When the first British colonists arrived in New England during the 17th century, the native inhabitants of the area now incorporated into the Town of Winchester were members of the Massachusett tribe. The original colonists were Puritans led by Gov. John Winthrop. The first colonial town to which Winchester territory belonged was Charlestown. It is with these three entities that the history of Winchester began.

Through the early nineteenth century, Winchester’s inhabitants continued to be primarily English, many descendants of the first settlers. As waves of immigrants came to the United States and as the Industrial Revolution transformed the town’s economic structure, Winchester’s population began to change. The Irish and later Italians were the most numerous among the new nationalities, bringing with them the challenge of assimilating a different religion, as well as a variety of ethnic identities. The end of the nineteenth century saw African Americans move from the American South into Winchester. Early in the twentieth century, Russian immigrants introduced a small, transitory Jewish element into the community. By the mid-twentieth century, a wide variety of European nationalities were represented in the population, though they did not form distinct neighborhoods as earlier groups did. Immigrants from Asia Pacific were extremely few until the end of the twentieth century. Early in the twenty-first century, over a hundred nationalities and languages appeared in the public schools.



The native leaders (or sachems) with whom the first colonists of the Massachusetts Bay interacted were the sons and widow of Nanepashemet, the great sachem of the Massachusett tribe, killed by the Tarratine of Maine before the Puritan colonists arrived in New England. The colonists of Charlestown were met by the eldest son, Wonohaquaham, whom they called Sagamore John. But in 1633, a smallpox epidemic claimed not only his life but also that of his brother Montowampate or Sagamore James. Presumably because the third surviving son of Nanepashemet was too young, the English negotiated for the land which includes what is now Winchester (and many other communities) with the great chief’s widow, known only as the Squaw Sachem. (Above: the central portion of a library mural entitled "The Beginning of Winchester" or "Purchase of Land from the Indians.")

The deeds executed with the Squaw Sachem, along with the Charlestown record of the original allotment of the deeded land, have traditionally marked the beginning of the settlement that grew into Winchester. Early Winchester historians described the relationship with the Squaw Sachem as friendly, though relations between the colonists and the native people were actually complex. Within Winchester boundaries, they were also short-lived since, after the native queen died (probably 1650) and particularly after King Philip’s War, Native Americans moved away from the area. [Read more: The Massachusett Tribe, Beginning of Winchester on Massachusett Land and Tales of the Woods.]


Following some early settlements on Cape Ann and at Salem, the Massachusetts Bay Company organized the great Puritan migration from England to New England (1629-1642).

Tercentenary ArabellaThe first fleet brought enough settlers to Salem that the Puritan colonists began to move to others areas. Charlestown was first settled in 1629. The fleet of 1630 included 11 ships which brought about 1,000 settlers to the Massachusetts Bay. In this fleet was the Arbella (depicted left during the Massachusetts Bay Tercentenary), which carried the first governor, John Winthrop, and the company’s charter. Although the Arbella landed at Salem, the people quickly dispersed to Charlestown, Boston, and nearby lands. When Winthrop arrived, Sagamore John gave the colonists permission to build where they liked (according to Charlestown records), which they indeed did, many moving to Boston.

Winthrop himself settled in Charlestown which grew rapidly through the era of the Great Migration to a possible high of 15,000 colonists within 21 communities in 1642. In 1633, the General Court, which had the duty to set town bounds, granted to Charlestown some additional territory to the north, defined in 1636 as extending eight miles into the country. In 1640, Charlestown was given even more territory, extending its boundaries to include present-day Winchester, Woburn, Burlington, and Wilmington. This area was surveyed in 1638, and lots of land were granted to men of Charlestown, as recorded in the Book of Possessions. [Read more: Waterfield]

1890-puritansIn 1640, the first buildings in Winchester territory, Edward Converse’s house and grist mill, were built, and in the same year a committee was appointed to establish the bounds between Charlestown itself and a village. In 1642, the village, named Woburn, was established as the 12th town of the Bay Colony. At its south end a small settlement gradually developed around the early mills and tavern and became the core of the later town of Winchester.
(At right, men of Winchester dressed as Puritans for the settlement’s 250th Anniversary.)


