For two centuries prior to incorporation, the area which is now Winchester was rural territory lying within Woburn, Charlestown, and (beginning in 1753) Medford. The land was divided into large farms, with a few mills and home industries. 

In 1850, during its gradual transformation from a village to a suburb, it became an independent town. Its population grew due to its proximity to Boston, its industries, and its appeal as a residential community. Winchester today (2018) is primarily a bedroom community with a population of over 21,000. [Population Statistics]

Winchester lies in the Mystic Valley north of Boston, an area of abundant water which both enabled the cultivation of its land and provided power for the first mills.

1794 mapComposite of maps of Charlestown and Woburn from 1794, showing what would become Winchester, feature the water bodies, Horn Pond Mountain, the Great Road, and the site of the first mill in the center.

The area was connected to points north and south via the Great Road (Main Street) and during the late 18th and early 19th centuries provided a stop on stagecoach routes, the Black Horse Tavern, but it was not until the construction of the  Middlesex Canal and especially the Boston and Lowell Railroad in the early 19th century that the population began to grow markedly and the settlement began to develop a village center and its own identity, despite its territory belonging to three separate towns.

With the nineteenth century came an era of industrialization. This was a time of considerable expansion for the community. A survey of South Woburn made in 1831 listed sixty dwellings, almost double from 1798. After the railroad opened in 1835, a number of new businesses were founded, many businessmen and workers moved here, and the population steadily rose. During this era, Winchester was incorporated. The population was then 1,350.

Winchester SquareFollowing incorporation, several public buildings were erected in the town center which provided retail space and meeting rooms for an increasing number of community groups and activities, (such as the Lyceum and Brown & Stanton Buildings pictured right). Winchester became a popular suburban residential community for those working in Boston, and its industries brought an influx of immigrant workers. As the population continued to expand in the latter part of the nineteenth century, residential development began to replace the old farms.

“Old ways are closed up, new avenues lead to higher civilization and broader life. The world moves, and Winchester is in the front rank,” said Nathaniel Richardson who had been born in South Woburn and watched the little village transformed.1 

Looking back in 1900, Richardson said, “Fifty years ago Winchester was a small village with a few plain dwellings, crooked and ill constructed streets, two small school houses, one meeting house, the aspect of the town simple and rural; to-day it is inviting and impressive in every feature, imposing homes, magnificent in style and comfort, with fine lawns picturesque with flowers and shrubs. Six churches…. Eight school houses… Streets wide and costly built, taste and beauty respond to the wish of the people, growth and prosperity are developed with marvelous advance.”2

From the 1890s through the twentieth century, the trend toward suburbia led to the closure of heavy industries and limitations on new light industries, leaving the town primarily a residential community. Richardson might not recognize Winchester today. However, within modern Winchester is a range of architecture documenting its life as a town that has been home to farmers, industrial workers, commuters, affluent families, social and political leaders, and artists. 


Today’s Winchester Center surrounds the Mill Pond created by the first settler, Edward Converse. A leader in the establishment of the town of Woburn, Converse built a home and a grist mill by the Aberjona River. In that early era, however, other businesses did not locate around this mill. Maps from the early 1830s show that there were clusters of buildings in other places than what is now Winchester center. Around the Bacon mills near Mystic Lake, for example, there was a little cluster with homes for the mill owners and the mill users. There was employment there; there were houses here. The area became known as Baconville, but it did not develop as a commercial center - nor did any other mill site.

Black Horse TavernIn the eighteenth and early nineteenth centuries, a tiny commercial center formed around the Black Horse Tavern. “No spot in Middlesex County is more historical in all its narrative than this once famous tavern,” Nathaniel Richardson declared in 1900. It history began in the 1720s, when “a mansion house” was built. From the 1740s (or earlier) it operated as a hostelry known as the Black Horse Tavern. Located on Main Street not far from the juncture with Washington Street, it was a favorite stopping place for travelers. In the 1790s, it was on the stagecoach routes from Boston to Portsmouth, New Hampshire, and Portland, Maine, and the area was frequently called Black Horse Village.  [Read more: Black Horse Tavern]

“This tavern was formerly in great repute for its excellent suppers,” it was written in 1885, “and it was a favorite drive with the Bostonians to the Black Horse and back, including the supper.”3  But the tavern was not just a place to quench the thirst. It was a meeting place. If there were meetings during the Revolutionary War, the tavern was the place for them. The first singing-school met there before the church was built, and it was the headquarters for the first Winchester band.4 

