Winchester was settled by farmers, colonists from Charlestown who wished to take advantage of the abundant waters and fertile fields of the area. The original land grants were recorded in 1638, but as parcels were bought and sold, inherited and divided, their boundaries were redefined. What emerged in the first two centuries was an area divided into farms of varying size, many of which were handed down through generations of the same families. Today only a remnant of the Locke Farm remains a working farm.

“There are piles and piles of hard cash in garden truck if it is only got to market on time,” a newspaper reporter stated in 1889. “Winchester does a good deal of it and might do a great deal more. No territory is better located for successful market gardening than Winchester.”1 

Locke FarmWinchester was indeed suited to farming. In 1873, an historian wrote, “It is a very pleasant town. The natural features are attractive and greatly embellished by cultivation. Its rounded hills afford many fine prospects; a beautiful stream of water, called the Aberjona River, passes through the midst of it.”2  (Pictured left is the George Locke farm on Ridge Street.)

By that time, the “pleasant town” was in transition from a land of farms to a suburb. From the latter part of the 19th century on, the farms were increasingly subdivided into housing lots for both professional men and laborers, though pockets of agricultural activity continued in Winchester into the twentieth century.

During the transition, “the town was a compact group of homes surrounded by farms that supplied the Boston market with produce. In those days the great farms of California, Texas, Florida, and Long Island did not exist and all the fresh summer vegetables were raised in Winchester, Arlington, Medford, and the towns further out on land now covered with houses.”3 

By 1930, the most extensive farms were on the western hills, Cambridge Street, and in the southeast and northeast sections of town. In 1950, most of the active farms bordered Cambridge and Ridge streets, and most of these disappeared during the post-World War II building boom. In the closing years of the 20th century, only two farms, one on Ridge Street and one on Cambridge Street, were left. One of those was sold for development in the 21st century, leaving only one working farm, a 20-acre remnant of the Locke family farm along Ridge Street. 

Richard IrwinThe type of farming practiced also evolved over the centuries. At first, farming began as a means of survival. When country stores began to appear, farmers engaged in bartering with the merchants. In the 19th century, subsistence farming gave way to market gardening and specialty crops, such as fruits and squash. Blue hubbard squash was a particular favorite of the Ridge Street farms. Horse-drawn wagons laden with vegetables for Boston often started at dusk to be at the market first thing in the morning. (Pictured is Richard Irwin on his way to market.)

Boys on Russell farmSome of the farm owners of the 19th and 20th centuries were descendants of the colonists. Others moved in from other towns or states and from Europe. The farmer was an important employer for itinerant and immigrant laborers, though day laborers increasingly went to the factories for better wages. A number of local youth also found work on the farms (such as the boys pictured on the Russell farm). The Yankee farmer was long an honored part of the town, taking part in town government and politics and getting involved in local projects, business, committees, and clubs. 

What follows is not a comprehensive history of farms but a look at a few prominent sites and some of the 18th- and 19th-century architectural remnants. This look is organized primarily by the early streets which were formed to connect the farms to the churches, mills, and markets.4 


212 MainToday the name of Symmes is preserved at the Symmes Rotary on Main Street where a few Symmes houses survive (including 212 Main St., pictured right) and where the family continued farming into the mid-20th century. Originally the family owned 300 acres, granted in 1638 to Zachariah Symmes. Though Rev. Symmes did not settle there, his descendants did. The Symmes farm changed over time as parcels were bought and sold, but portions were handed down through the family into the early twentieth century. [Read more: Symmes Farm]      

One major sale of Symmes land occurred in 1715 when William Symmes sold a large part of the land east of Main Street to Ebenezer Brooks. In his house was born one of the most distinguished residents of this area, John Brooks, governor from 1817 to 1823 (while that area of Winchester was still part of Medford). [Read more: Home of Governors]

The Symmes family used their property not only for farming but also for industry. Zachariah’s son Capt. William Symmes dammed the river (near where the parkway crosses it) and built a mill. William’s son William (1678-1764) bought out the other heirs, built a new mill, and carried on the business of fulling and dyeing cloth. Although it passed into the ownership of the Bacon family, the area remained industrial through the mid-20th century. 

