Although its charter is a year younger than Rockingham's and neighboring Guilford was larger through the 1790s, for most of its long history Brattleboro has ranked as the most important center in southeastern Vermont. In 1753 Benning Wentworth awarded the town to a company headed by William Brattle of Boston. The cascades of Whetstone Brook just above the Connecticut River were harnessed for grist-and sawmills in 1762 and 1768, and a store and public house opened in 1771 and 1795, establishing the roots of local industry and commerce.
Settlement occurred linearly along principal stage roads to Troy (New York), Hanover (New Hampshire), and Hartford (Connecticut), and then followed topography. Industry clustered around the valley of Whetstone Brook and its adjacent canal, with a tradesmen's district developing along Canal and Clark streets. North of the brook commercial and public buildings occupied a narrow riverine terrace parallel to and above the Connecticut and below a steep hillside to the west. This formed the five-block-long stretch of Main Street before it branched into the northerly Putney Road (U.S. 5) and northwesterly Linden Street (VT 30), around the town green. Residential neighborhoods moved progressively up the hills along the major arteries, then filled in between them.
A bridge (1804) over the Connecticut River into New Hampshire opened turnpike travel to Boston, but the dominant early means of transport and trade was the river itself. In 1805, merchant John Holbrook, who ran flat boats to Hartford, joined his son-in-law in a papermaking and printing business that evolved into the Bible and dictionary printers Holbrook and Fessenden, and established Brattleboro as a printing center. By 1824 more than 2,000 residents populated the prosperous village.
The period 1830 to 1860 brought the railroad (1849) and saw the beginnings of three other mainstays of Brattleboro prosperity—health care, tourism, and organs. The Vermont Lunatic Asylum (WH38) opened its doors in 1836, pioneering a Quaker regimen of structured and humane treatment for mental patients and evolving into one of the largest private psychiatric hospitals in the country. In 1845 Dr. Robert Wesselhoeft opened the first of several hydropathic physical therapy establishments that rapidly drew a wealthy and lettered clientele interested in the salubrious summer climate as much as the treatment. This established the Brattleboro area as a summer destination, attracting such luminaries as Harriet Beecher Stowe, Henry Wadsworth Longfellow, James Russell Lowell, William Dean Howells, and Georgia planter John Stoddard (whose Italianate villa of 1853–1856 by Richard Upjohn has been demolished). In 1852, lead pipe and pump maker Jacob Estey acquired a melodeon shop that he developed into the Estey Organ Company (WH46), the world's largest manufacturer of reed parlor organs.
The success of these commercial ventures is manifest in population growth—from 2,600 in 1840 to 4,400 in 1880 to 7,500 in 1910—and in the evolution of Main Street into a remarkably urban street. It is densely lined at its southern end with multistory commercial blocks from the 1840s through the 1930s and with churches and civic structures to the north. Estey money produced a bank and supported the Baptist church, and wealthy native son George Jones Brooks returned to build a grand Second Empire hotel (WH43), Unitarian church, and town library. The mercantile Carpenter family donated land for a civic fountain. The prosperous community also made a lasting contribution to the arts. The Hunt family, who occupied a grand Federal house at the corner of Main and High streets, produced artist William Morris Hunt and architect Richard Morris Hunt, both of whom practiced briefly in town. The Mead family's elder son, Larkin, began an artistic career by founding a Brattleboro drawing school and crafting an angel in Brattleboro snow before creating such work as a statue of Ethan Allen for the U.S. Capitol, Lincoln's tomb in Springfield, Illinois, and the elaborate local tomb of native son Jubilee Jim Fisk. His younger brother, William Rutherford Mead, became an architect and a partner in McKim, Mead and White.
Late-nineteenth-century prosperity that filled the upper rings of the village with large Queen Anne and Shingle Style houses continued into the twentieth century. Though organ production peaked in the 1890s, the Estey Company remained an industrial force. Adding the production of pipe and ultimately electric organs, it survived until 1958. Street railroads, begun in 1895, connected the village to West Brattleboro, while a collaboration of the Boston and Maine Railroad with the Central Vermont Railway produced a new Union Station in 1915 at 10 Vernon Street. Agricultural and industrial declines in the twentieth century were partially offset by tourism and the appeal of seasonal attractions in southeastern Vermont. People from the urban Northeast, especially after I-91 reached town from the south in 1958, found Brattleboro a convenient gateway to a bucolic hinterland—to see the fall foliage, to ski in southern Vermont, to stay in farmhouses converted into seasonal houses, and to exploit back-to-the land opportunities. In the 1960s and 1970s, a strong counterculture community emerged and Brattleboro became a hub for natural food sources and restaurants. The summer music festival that Blanche Honneger Moyse founded in the 1950s on the campus of tiny Marlboro College, and the 1972 renovation of the former Union Station into the Brattleboro Museum and Art Center have fostered a lively association of the community with the arts. These interests, in turn, led to a significant preservation movement that has helped Brattleboro retain much of the special architectural character that developed over its two centuries of growth.
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