Nearby there was a blacksmith shop. At the junction of Main and Washington Streets, Paul Wyman and his son Jesse operated the first known store from about 1775 to 1840. Across from the smithy, in 1825, the Grammer brothers, William and Seth, built a store near the junction of Main & Washington on the west side of Main (near the present-day classroom wing of McCall Middle School). It was called an “English and West India Goods Store.” Goods for sale included salt fish, oil and molasses; sugar, tea, and coffee; pepper, cinnamon, cloves and allspice; plus rum, brandy, gin, and wine. Near it was a sash and blind factory run by steam power. Another store was built on the opposite side of the street a little north of the Sharon House. There were also some residences, including one which was named “Lamb Tavern” though it was simply a dwelling house.  [Read more: Lamb Tavern]

The first Liberty Pole in the village was raised at the junction of Main and Washington Streets near the blacksmith shop in 1826. “It was quite an elaborate affair with main-mast, cross-trees and top-mast.”5   But when the second Liberty Pole was erected in 1862, it was placed at the new center of commerce by the railroad crossing at Main and Church Streets.


A few decades before Winchester was incorporated, a village center had begun developing around the Converse mill pond created by Edward Converse. But, back in the 1820s, the old Converse mill, then owned by Abel Richardson, was in a decline. It had actually gone to decay. The Cutter mill on Horn Pond Brook was only grinding corn for local convenience. There was only one blacksmith shop and one wheelwright shop. There were a succession of shoe shops attached or next to homes along Washington Street, as well as Main Street, Church Street, and Cambridge Street. South Woburn was not a business center.

What changed that was the railroad. In 1835, South Woburn got a railroad line, not because it was an important destination, but because it happened to lie between Boston and Lowell. In the late 19th century, Oliver R. Clark wrote “The original scheme of the railway connecting Boston and Lowell did not appear to contemplate any provision for business at this point, so the building first used as a station was a small shoemaker’s shop, about 10x15, which answered every purpose till the increasing size of the village rendered a larger building necessary.” For two years after the opening of the railroad, Clark wrote, only a few changes were observed. But then there came a man whose eagle eye saw the advantages of that spot as a good locality for business and the founding of a new town.

That person was Samuel Steele (“S.S.”) Richardson. Having already established a prosperous shoe-making business in Woburn and seeing the possibilities of South Woburn at the site of the railroad stop, he bought the old Converse/Abel Richardson mill site, rebuilt the mill, built several houses, and a new shoe shop. He bought the Black Horse Tavern site. He overextended himself. The Panic of 1837 (a major recession which lasted nearly a decade) left him financially embarrassed, which might have been the undoing of the fledgling village, but then Benjamin F. Thompson moved from Woburn to South Woburn. He purchased land and built a tannery down at the end of Thompson Street, creating jobs. He lived first at the corner of Main and Thompson Streets. He then bought the Converse/Richardson home site and built a new house.
AR Mill Pond watercolorHarrison Parker, who married a Richardson, took over the old Richardson mill near the Woburn line, then bought the Converse/Richardson mill site from S.S. Richardson, moved his business there and was very successful, and created more jobs. From 1845, he shared the mill with Joel Whitney who ran a machine shop there, and also prospered.

An anonymous watercolor of Mill Pond c. 1900

The jobs available at these sites and the Cutter mills just up the street attracted people to South Woburn, as did the convenience of having a country home near a railroad stop of the Boston train. As the population grew, more stores were needed. The U.S. postal department opened a post office here in 1841. The first physician known to settle here arrived in 1846 and settled on Thompson Street.  [Read more: Development of the Village Center]


With the village of South Woburn growing and developing as a community, a movement for independence grew. 

Although the first house in the Winchester-Woburn area was built in Winchester, the site chosen for the community church was situated in Woburn. For about two centuries much of land now encompassed by Winchester's boundaries was part of Woburn and designated South Woburn. For two centuries the area south of South Woburn remained part of Charlestown. The eastern section of that was annexed to Medford in 1753. The western part briefly belonged to West Cambridge (now Arlington). 