Russell farmAnother prominent farming family, located between the Symmes farm and West Medford, was the Russell family. James W. Russell (1844-1925) farmed his own land as well as land on the Brooks estate.5  Working in the area from Grove Street to North and South Gateway over to Winford Way, he became a well-known market gardener, one of the largest celery growers in the state.6  

Former selectman Harry Chefalo recalled, “They grew a lot of celery. They used to build these big pits that were two hundred or three hundred feet long... every fall. They would take them down in the spring so they could use the land to grow more stuff. They used to put leaves on it to cover it. You could go in there and it would feel like there was heat in there. They used to put cabbage, celery, lettuce, very little, squash. … A truck would go into the market every day with a load of stuff.

“I used to go down after school and we would have to take the cabbage in out of the pits. We would bring it in the wash room and rip off the bad leaves and put it in good shape and then they would take it into the market. Celery you would do the same thing.” The boys were paid “sixty cents a day or something like that. It was good in those days. A dollar was worth something.”7 

86 MainRussell built his home on Main Street, now the Children’s Own School, 86 Main Street. A charter member of the Boston Market Gardeners, he served as one its presidents. His son James William grew up farming and took over the farm though his own home was on Wolcott Road. A graduate of Amherst College, Russell married Charlotte Skillings, granddaughter of David N. Skillings, one of the wealthiest residents of the town. He served on several Town committees, was a trustee and vice-president of Winchester Savings Bank, a Trustee of the Funds of Winchester Hospital, and a member of the Country Club.


West of the Symmes farm below Church Street lay another significant 1638 land grant, a 300-acre parcel granted to Increase Nowell, who did not settle on it. Richard Gardner purchased it in 1659, after which four more generations of Gardners farmed the land along Cambridge Street, south of Church Street, and up High Street. Cambridge Street was, in fact, known as Gardner’s Row in the early years.

103 CambridgeLike Symmes and Nowell, Gardner came to Massachusetts during the Great Puritan Migration. In 1648, six years after arriving in Woburn, he received a ten-acre grant of land called Round Meadow, located on the east side of Cambridge Street, west of Winter Pond. After buying the Nowell lot, he built a new house where today’s 103 Cambridge Street (pictured left) now stands.8  

Richard’s grandson John, having become a minister, sold 70 acres of Gardner land on the western hills to the Hutchinsons. However, the bulk of the farm remained intact through the fourth generation when four Gardner brothers (John, Edward, Henry, and Samuel) lived in four separate homes on Cambridge and High Streets. After the brothers’ deaths, more parcels were sold off until Gardners no longer lived in the town. 

GardnerSwanA second surviving Gardner house stands at 89 Cambridge Street. Edward Gardner’s son Edward sold that home to John Swan in 1818. Formerly the house had a wing devoted to making shoes, an occupation followed by many farmers. The shoe-shop wing was converted into a home and moved to 7 Gardner Place. The barn was also converted to a home at 2 Gardner Place. [Read more: Shoe-making]

The homes of Henry and Samuel Gardner were sold outside the family and are gone. Former governor Edward Everett bought the Samuel Gardner property (and other adjacent land) in 1858. Everett did not live in the Gardner house, which burned down, but rather built a mansion overlooking Mystic Lake where Robinson Park is now. 

The last Gardners to live on Gardner’s Row were sisters Sarah, Hannah, and Patience at the John Gardner house (#103), probably built on the foundation of Richard’s house. Abel Green farmed their land. According to the 1860 agricultural census, he had one horse, one cow, and one swine, and his produce included 50 bushels of Indian corn, 100 bushels of Irish potatoes, $50 orchard products, $125 market garden, and ten tons of hay. 

By the time of the Gardner sisters’ deaths, the land was more valuable for house lots than for farming. In 1872, Abijah Thompson bought the property in order to divide it and sell or mortgage lots. [Read more: The Gardner Farm]

Stephen Swan farmAnother old farm house, highly renovated, stands at the Winchester/ Arlington line. South of the Gardner farm, John Swan’s brother Stephen inherited a house with a farm from his father. At the beginning of the 20th century, instead of being subdivided for housing it was purchased by the Winchester Country Club for a golf course.9


195 CambridgeCambridge Street north of Church Street continued to be farmed after the Gardner farm was all broken up. Richard Gardner’s neighbors to the north, in what was Woburn before 1850, were the Johnson and Carter families, but it was a later family, the Wymans, who arrived in the 18th century and gave their name to that area, Wyman Plains (known after development as The Flats). Hezekiah Wyman, a legendary figure from the Revolutionary War, bought Richard Gardner’s Round Meadow land, and his descendants farmed there through the 1840s and were active in village affairs. Two of the Wyman houses passed into the possession of Lockes, members of a family which also farmed along Ridge Street. Pictured is a Wyman house (#195). Another thriving farm belonged to the Puringtons (#161). [Read more: The Purington Load] The land is now all divided into residential lots.

