Windsor is Vermont's largest county in area, with 55,000 residents in twenty-four towns between the Connecticut River and the spine of the Green Mountains. It encompasses the watersheds of the upper Williams, Black, and Ottauquechee, and the lower half of White River, all of which flow to the Connecticut. The White River joins the Connecticut at Hartford, the county's largest town, with 10,711 residents. Springfield, located where the Black River joins the Connecticut, has about 9,300 residents. Windsor has more than 3,500 residents and Woodstock more than 3,000.
Governor Benning Wentworth of New Hampshire began granting towns in what would become the county in 1761, and by 1763 the English had constructed a military road through the area from Fort No. Four in Charlestown, New Hampshire, to their fort at Crown Point, New York. Settlement followed, with most towns inhabited by the time Vermont declared its independence in 1777 at the Old Constitution House (now a state-owned historic site) in Windsor. After the Revolution, the population rose quickly, to more than 15,000 in 1790 and 34,800 in 1810. Farms raising wheat and sheep blanketed the county in all but the mountain towns, and mill villages developed on the Connecticut and other major rivers. Springfield coalesced around a seventy-four-foot drop in the Black River, Windsor at the fall of Mill Brook to the Connecticut River, and Woodstock had the county-shire business and mills on the Ottauquechee River. That the rapid growth was a boon to Windsor's builders is evident in the finely crafted landmarks that still exist in the county today. Asher Benjamin's influence in Windsor is perhaps foremost in regional importance and influence, but the Georgian buildings that remain in Norwich and Springfield and Federal houses in Royalton and Woodstock are also significant.
When U.S. consul to Lisbon William Jarvis brought Spanish Merino sheep to his farm in Weathersfield in 1811, he started the Merino sheep-raising craze that dominated much of Windsor and Vermont farming through the 1840s. The county became the state leader in agriculture during this period, in part by virtue of its size. All towns reached full settlement as the population topped 40,000 residents, and the pattern of small villages and town centers in the stream and river valleys, which still characterizes the landscape, became firmly established. Industry expanded as woolen mills and other manufactories joined saw-and gristmills at the better waterpower sites in most towns. Ludlow village had two large woolen mills and more than one hundred dwellings; Woodstock had two woolen mills; and Springfield had three cotton and clothing factories. Successful farms and growing villages created demand for many new buildings. Although most followed traditional forms, many distinctive regional characteristics appeared, including the Federal five-bay facade, panel-arch brick masonry, snecked-ashlar stone construction, and the Connecticut River Valley balcony porch. This period also saw the emergence of local variations of Greek Revival.
The Vermont Central Railroad in 1848 and the Connecticut and Passumpsic Rivers Railroad in 1850 joined in Hartford to create the village of White River Junction. Bethel and South Royalton became commercial centers on the Vermont Central, while Windsor benefited from the Connecticut line. In 1849 the Rutland and Burlington Railroad laid track through Chester and Ludlow, and in 1872, the Woodstock Railway connected the county shire with White River. Most of these villages added multistory brick commercial blocks, churches, and houses as local commerce and some manufacturing increased. Villages without a rail connection—such as Grafton, South Woodstock, Weston, and Reading—remained much as they were, and have changed little since. The county had 4,400 farms following the Civil War, but this figure had dropped to 3,700 by 1890, as hill farms from Barnard to Weston were abandoned. But in the river valleys close to rail connections, many farms did well, as their large bank barns attest. In some parts of the county, showpiece gentlemen's farms, such as that of Frederick Billings in Woodstock (WS29), contributed greatly to local agriculture.
Springfield village became the machine-tool capital of the region when the Jones and Lamson Machine Company moved there from Windsor in 1888, the same year a railroad spur connected it with the Connecticut rail line. Fellows Gear Shaper started operations in 1896, and a year later, a streetcar connected the village with Charlestown, New Hampshire. A downtown with brick commercial blocks and distinct socioeconomic neighborhoods blossomed as the village population rose to 3,200 in 1910.
In the first half of the new century inland rural towns lost farms and population, while the manufacturing villages flourished. Between 1890 and 1950, most mountain towns lost half of their already small populations, and twentieth-century barns are largely absent from the county save along the Connecticut and White rivers. Ludlow was sustained by the railroad and the Gay Brothers woolen mill, and Plymouth Notch gained fame as the birthplace and summer White House of President Calvin Coolidge. Windsor industries prospered, particularly the National Acme Company, which had more than 600 employees in the 1920s. Through new house construction, the town introduced some decidedly urban forms to the Vermont scene. Springfield became a state leader in manufacturing, employing more than 10,000 people during World War II, producing machine tools for armament manufacturers throughout the United States. Government-financed housing developments met the need to shelter an expanding population of workers and their families.
After World War II, the number of county farms continued to decline, from 2,000 in 1950 to 1,200 in 1960 and 500 by the 1990s. Although the big woolen mills in Springfield, Ludlow, and Proctorsville closed, Goodyear and National Acme's successors provided several thousand jobs in Windsor, and in 1960 the machine shops in Springfield still employed nearly 4,000. These manufacturing jobs finally went South and overseas in the late 1960s and 1970s. At the same time, development of the ski industry at Killington and Okemo mountains accelerated and helped increase immigration from more urban states. Woodstock remained a status address thanks in part to its patrons, who eventually established the Marsh-Billings-Rockefeller National Historic Park there. The success of the Quechee Lakes development in Hartford and the expansion of Dartmouth College and its Hitchcock Medical Center across the river in Hanover, New Hampshire, also prompted increases in the local population and their income level. The Vermont Law School, founded in 1972, helps sustains South Royalton village and its town. In the twenty-first century, all of these trends continue and shape what remains Vermont's largest and most diverse county.
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