PiperThe advent of the railroad and the consequent industrialization of the community spurred the growth of the village of South Woburn (pictured right c. 1845). The village took the first earnest step towards independence in 1840 by establishing the First Congregation Society of South Woburn. Political differences between the village and Woburn and wrangling over municipal spending led, nine years later, to earnest talk on incorporating a new town. Though not universally favored by those who lived within the proposed boundaries of the town, it was championed by the majority. The Town of Winchester was incorporated in 1850. [Read more: Steps to Incorporation]

Prior to submitting a bill for incorporation to the Commonwealth, a name had to be chosen. After a vote on a name failed to settle the choice, the committee acted on a suggestion to name the town for a man of wealth who would reward the town for the honor. Thus, the town was named for William Parsons Winchester, a merchant of Boston, who died in the same year the town was born and never set foot in it. [Read more: Naming the TownCol. William Winchesterand Named for Winchester.]


After 1850, Winchester was steadily built up, and its development as a Victorian town remains visible in its architecture today, including its Center. At the time of incorporation, the buildings that housed shops around the railroad stop were small, wood-frame buildings, including houses converted to business use. Benjamin Thompson’s sons, in fact, turned his house into a business building by raising it up over a new first floor, making it a commercial building.  

LyceumIn 1851, a number of men of the community who thought that the town should have a space for public, secular meetings and functions provided the funding to build Lyceum Hall (pictured left c. 1871). It accommodated shops in the basement, stores on the ground level and a hall which could be divided by folding doors, above which was the main hall and four offices, over which was another hall and office or committee rooms. Town Meeting used to meet there. Several eminent speakers, like Oliver Wendell Holmes, participated in a Lyceum series, and a young Teddy Roosevelt came to stump for the Republican ticket in 1884.  [Read more: Teddy Roosevelt in Winchester]

Another large wooden building was the Kelley & Hawes livery stable, demolished as recently as 2001. Some other old wooden buildings survive today. However, beginning in the 1880s, the next significant step in developing the Center was to build in brick and stone. The first of these sturdy buildings was the RichardSavings-Bankson Block at 607 Main Street, built in 1872 by Sumner Richardson. Like the Lyceum Building, it was a building for mixed use. The tallest building in town, it had three floors and a large hall at the top, the site of dancing parties and meetings of social and fraternal organizations. The building later (about 1897) became the Hotel Winchester.6  Before its conversion to a hotel, the Town Library was located on the second floor, until it moved to the Brown & Stanton Building, built in 1886. This building also had shops, offices, and a hall above. Others substantial business buildings followed, the White Building, the White Block of 1890, the Savings Bank in 1892 (pictured), and Richardson Building on Mt. Vernon Street in 1893. [Read more: Kelley & HawesHotel Winchester.]


A view of the Center from Rangeley (left) to the Town Hall (right) c. 1895

Civic buildings were raised in the Center. In 1887, a Town Hall and Library building was built next to the northern end of Mill Pond. The police station was in its basement. The Fire Station (first a wooden structure) was on Winchester Place. Although the first high school building was at School Street, when the time came for a new one, it opened in 1904 on a hill overlooking Mill Pond. And when a separate library building was constructed in 1931, it also overlooked the pond. The new Public Safety Building was constructed across from the pond. [Read more: Town HallPublic LibraryPublic Safety Building]

Main Street businessesNot every building built at the end of the 19th century was big, tall, or substantial. Next to the Brown & Stanton Block was the two-story Lieberman Block. Moving into the next century, in 1913 the Lane Building was built on Church Street and in 1914 the wooden Morrill building was demolished to make room for the Star Building. Two stories were enough, since there was no longer a need to create space for meeting halls. (Left: The Brown & Stanton, Lieberman, and Thompson buildings on Main Street)

With the population growing, the town got a new depot in 1872, located on the south edge of the downtown business district (where an even newer one stands today). It was one of four stations (the others at Wedgemere, Highlands, and Cross Street) used by commuters. Local industry also relied on the railroad and several had railroad sidings for their freight. Trains, including long freight trains, passing back and forth through the town were a common sight, as well as a constant danger to pedestrians downtown. [Read more: Waterfield Lot and Center Train Station, The Evolution of Winchester's Four Railroad Depots, and Murder at the Depot]


Although industry was the making of the village of South Woburn and early town of Winchester, the time came when it was ousted from the town center and other parts of town. Along the river, in the place of factories, the Town created parks. 

