Brattleboro, Bellows Falls and White River Junction alongside the Connecticut River. As a result, the clothing mills at Brattleboro village expanded, and it soon became the home of the Estey Organ Company, manufacturers of a fixture in American parlors in the second half of the nineteenth century. Three-story brick commercial blocks lined its Main Street, and its high-quality religious and civic architecture marked the village's status as a regional center, with a street railway and more than 6,000 residents by the 1890s. Bellows Falls also benefited from rail access, as new paper mills opened and manufacturers gradually migrated from Saxtons River, tripling the population to 2,200 residents between 1870 and 1880.
In 1880 the West River Railway from Brattleboro reached the interior of the county, but by then populations in all rural areas were declining, dramatically in some places, so few Victorian farmhouses or large barns are found there. A few dairy farmers in each town did erect large New England bank barns as found elsewhere east of the Green Mountains and these were mostly along the Connecticut River. The timber harvest in the mountains reached its peak between 1880 and 1910, aided by the 1891 Hoosac Tunnel and Wilmington Railroad, and so did the town of Wilmington, thriving with furniture and other wood manufactories and attracting more than 400 residents by 1900.
The International Paper Company expanded in Bellows Falls in 1898, producing one hundred tons of newsprint a day. By 1905 the village began to rival Brattleboro, with 4,800 residents and its own street railway. Although the West River Railway was extended in 1905, the agricultural towns continued their decline, losing one thousand farms between 1890 and 1920. Throughout much of Vermont, this was an era that saw the construction of elaborate town halls and memorial libraries, but from Halifax to Dummerston and Londonderry, rural towns remained largely unchanged. If a memorial library was needed or wanted, recycling a house or school might be managed.
After World War I, modern tastes and the radio ended sales of parlor organs, but in Brattleboro the cotton mills continued, downtown maintained its regional commerce, and auto-oriented businesses began locating on U.S. 5 North. In Bellows Falls hydroelectric generation replaced many mills, and in rural areas the number of farms dwindled to twelve hundred by 1950 and to six hundred and seventy in 1960. The Green Mountain National Forest acquired many of the logged-over mountain towns in the 1940s, subsequently leasing land for ski areas at Haystack, Mount Snow, Stratton, Bromley, and other mountains. “Back-to-the-country” tastes, with a skiing option, brought newcomers, so that many towns have been growing in population for the first time in a century.
Brattleboro, with a Main Street that runs uphill from its old river landing, still has one of the most distinct and vibrant downtowns in the state. Bellows Falls retains a compact collection of turn-of-the-twentieth-century commercial blocks crowned by the 1926 town hall clock tower, as well as notable churches and many fine residences on the river terrace above. Although much of the interior of the county has been returning to forest since 1930, traveling through the former hill farms and village centers is like an exploration of the first half of the nineteenth century, whether on the back roads of Guilford and Halifax, the upland towns along VT 100, or in Newfane, the state's best-preserved early-nineteenth-century county shire.
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