The African slave trade began in the Massachusetts Bay Colony in 1637, a few years before any Englishman settled within Winchester boundaries. Up through the 1780s when the slave trade was abolished, very few households existed within those bounds. Large-scale slave-holding, such as practiced at Medford’s Royall House, did not exist here. Nevertheless, slaves were present within Winchester’s parent towns, Medford and Woburn. [Read more: Slavery in Winchester]

Records are currently lacking to tell how residents of the area stood on abolition during the years leading up to the Civil War. A story about one Winchester man’s activities in the 1860s suggests that residents held conflicting positions. [Read more:  Abolition and Emancipation, Abolitionst John A. Bolles,  and The Sculptor and the Abolitionist] Reports in The Middlesex Journal indicate that during the war years the practice of slavery was being denounced. The men of the Winchester Literary Society, which ran a lyceum series, invited Frederick Douglass to speak in Winchester’s Lyceum Hall in 1862. The hall was crowded and listened to with close attention, the audience occasionally heartily applauding some telling points.

It was not until after the Civil War, which broke out just a dozen years after Winchester was incorporated, that a free black presence in Winchester began to develop. While this was occurring, one resident’s story reveals contempt for the Southern view of blacks. [Read more: Richardson in the South]

Winchester's first African-American residents were often transitory. The first who settled here were reportedly welcomed into the community and enjoyed good reputations. [Read more: Winchester's Early Black Residents]

During the last decades of the 19th century, as other blacks moved from the South to Winchester, a community developed in the area of Swanton and Harvard streets. In 1893, they organized their own church, the Second Baptist Church, later called New Hope Baptist Church. [Read more: Winchester’s Black Community and OIiver Barksdale]

IGifford-schooln some ways, African-Americans were assimilated into the town, but they were not fully integrated into the town. The children attended non-segregated schools, but sometimes they experienced difficulties fitting in. [Read more: Jesse Anthony Powell and Truant Parents Allege Discrimination]

(At left, only one African-American child attended the Gifford School when this photo was taken.)

One place where young people were able to mix and prove their worth, no matter the national origin, was the athletic field. The ability to play ball was what mattered, though the option of turning pro was unfairly limited. [Read more: Branch Russell and Robbie Robinson]

During the world wars, Winchester’s African-Americans joined up. Particularly during World War II, entering the Army or Navy meant experiencing segregation practices not known at home. [Read more: African-American Veterans]

By the end of the war, more blacks were leaving their home town. In 1958, a Dartmouth College study reported that “Negroes have left Winchester, and no one seems to be encouraging them to return.”1 At the end of the 20th century, the number of Winchester’s blacks was about one percent of the population (about 200 people).

During the 1960s and 1970s, Winchester was caught up in the national civil rights movement. Debates over participating in METCO, which proposed busing inner city black children to school in the suburbs to counter racial imbalance, divided residents. The resignation of a black teacher in 1978, rumored to be racially motivated, prompted more attention being given to equal opportunity and racial sensitivity.

Meanwhile, the First Congregational Church opened a pre-school nursery for children from Roxbury, and St. Mary’s admitted black students as part of the archdiocese’s equal education program. In 1971, Winchester joined “A Better Chance,” a national nonprofit organization that provides academically talented scholars of color with expanded educational and career opportunities. Ten boys from every part of the country lived in the ABC house at 2 Dix Street. Through 2016, more than 85 scholars had graduated from Winchester High School.


Nationwide, the second wave of immigration (c. 1820-1870), included Irish, Germans, Scandinavians, and Chinese. The Irish particularly impacted Winchester. The Port of Boston being a major center of immigration, many made their way into the suburbs, including Winchester. They introduced not only ethnic diversity but also Roman-Catholicism into the Protestant town, provoking some opposition and controversies. [Read more: No-Nothings]

Irish had been around since at least the 1860s. At least 18 of the Civil War volunteers credited to Winchester were natives of Ireland. Most of the Irish during the early 20th century were Irish-American. Like the Canadians, the second largest component of English-speaking nationalities, the Irish were assimilated into the town more easily than immigrants not speaking English. Many worked in construction and others in municipal service, especially the Fire and Police Departments, and they were elected to town boards. Many of the Irish settled to the north of the town center, where there was once a Shamrock Street (now Spruce Street.)


Italians, who came late in the third wave of immigration (c. 1880-1914), also settled in the northern section of town, along with the Irish and African-Americans. Early Italian immigrants worked on the farms but also found work in the factories or with industries which could use men with skills such as stone or leather working.

Since the town’s Catholics were also its Irish and Italians, “the socio-economic cleavage in the Winchester population [was] thus accompanied in part by religious and educational differences."2 The Irish and Italians, though both predominantly Catholic, did not always mix well. According to one study, the Irish already settled in town resented the increasing number of “foreigners” moving into town, and the Italians resented the Irish resistance and their domination of the church.3 The Irish and Italians had separate social organizations, including the Ancient Order of Hibernians for the former and a lodge of the Sons of Italy and Christopher Columbus club for the latter.

Although the whole community could enjoy the Feast of the Assumption celebrations, the Italians did not mix on an equal footing with the Yankees for many decades. Not until 1950 was a resident of Italian heritage elected to the Board of Selectmen.