The first landscaped public area in town was Wildwood Cemetery. The money Col. Winchester gave to the town was used to purchase the property (and was paid back through the sale of lots). Amasa Farrier of Stoneham designed the original plan of lots, carriage-ways, and footpaths. [Read more: Wildwood Cemetery]

Common-1905In 1867, the Town purchased the lot across from the First Congregational Church. Two years after a bandstand was erected there in 1873, an appropriation was voted for landscaping it into a place to be enjoyed as the Town Common. But at first little happened. [Read more: Town Common]

Improvements got a boost from the citizenry. In 1882, the Village Improvement Society was organized. Interested in the care and beautification of the town, it focused early on the Common. Under its influence, the next Town Meeting established a Committee on the Common and gave it money to improve the area. The Society promoted tree-planting, so a Tree Committee was formed and a Tree Warden appointed. “To the efforts of the association also we owe the establishment of a tradition of well-cared for lawns and private grounds, which has made Winchester one of the most attractive towns in the state.”7 

coal and wood yardThe creation of more parks accompanied the river improvement program, which began with Mystic Valley Parkway in the 1890s and lasted through the 1930s. It resulted in Ginn Field, Manchester Field, Shore Road Field (now site of the high school), Davidson Park, and the Washington Street Park. The parks were created to prevent the return of river-side, polluting industries, provide flood-expansion areas, and to develop a green ribbon through the town. [Read more: Aberjona River]  (Right: the wood and coal yards formerly at the site of Manchester Field and, below, the original field with its bandstand)

Parks were not confined to the riverside. Though never developed for active recreation, a gift in 1913Manchester Field bandstand provided for the Irving S. Palmer Field at Palmer and Middlesex streets, although it was never developed as a playground or sports field. Rather, the town invested, in 1917, in the land where it built tennis courts and, in 1929, a strip of land on Main Street adjacent to Wedge Pond later (1966) the site of Elliott Park. The most recently created public park is Bellino Park on north Main Street, dedicated in 2004. Several fields, such as Leonard Field, were created for school and community sports.

While the population boomed and more land was divided for house lots, other areas preserved for the enjoyment of the citizenry and the protection of native species, include the conservation areas, the Town Forest, and Locke Farm. [Read more: Town Forest]


The earliest home building quite naturally occurred along the major thoroughfares. The first road, the Great Road, connected Medford and Woburn along what are now Grove and Main streets, though it was soon laid out to follow Main Street’s current course. Cambridge, Church, and Washington Streets were other early roads. The main roads shown on the first map of Winchester, drawn in 1854, designate where the early habitations were. Those that were accepted public ways were Main, Washington, Forest, Cross, Pleasant, Pond, Bacon, Grove, Church, Cambridge, High, and Fruit (now Hutchinson).

Tenant housing Cutting StreetAs the farms spread over large acreage, the earliest neighborhoods were the clusters of homes around industries, like Baconville and Cutter Village. Homes built for workers still survive in areas where there were factories. (Right: former tenant housing on Cutting Street)

Skillings-tower-houseAs Winchester became increasingly residential, other neighborhoods were formed by developers who subdivided old farm land for housing. One remarkable development was Rangeley, owned by David Nelson Skillings who planned a park-like setting and chose an architect to design homes for professional gentlemen and their families whom he wanted as neighbors. While he and next owner Edwin Ginn lived, it was a country estate in the center of Winchester. (Left, Skillings' own tower house.)

Several other developments carved up the valley sections of Winchester in the latter part of the 19th century. The Wyman Plains north of Church Street (a.k.a The Flats), though once considered “remote and undesirable for residences,”8 was laid out for houses lots in 1891. Despite some setbacks, over 90 Victorian homes were raised in the Wedgemere district. Smaller in scope, but also successful, was the Firth Development, where local architect Robert Coit designed a number of middle-class homes. Striking architecture is a noteworthy element of the third major development, Everett Avenue, where homes were designed for more prosperous residents. All three of these districts have been on the National Register since 1989. Picturesque Winchester

Different areas of town acquired different characters based on the social status of the residents. By the early 20th century, the west side of town – which did not yet include the Hill – was inhabited by the Yankees, the white-collar professionals, the most prosperous families of the town. The East side of town lay to the east of Main and Washington Streets. The Highlands was centered on the intersection of Washington and Cross streets, though the name “The Plains” lasted longer for the area between the railroad and Washington Street, north of the high school site. The term “North End” has been applied both to north Main Street and the area between Main and Washington Streets. In The Plains and the North End of Main Street, industry persisted longer than in the center, and those areas contained the most worker’s housing and the most ethnic minorities. Another name, which has dropped out of use, is “The Bowery” for the area around Main and Lake Streets where there was a tannery and a series of houses for the tannery workers.

