[1] Native Americans inhabited the area that would become Winchester for thousands of years prior to European colonization of the Americas.

At the time of contact, the area was inhabited by the Naumkeag people, from whom the land that would become Winchester was purchased for the settlement of Charlestown in 1639.

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.

It flourished from 1803 to 1836, until the Boston and Lowell Railroad completed a line which neatly bisected the town and provided it with two stations.

Industries small and large followed, including the Beggs and Cobb tannery and the Winn Watch Hand factory which would operate well into the 20th century.

By the time of the Civil War, to which Winchester lent many citizens, the need for a municipal water supply became apparent.

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 20th century, growth continued apace as Winchester evolved from its agri-industrial roots into the bedroom community it is today.

A rich mix of immigrants—the Irish in the northern and eastern neighborhoods, 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 westside farms and live in the "Plains" to the east—complemented Winchester's Yankee forebears.

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.

[16] Winchester was ranked number 86 on the Bloomberg list of America's 100 Richest Places with an average household income of $204,878 in 2016.

Winchester public schools have achieved superior performances on the MCAS exams since their inception, and the district is consistently ranked by editorial reviews such as Boston Magazine as one of the best in Massachusetts.

[18] The Winchester High School sports teams were known as the "Sachems", a term that refers to people who have been appointed to represent a (native) nation in a meeting of a confederacy council.

In addition, the Methodist church, Winchester Recreation Department, and Creative Corner all offer preschool classes.

Nearby Anderson Regional Transportation Center off I-93 (Commerce Way exit) holds a stop for Amtrak's Downeaster train, going through New Hampshire, and terminating in Brunswick, Maine.

134 runs between North Woburn and Wellington Station on the Massachusetts Bay Transportation Authority's (MBTA) Orange Line in Medford.

[27] In 2011 Winchester was selected as one of four communities to participate in the Massachusetts Clean Energy Center (MassCEC) Solarize MASS pilot program.

Most recently, in July 2014, Winchester received a $250,000 Green Communities Grant[29] which helped to offset the cost of installing 1668 cobra-head LED street lights.

Across the Main Street bypass from the high school sits the Jenks Community Center,[30] which offers programs for seniors and other age groups.

Wedge Pond, home to Borggaard Beach and Splash Park, is a popular swimming spot which is continually monitored to ensure safe water quality levels.

And every year, as for over a century, thousands of fans attend the annual Thanksgiving Day football contest between Winchester High School and its long-time traditional rival, Woburn.

In the 1840s, 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.