Pansy PatchThe last working farm on Cambridge Street was the Grover/Purcell farm. In 1884, Henry Grover (1838-1910), who had left farming in Vermont and worked in the wholesale grocery district in Boston for 20 years, bought 25 acres and replaced the existing house with a new one (#223-225), plus a barn, two hen houses, and two greenhouses. The Purcell family took over ownership of the buildings and a 9.3-acre parcel in 1923. The Purcells were still selling vegetables as well as flowers in the mid-20th century. During World War II, when awards were given at a Harvest Fair to encourage Victory Gardens, only three special awards were given in the commercial class, two to florists and one to John Purcell of Cambridge Street for his “splendid exhibit of vegetables.”10  In its last decades the farm was known as the Purcell Pansy Patch. It was sold in 2005 to a developer who moved the National Register house and built a cluster of townhouses next to it.


Mystic ConservatoriesIn the 19th century, some farmers specialized in garden plants. The corner of Bacon and Central streets was the location of the Mystic Conservatories. Florists located in other areas, notably Cambridge Street. At the intersection with Wildwood Street, Samuel Twombly, who had a thriving business in Boston, made his home. [Read more: Samuel Twombly]

Northwest of the intersection of Cambridge and Wildwood, at 178 Cambridge Street, was the Little Farm which became the Winchester Conservatories, a greenhouse for flowers. And the Purcells grew flowers.

Mahoney’s:  The best known garden center on Cambridge Street was run for decades by Paul Mahoney. His grandfather, Edward Russell, a market gardener, purchased a farm at 228 Cambridge Street (pictured left), including a house and 80 acres. He added more acreage until it reached 182 acres. After his death, hi228 Cambridges widow rented out the farm. At her death in 1946, Martha Russell Mahoney inherited the farm, including 53 acres on Cambridge Street. At age 11 Mahoney went to live at the Russell farm. “I always grew up with a little gardening and growing vegetables, and I liked to grow things. I started with the vegetables and put more and more into plants. I had at one time planned to become a lawyer and then I graduated in 1957 from Boston College. I went into the service and when I came out, I started doing a little part-time teaching for Boston schools and starting the business here selling vegetables and things. Then I decided to take a year off from teaching and give a go at this full time and never looked back.

“I took a shot at it in 1959 full time. I started selling off of a couple of saw horses and an old door. Bunches of rhubarb–three for a quarter.”11  Thus began Mahoney’s Rocky Ledge.

The fact that Cambridge Street had an agricultural history helped Mahoney expand his business. In 1962, the Zoning Board of Appeals denied Mahoney’s request to build a greenhouse on his Cambridge Street property, on the grounds that it violated the Zoning Bylaw (due to the property being in a residential district) and had the potential to increase traffic hazards. Mahoney’s sister Margaret argued his case before the Superior Court, which upheld the ZBA decision, and the Supreme Judicial Court, which overturned it. The Justice observed that the new greenhouse would not change the character of the neighborhood, since the area was already commercial with two conservatories, the Purcell Farm, and a blacksmith shop. In 1965 and 1971, Mahoney purchased adjoining properties, the latter including the Winchester Conservatories. With branches in other communities, Mahoney’s became one of the town’s important employers. 

On the land to the north of the garden center, the last active blacksmith shop in town was situated (now gone). [Read more: The Smithy on Cambridge Street]


The farms along Ridge Street, High Street, and Hutchinson Road, being remote from the commercial center, survived longer than farms in other areas of town. A 1906 map marked only about a dozen dwellings on the western hills, indicating that most of the area was farm land and woods. 

201 RidgeThe oldest house in town, at 201 Ridge Street, is the Johnson-Thompson house, built about 1750. The house was probably built by William Johnson, a prominent figure in the history of Woburn. In 1858, Timothy Thompson, married to Caroline Johnson, inherited the property.