“The railroad tracks really divided Winchester,” Mildred Newell (1912-2011) recalled.  “There was a little funny feeling between the two sides, and it wasn’t until you went to Wadleigh [Grammar] School that you mingled with the kids from the other side of the track.”9 

Harvard-Street-GardenLooking back in 1955 to his childhood, Robert E. Sanborn (1905-1984) commented, “Then, as now, there was the ‘West side,’ whose residents were reputed to spend money and there was very evidence that they did, and the ‘East Side’ whose residents meticulously paid their bills, and lived and looked like the solid conservative citizens that they were. The West side looked down its nose at the East Side, and the East Side looked askance at the extravagance of the West Side…. Both East and West Sides were extremely condescending toward the inhabitants [of The Plains.] They were poor, Irish and Italian immigrants, tannery and farm workers.” (Pictured is a view from a Harvard Street garden)

The poor of about 1912, Sanborn said, suffered from “a combination of low wages, liquor, large families, and wretched housing” but benefitted from many charitable acts. By 1955, he added, the situation was wholly different.10  A 1944 study of the school system agreed, stating that although those in the Plains had a lower income they were still prosperous. “The residents of the plains area largely conduct the local business, do the necessary work within the community and furnish laborers for the one major local industry, the tannery. In this part of the town there are important racial groups of Italians, Irish, and Negroes. There is a conscious effort on the part of the residents of the hills areas of the town to confine these families to the plain, but they tend to encroach upon the adjacent hills as family income rises. The effort is to reserve the hills for older residents of good income employed largely in Boston in important executive and professional positions.”11 

McCall mansionAs less land in the valley area of Winchester was available to be subdivided and as automobiles were making access to the hills easier, the hills on both east and west sides began to see some development. In the first decade of the 20th century, Samuel McCall (later governor) and George Fernald built their own homes and laid out other building lots on Myopia Hill. Prominent and wealthy men like Handel Pond, Jere Downs, and Oren Sanborn built mansions in other areas of the west-side hills. (Right: the McCall Mansion) [Read More: Myopia Hill]

In the 1920s, 660 new homes were built in town, accounting for about one-fifth of the total dwelling units in 1930. New growth in the 1930s occurred mostly on the slopes of the Middlesex Fells and the eastern part of the western hills, though farms still occupied the Ridge Street area. There was also growth around Wedge Pond and the Mystic Lake. By the end of the decade, there were 528 new dwelling units. In the 1940s, 591 new dwellings were added, mostly in southeast and western Winchester.12 

By then, the Ridge Street area was the only one not intensively built up with houses. However, with a post-war housing boom and people leaving off farming, the latter part of the 20th century saw this area developed. 

The latter part of the 20th century saw many social distinctions and barriers break down (though not entirely).13  Still, the town’s various neighborhoods retain distinctive qualities related to their early development.


In 1915, the very first Planning Board was elected. One of its first priorities was to collect data on which to base a plan for future development, for the town was indeed developing. The first set of Zoning Bylaws and a Zoning Map appeared in 1924. A Building Department was added to oversee compliance with both state codes and local zoning. Various changes to the zoning have occurred over time.

A Master Plan was developed in 1953 which focused on development of the west side. Not until 2010 did a new Master Plan begin to roll out, with Part I reporting on housing, neighborhoods, town center, and economic development. As the town is essentially built out, the focus in this plan and the new Master Plan currently underway (as of 2018) is on redevelopment.


In 1986, many architectural achievements of Winchester’s past were recognized when Winchester Center became a National Register Historic District. However, while much historic architecture has been preserved, the Town Center has continued to evolve. The demolition of the Hotel Winchester (1941) and major fires which took the upper floors of the Lyceum Building (1950) and White Building (1951) and destroyed the Waterfield Building (1961) reduced the overall building height downtown. Some building façades changed with alterations in architectural aesthetics or new uses. The one industry which survived in the center, the Winchester Laundry, was transformed into an office building in 1973.]  Some old buildings were replaced, as when the Fire Department moved into a sturdy brick building in 1915. Others were removed to make way for new ones, like the Post Office of 1928. Expansion of the high and junior high schools and the library took several old residences out of the civic center.