A surge of interest in assimilating as Americans arose among Italians during World War II. With many of their sons joining the military, parents took steps to citizenship such as attending the Americanization classes which the Town offered. “Before the war is over it is safe to say that we will have very few non-citizens of Italian extraction in Winchester. It is very gratifying to feel that their lack of citizenship papers does not mean that they are not loyal, upright Americans in every respect.”4 It helped considerably that the government lifted the stigma of “enemy alien” from Italian non-citizens in 1942.5

Though not as numerous as the Italians or Irish, another noteworthy nationality arrived in Winchester during the third wave, Russian Jewish refugees. Few of these families remained in Winchester beyond a second generation, their small presence pointing up a long-standing prejudice through the end of the twentieth century. [Read more: Russian Jews]

While many immigrants settled into communities within the town (mostly in areas known as The Plains and the North End), some found positions on household staffs, meaning a search for Winchester’s diversity might easily take one to any street where domestic help was needed. [Read more: Help Wanted] Others were transient laborers, occasionally being recorded by a census or other record, adding to the ethnic mix, but soon moving on. [Read more: The Latvian Revolutionary]


According to the 1900 census, the largest populations of foreign-born residents in Winchester were Irish, Canadian, English, Swedes, and Italians. Ten years later, the number of Italian-born had quadrupled, though Irish-born residents were twice as numerous. While the Irish and Italians continued to be large ethnic minorities, small numbers of other European nationalities appear in the censuses through 1940, but few numbered more than ten.

In 1913, when an evening school to teach English to foreign-born residents began, Initial registration included 106 Italians, 8 Turks, 3 Swedes, and 2 Greeks. In the second year, there were 77 Italians and 8 Swedes. In 1915, students were mostly Italian with a few Germans and Swedes. The School Department not only offered them English instruction but also Americanization classes (e.g., American history and civics).

A 1921 study by the Department of the Interior 6 disclosed that in 1919 forty percent of the fathers of public-school children were foreign born. Nineteen countries were represented – Austria, Brazil, Canada, Denmark, England, Finland, France, Germany, India, Ireland, Italy, Mexico, Norway, Poland, Portugal, Russia, Scotland, Sweden, and the West Indies.

When World War II broke out, the ethnicity of Winchester service people ran through a wide range of nationalities – Scandinavian, Italian, Greek, Armenian, Turkish, and others – but all Americans.

Asian people were few in Winchester until the end of the twentieth-century. At the beginning of the 20th century, there was a Chinese laundry, but, according to one newspaper story, fear of competition kept others away. Japanese residents were unknown through most of the twentieth century. When the twenty-first century arrived, however, it was apparent that the Asian population was the fastest growing. [Read more: China Connections]


Newcomers to town during the nineteenth and twentieth centuries also included native Americans from other areas of the country. Quite a few families and individuals from Maine, Vermont, and New Hampshire, plus other Massachusetts communities, gravitated to the towns circling Boston. The story of one such, Samuel Twombly, is the stuff of which the American dream was made, as he progressed from humble beginnings to an honored place in society, entertained at no less a home than the White House. [Read more: Samuel Walker Twombly]

Center-depotMany of the people whose move into Winchester stimulated its transformation from a community of farmers to a suburban town were the families of business and professional men who could use the railroad to commute to work in Boston or Lowell and also have the advantages of rural or suburban living. Thus, in 1873, one historian wrote that “The inhabitants are mostly of a highly respectable character, many of them doing business in Boston. From Boston, therefore, they derive largely their manners and customs."(Left, commuters await the train at the center railroad depot.) 


It was not just nationalities which defined groups and identities within the town. When Winchester was young and the population was small, its churches provided for social interaction but also created social divisions as people clustered within their various sects. During the later 19th century, the introduction of organizations like the Village Improvement Society and The Fortnightly women’s club brought like-minded people together over interests and causes which overcame differences of creed. Some minorities formed their own organizations to support their own. But many club memberships were diverse. Clubs were formed for sport or entertainment. Other organizations were founded to improve the town, assist business, support education, and provide charitable service to less fortunate residents. The spirit of volunteerism became a hallmark of the town despite its social divisions. 


As early as 1842, when Rev. William T. Eustis was minister at the South Woburn Congregational Church, “the village and the parish was popularly divided into the farmers on the west side, the manufacturers in the village and the car-riders, each a clique by themselves.”By the end of the century, cliques were separated not just by occupation but by wealth.