Remembering his family farm on Ridge Street, Ralph Mead Thompson said, “In those days, early 1900s, we used to have two or three men on the place year round. Then we started hiring Italian women in the summertime. The Italian women, most of them lived in East Boston, would come on the electrics, get off at Forest Street in Arlington, up Massachusetts Avenue, walk from there, up to here. All the farms up here hired help. They would come in March and find out how many you wanted. You would hear them coming up the road singing away to beat the devil. They were out working in the field at 7:00. They worked until 6:00 at night. Then as the season went on you would see them going home with bundles of vegetables on top of their heads. They carried them on top of their heads. And singing going home. Just imagine it. The fare at that time was 5 cents from East Boston out to Forest Street. It cost them 10 cents a day on the electrics. We were paying them 90 cents a day.

“In the early 1900s, on Ridge Street, there were approximately 2,000 tons of vegetables taken into the Boston market per year. Today there isn't one pound that goes down the road.”12  

A fire in 1920 destroyed all the farm buildings but the house. But it was economics which ended the life of the farm. The last owner, Ralph Thompson, took the title in 1938 and in 1947 paid off the mortgage. In 1966, he was forced to sell off nearly all the land in order to pay the taxes when the Town changed to 100% valuation. The Town itself acquired part of the land to construct the Vinson-Owen Elementary School.

At the south end of Ridge Street was the old Hutchinson Farm, originally part of the Increase Nowell land grant and Richard Gardner farm, which the Hutchinsons acquired in the 18th century. By 1908, the Irwin family of Arlington had spread into Winchester and was farming on parcels abutting Hutchinson properties on one side and Locke land to the other.

Another farm just off Ridge Street, on High Street, was that owned by Thomas Vinson, father of the champion figure skater Maribel Vinson Owen. Although a lawyer by profession, he also had a market garden, and it was once young Maribel’s chore to sell strawberries at a road-side stand. [Read more: The Vinson Farm]

The Vinson home was originally built for Capt. Josiah Locke, and it is that family name, Locke, which is best known for farming in Winchester, since a remnant of the George Locke farm survives as the Wright-Locke Farm, owned by the Town and the Wright-Locke Farm Trust. [Read more: The Locke Farm]

Although the Town had purchased parcels of farm land for fields or buildings, its acquisition of the Locke Farm as a farm was a first for Winchester, though this was not the first time that buying a farm was proposed. [Read more: Poor Farm]


Converse markerThe original land grants in the section of Winchester which was formerly part of Woburn were not as large as the Symmes and Nowell grants. Ranging from 5 to 90 acres (mostly under 50 acres), they were therefore more numerous. First settler Edward Converse was one of the largest land owners, his land including 80 acres of what is now downtown Winchester. The site of Town Hall was said to have been part of his sheep pasture, the Common part of his corn field, and the hill where the Lincoln School is situated was his apple orchard. He also combined industry with farming, building the first grist mill next to the Aberjona River where his Mill Pond still survives.

Over the centuries, some Converse descendants remained in town, but with the advent of the 19th century came the introduction of the railroad which encouraged members of the Richardson and Thompson families to begin the industrial development which would eventually transform the old Converse farm area into Winchester Center. 


Another prominent family which received land grants in Waterfield was the Richardson family. From Colonial times through the nineteenth century, Richardsons farmed all along Washington Street, which was known as Richardson’s Row. 

Although many immigrants wanted to leave farming behind, some farmed in The Plains.13  George D. Nelson, a native of Ireland, for example, had a farm during the latter part of the 19th century on Cross Street near Holton’s Grove. Many Italian immigrants worked as laborers on the Symmes farms. One of the last Italian farmers was Emilio Luongo, who emigrated from Italy in 1912 and had a four-acre market garden on Cross Street. His brother Emedio was also a farmer.

Forest CrestThe history of one former farm on Forest Street is instructive about changing uses and economic survival. About 1850, Lyman Dike built a farm house at the Stoneham end of Forest Street (later numbered 257). In 1865, it was purchased by Joshua Orne, who was a shoe cutter, and the next owner (1889-1912) was a mason, demonstrating that tradesmen might supplement their income with farming (or vice versa). A new use for the farm was found in the latter half of the 20th century under the ownership of Howard and Elsa Wittet. They raised hens and sold eggs by cart to neighbors14 and ran the Forest Crest Farm School for preschoolers, stressing health, out of door play, and real farm living, plus an educational program. Eventually, however, after their deaths, the land was sold to a developer who demolished the house in 1996 to make way for the Keenan Drive development.  