In the latter part of the 20th century, dwindling open space only rarely allowed construction on new sites. The 1971 high school was constructed on the former Shore Road Field (formerly the northern end of Judkins Pond). The Jenks Senior Center was built on land which the Town bought in 1943, leveled for the construction of the Skillings Bypass in 1956, and used for a parking lot.

Train at gradeThe greatest physical change occurred in the 1950s with the erection of the railroad viaduct or overpass. Trains crossing at grade through the intersection of Main, Church, Mount Vernon, and Shore Roads, had always been dangerous. For decades townspeople and boards examined plans and debated what to do. Not only a safety issue, it was wrapped up with plans to improve the civic center. The eventual solution was the erection of an overpass which opened in 1956. Though safer, it also created a great wall dividing the downtown. [Read more: The Railroad Overpass]

Like the railroad, automobiles also posed problems. At the same time the overpass was created, Skillings Road was added as a way to bypass the Center. Still, dealing with ever increasing traffic has been a major challenge. Different schemes for parking meters and lots have been employed. Studies have been made for a public parking garage, though one has yet to be enacted. [Read more: First Automobiles Made News in TownAutomobile Era]


“Before the town renovated Winchester’s Town center,” former selectman Ed O’Connell recalled, “the center unfortunately had lost some of its glamour and some of its shops that were the real attraction of Winchester. At one time, for example, we had in Winchester Center a small version of Filene’s. People would come to Winchester from other communities just to shop at Filene’s. We had our own Brigham’s ice cream shop. There was a woman who owned a children’s shop and it was spectacular, but that too has faded out. The downtown area was unfortunately going through an unhealthy number of empty stores. We really did a major overhaul with new sidewalks, new street lamps and much more attractive additions than whatever had been there before the remodeling of the downtown area. I think that we’ve probably rescued the town from an almost unhealthy clearing out of good shops. Most residents were supportive of that. Everyone wanted a change. We were going to do it, and we did it right.”14 

Both the 20th and 21st centuries have seen Center revitalization programs, focused on improving the business economy and, in the latter case, Smart Growth.  In 1972, during an era when malls were attracting customers, the Board of Selectmen received a study (the Robert Oppenheimer Plan), met with the Winchester Business Association, and formed an ad hoc Center Committee to make recommendations concerning the future of the Center. In 1982, the Winchester Economic Development Committee issued a program for center revitalization (the one O’Connell noted). In 2009, in connection with its new Master Plan, the Planning Board in conjunction with the Board of Selectman undertook studies and community conversations on downtown revitalization in order to re-examine and change the Zoning Bylaw to promote residential and commercial uses in the Center.


Winchester is essentially built out. Thus, new construction generally takes the form of redevelopment. Redevelopment proposals and activities have often clashed with residents’ interests in preserving the built character and natural environment of their neighborhoods.

For example, residents have consistently opposed Ch. 40B developments. In 2016, the Zoning Board of Appeal approved a Ch. 40B project for Cambridge Street called Winchester North, subsequently appealed. Proposals for other Ch.40B projects have followed. A proposal to build a 40B apartment complex off Forest Circle and a proposal to develop a lot between Highland Avenue and North Border Road both failed. Other proposals are in development.

Other housing issues in the 21st century include tear-downs, mansionization, affordable housing, and the need for moderately priced homes. 


In 1901, life-long resident Nathaniel A. Richardson reported on a conversation he had with the grandson of John Quincy Adams, writing that Charles Francis Adams said “he regarded Winchester as one of the most beautiful and desirable towns outside of Boston, whichever direction one might go. I told him some of the towns south of Boston are thought to be more pleasing and popular.  He said, ‘No, they are not’ Winchester is equal or above them all in its scenery, location, and progress.”  

