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The land on which Winchester now sits was purchased from Native Americans by representatives of the setlement of Charlestown in 1639, and the area was first settled in 1640. In the early years of the settlement, the area was known informally as Waterfield, a reference to its many ponds and to the river which bisected the central village. In its second century the area was referred to as Black Horse Village, after the busy tavern and hostelry in its center. Until the middle of the nineteenth century, present day Winchester comprised parts of Medford, Cambridge, and Woburn. The movement toward incorporation of what by this time was called South Woburn was likely precipitated by the rise of the Whig Party in Massachusetts.** The Whigs sought to split a new jurisdiction away from heavily Democratic Woburn, and found enough supporters in the burgeoning village to organize a movement toward incorporation. Representatives of the planned new town selected the name Winchester in recognition of Colonel William P. Winchester of nearby Watertown, who pledged three thousand dollars toward the construction of the first town hall. Upon the signature of then Governor Briggs, the town of Winchester was officially incorporated on April 30, 1850. Curiously, Colonel Winchester did not live to visit the town which had honored his family name. He succumbed to typhoid fever within months of its incorporation.
The town's early growth paralleled improvements in transportation. Prior to incorporation, the Middlesex Canal, linking the Merrimack River to Boston, was completed through then Waterfield. It flourished from 1893-36, until the Boston and Lowell Railroad completed a line which neatly bisected the town and provided it with two stations. Able to deliver passengers as well as goods, the railroad soon bankrupted the canal and spurred more people to move to the area. The first church was built in 1840, the Post Office followed in 1841, and soon after incorporation town schools were started. Industries small and large followed, including the Beggs and Cobb tannery and the Winn Watch Hand factory which would operate well into the twentieth century .
By the time of the Civil War, to which Winchester leant many citizens, the need for a municipal water supply became apparent. Engineers convinced a skeptical public to fund a dam in the highlands to the east of town. The structure blocked the creek which flowed from the Middlesex Fells and produced the first of three reservoirs which continue to provide clear water today.
In the early twentieth century, growth continued apace as Winchester evolved from its agri-industrial roots into the lovely bedroom community it remains. A rich mix of immigrants ... first the Irish in the northern and eastern neighborhoods, then a smattering of African-Americans who flocked to the New Hope Baptist Church in the highlands, and finally Italians who came to work in the west-side farms and live in the "Plains" to the east ... complemented Winchester's Yankee forbears. The constant in these times of change and up to the present has been the public spirited efforts of all to continue to maintain the innate physical charm of the town.
Just as its town government of Selectmen and Town Meeting members has remained essentially unchanged for most of its existence, so has Winchester's flavor little departed from the place that a 1970s survey* listed as "one of top fifteen suburbs" in the nation. Since completion of the "new" Winchester High School in 1972, with population growth finally leveling off, town leaders have had more time and funds to devote to maintaining than molding Winchester's character. Opposite the Main Street bypass from the high school sits the successful Jenks Seniors Center. Across Wedge Pond, town-developed housing for seniors continues to flourish. The Kiwanis club hosts its annual fishing derby on the adjacent shores, while the Rotary Club runs its busy auction nearby. The EnKa Society, a remnant of a long since defunct high school society, continues to raise money for the Winchester Hospital through its annual street fair. And every year, as for over a century, thousands of sports fans attend the annual Thanksgiving Day football contest between Winchester High School and its friendly rival, "parent" town Woburn.
According to the United States Census Bureau, the CDP has a total area of 16.3 km˛ (6.3 mi˛). 15.6 km˛ (6.0 mi˛) of it is land and 0.6 km˛ (0.2 mi˛) of it is water. The total area is 3.97% water.
The town is formed in the shape of a trapezoid whose long axis runs from southwest to northeast. It is roughly bisected by a central valley which is the remnant of the original course of the Merrimack River. After glacial debris effectively rerouted the Merrimack north to its current location, all that remained of its original course through present day Winchester is the quaint Aberjona River and the several ponds it feeds en route to the Mystic Lakes on Winchester's southern border.
On its eastern third, the valley rises steeply into the wooded hills of the Middlesex Fells Reservation, in which lie the North, Middle, and South Reservoirs. The western edge of the valley yields to Arlington and Lexington heights, and the boundaries with those two towns. To the north, the town's longest border is shared with Woburn.