In a college paper written in 1917, Elizabeth Lord Kneeland commented on a significant social change at the turn of the 20th century. “Quoting the words of Governor McCall in his oration on the 250th Anniversary of the first white settlement in Winchester [1890]: ‘The town has few very rich or very poor, but the inhabitants belong to a more favored class who are neither consumed by idleness on one hand nor anxiety for existence on the other hand, and whose enjoyment of life is stimulated by remunerative toil.’

Tolley“In the twenty-five years since this speech, the town has changed very much in its character. People of wealth and standing have taken up their residence in the town, and it has become a residential suburb of Boston. On the other hand, homes for industrial workers were built over a dozen years ago in one section…an inducement for people to settle on account of cheap rents, and their nearness to the present manufacturing plants.”9

(Like the railroad, trolleys contributed to Winchester’s popularity as a residential suburb.)

As Kneeland observed, the village of farmers, shopkeepers, and industrialists gained more wealthy families–and a tiered social structureas it moved into the 20th century. The prosperous continued to transform the town, even issuing a “Prosperity Proclamation” in the Winchester Star in 1900, signed by 63 distinguished men of the town, designed to attract more of their social class. 

“In Winchester we have a home town, beautiful, healthful and well governed, one of the best places in the world to live. 

“Winchester is one of the most desirable suburbs of Boston, near enough to enjoy all the advantages of the metropolis and yet far enough away to avoid the unpleasant features of a great city.

“Because of the many advantages Winchester has to offer, combined with the thrift, intelligence, and patriotism of our people, we hereby express our confidence that Winchester’s future will be more glorious than her historic past or prosperous present, and that greater population, increasing prosperity, and progress along all lines will be the portion of Winchester for many years to come.”10

People of means contributed greatly to the town. “When I joined the police force [1938],” Police Chief Edward F. Bowler, a native Irishman, said, “Winchester was a Yankee town. It was run by the Yankees. They built the town up. They erected most of the public buildings such as the town hall, the police station, the fire station, the high school which is now called the Lincoln School. They built up the reservoir system. They built the parks and playgrounds.… they were the ones who got [the town] heading in the right direction.… They really had public spirit. They loved the town and wanted to do something for the town, and they did a lot. A lot of those people were what you would call millionaires today. They were real big businessmen from the city. They weren’t too busy to contribute their time to the town.”11

Piano-case-millHowever, in their zeal to create a picture-perfect bedroom community, particularly their vision of a Winchester without large industry polluting the air, land, and water, they managed to create a division between the white- and blue-collar elements of the population. Farmers, especially descendants of the old farming families, were always respected members of society, elected to town offices and welcomed into local organizations. However, factory laborers (such as those shown at the Cowdery, Cobb & Nichols piano case factory, right) were another matter. [Read more: Industry Debated]

The distinction between industrial and residential Winchester disappeared during the 20th century as heavy industry was zoned out and as residents’ occupations and backgrounds led to a much more diversified society. However, the town still retains neighborhoods with characteristics inherited from former residents’ economic status.

The architectural history and artistic heritage of the town are all the richer for the wealth of the residents. Town betterments and causes benefited from it. Though the Great Depression marked the end of one era of great estates, prosperity is still a hallmark feature of the town. However, a mix of ethnicity, income, occupation, and education within the town–along with a mix of opinions about the future of the town–survives.


The names of many individual persons have been memorialized in the name of a building, field, or other location. For a list of names of places, see this guide to Winchester Place Names. See also an Eagle Scout project on Winchester’s Historic, Commemorative Memorial Signs & Markers.

For many noteworthy individual residents, see also the section on Renowned Residents. 


1. “The Winchester Study,” a typescript report of an opinion survey undertaken by Dartmouth undergraduates, c. 1960, for use in Sociology I lab.
2. John Guy Fowlkes, “Winchester Looks at its School,” typed report, 1944.
3. “The Winchester Study."
4. Sons of Italy column, The Winchester Star, Nov. 20, 1942.
5. According to the Sons of Italy, as published in The Winchester Star, Nov. 20, 1942, the change was due to the efforts of Woburn’s Joseph Gorrasi, Grand Venerable of the Grand Lodge of Massachusetts from 1939 to 1946.
6. Survey of the Schools of Winchester Massachusetts. Washington, Government Printing Office, 1921.
7. John Adams Vinton, The Symmes Memorial, 1878, p. 155.
8. Letter from William T. Eustis in Springfield to Rev. George Cooke, Jan. 15, 1887.]
9. Elizabeth Lord Kneeland, “A Study of the Social Forces in Winchester,” December 1917, likely written for her course in social work at Simmons College.
10. The Winchester Star Home Number, Dec. 16, 1910.
11. Interview of Edward F. Bowler by Herbert Edmonds, June 1980.