“I was impressed with the town right from the beginning (1956),” resident Bob Gallant said. “We loved the school system, and we figured it was right up on the top of list as far as education was concerned. It was a typical bedroom community that had enough businesses in town that could meet our needs and had good transportation. One of the reasons why we moved to Winchester, because of the excellent train service that has always existed from Winchester to Boston. And at the time there was bus service as well. We have always been a one-car family. If I took the car, that left my wife with two small children and without any means of transportation. So it was much to our advantage to have a facility like the trains or buses for me to get into Boston. She would drive me down to the train station or the bus station, whatever it was, and then she had the car. And we thought it was a very attractive community, plus one that was reasonably affordable.”

The railroad, the schools, the attractiveness still draw residents. But other things have changed.

“And one of the things that attracted us to Winchester was,” Gallant continued, “it was countrified. There was a lot of open space. What we had in back of us was an apple orchard with one or two cows that were tethered. And that made it kind of a bucolic setting. As a matter of fact, in the whole town there was a lot more open space than there is now.  There was no Skillings bypass and, of course, the new high school hadn’t been built. There was no supermarket, no Jenks Center. There was the Town Hall and across the street was open land. And that was true all around town. Out High Street as far as Ridge Street, it was all farmland. St. Eulalia’s wasn’t there, nothing was there, just one house where the farmer owners lived. The shopping center along Cambridge Street, the Ledges, the Gables, all of that was open land.  It was just like driving through the country. But now it’s all changed.” For these and other reasons, he concluded, “I still like the town, but it’s different from what it used to be.”  

Through all its history, the town has grown and changed. Today it continues to change, and long-time residents still voice regrets over perceived loss. Still, it continues to appeal.15 

Envision Winchester wrote an idyllic description in 2002: “Winchester is a charming town distinguished by its appealing panorama of residential neighborhoods, rich architecture, and vital town center. Adorned by a ribbon of serene parks, forests, and waterways, Winchester is an engaging community enriched by its proximity to Boston, its accessibility to greater New England and its tradition of exceptional education.”16 

In 2017, Boston Magazine chose Winchester as one of the “Best Places to Live North of Boston.” In 2018, the Boston Globe ranked Winchester second after Cambridge among top spots to live with a $1 million-plus price point. “Winchester is a desirable place to call home — if you can afford it.”17 


1. Nathaniel A. Richardson, “Winchester’s 50th Anniversary,” The Winchester Star, April 30, 1900.
2. Ibid.
3. Oliver R. Clark, “Reminiscences of South Woburn, 1839-1839,” Winchester Record, Vol I, No. 3, (1885) p. 127.
4. A second tavern operated at the end of the 18th century in the old Belknap house on the other side of the village by Horn Pond Brook, but it apparently did not play as significant a role as the Black Horse Tavern.
5. David Youngman in an 1888 article quoted in The Winchester Star, June 5, 1975.
6. In May 1852, the Legislature made Frederick O. Prince, Oliver R. Clark, and S. S. Richardson a corporation by the name “The Proprietors of the Winchester House,” for the purpose of erecting a hotel or boarding house in the town. Apparently, although some boarding houses did operate in late 19th-century Winchester, it had to wait for a hotel until the 1890s. Statutes of Massachusetts, 1852, Ch. 309.
7. Henry Smith Chapman, History of Winchester Massachusetts, p. 264.
8. The Winchester Star, May 31, 1901, William Boynton obituary.
9. Interview of Mildred Johnson Newell by Selina Woods, July 15, 2004.
10. Robert E. Sanborn, “Recollections of Winchester, Mass.,” typescript, [1955].
11. John Guy Fowlkes, “Winchester Looks at its Schools,” typed report, 1944.
12. Statistics from William A. Withington, “The impact of Residential Growth on Land Use in a Suburb, 1930 to 1950, Winchester Massachusetts.” Ph.D. Thesis, Northwestern University, 1955.
13. A number of studies have noted social problems in the town. Several were pointed up by Andy Merton in his “Winchester as Our Town ’76: Trouble in ‘Paradise,’” Boston, August 1976, p. 55.
14. Interview of Edward F. O’Connell by Charlene Band, November 3, 2004.
15. Interview of Robert Gallant by Amanda Yost, March 22, 2003.
16. Envision Winchester was an effort coordinated with the Visioning and Strategic Planning Committee to gather community input for the development of a vision, goals, and objectives for a strategic plan for Winchester. The Strategic Plan was completed in 2004.
17. Jon Gorey, “Top spots to live in Greater Boston in 2018,” Globe Magazine, April 19, 2018.