Brackett and pens Highland Avenue was sparsely populated until the 20th century. A unique site in the 19th century was the Brackett property up on Highland Avenue, where Edward Brackett cultivated specialty fruits and later, as a member of the State Commissioners on Inland Fisheries, had special charge of stocking streams and ponds with game fish, much of which was supplied from a fish hatchery built near South Border Road. When his duties expanded to include game, he devoted about an acre and a half of his estate to raising Mongolian pheasants and also bred Belgian hares. (Brackett is pictured left with some of his animal pens.)


In addition to the vegetables and fruit grown in town, a number of farm animals were raised, including cows, swine, goats, and chickens. 

Starting in 1893, during the years that an Inspector of Cattle and Provisions and his successor, the Inspector of Animals, made annual reports on cattle, the number of cows in town generally ranged from 200 to 300 though the numbers were higher in 1893 (386) and 1894 (562).

In the early 20th century, Winchester had several dairies though milk was also supplied from nearby towns such as Woburn, Medford, and Stoneham. An Inspector of Milk made his first report in 1906, and milk charts giving bacteria counts later began to be published in the local paper. Local dairies listed in those charts included Strawberry Farm on Washington Street, the White Farm and Forest Farm on  Forest Street, Jared Thornton’s farm on Cambridge Street, Clarence M. Perkins on Cross Street, and John Quigley on Wendell Street. Most were not long-lived. 

CowsThe most successful dairy farm in the 20th century was the Symmes Farm Dairy. Samuel Stowell Symmes, who worked on his father’s 100-acre farm at Symmes Corner during his youth, created the dairy after the death of his father (Marshall) in 1911.15  In 1934, his son Russell Symmes took over and became the owner on his father’s death in 1946. His cows could be seen grazing on the hill below today’s Highland Avenue. He retained ownership until his retirement in the mid-1960s. According to Symmes family history, the farmland was then sold, with the dairy business going to the Ware Dairy. 

In January 1918, Milk Inspector Maurice Dineen won a distinction for Winchester dairies. Entering a contest held by the Dairy Bureau of the Massachusetts State Board of Agriculture, he collected samples from 11 local milk producers. All samples were judged for bacteria, milk solids, flavor and odor, acidity, and bottle and cap. Six awards were given to the municipalities having the best averages. Winchester was awarded second prize. “He has once for all put Winchester on the map in all things pertaining to milk,” the Board’s secretary declared in a statement likely never to be heard again.


1. “Winchester” column in Woburn Journal, Nov. 8, 1889.
2. John Adams Vinton, The Symmes Memorial, 1878, p. 155.
3. Robert E. Sanborn, “Recollections of Winchester, MA,” typescript, p. 3.
4. The earliest roads included Main, Washington, Forest, Cross, Pond, Grove, Bacon, Church, Cambridge, High, and Fruit (now Hutchinson).
5. The Brooks estate was in Medford, though some of their land lay in Winchester. Winchester’s Town Forest, in fact, was formerly Brooks land.
6. The Winchester Star, Dec. 25, 1925.
7. Interview of Harry Chefalo by Marilyn Preston, November 12, 1999.
 8. The house may have been built on the foundation of Richard Gardner’s house.
9. A natural feature of this site was a stream known as Squaw Sachem’s Brook which crossed the land while flowing down the hill. Stephen Swan recalled his father’s talking about friendly visits by Native Americans to the stream. George Cooke, “Our Aborigines,” The Winchester Record, Vol. I #4, p. 273.
10. The Winchester Star, Sept. 24, 1943.
11. Interview of Paul and Doris (Barbaro) Mahoney by Marilyn Preston, February 26, 2002.
12. Interview of Ralph Thompson by Florence Hritzay, May 1980.
13. For area names, see “From a Village to a Town.”
14. The Winchester Star, Dec. 15, 1994.
15. “Samuel Stowell Symmes, The Winchester Star, Oct. 1, 1946.