Old Streets in Brookline

by Daniel G. Lacy

Proceedings of the Brookline Historical Society.
March 19, 1950, pp 31-43.
(Brookline Public Library: [Brookline Room] 974.45 B77hn)

The subject matter of my paper today is “Old Streets of Brookline.”

It has been a most interesting research experience to delve into the early records to find that the original grants of land in the Hamlet of Muddy River were given for the asking and were commonly known as tenant grants. Most of the owners resided in the Town of Boston and rented their holdings in the Hamlet of Muddy River, then a part of the Town of Boston, to tenant farmers. The earliest record of holdings in the hamlet, as shown on the plan of Mr. Theodore Jones (1920) (Brookline Historical Society — 1923), reveals that approximately seventy-six grants of land were made over the entire area.

The earliest reference for providing access to the settlement of Muddy River was in August, 1633, when at a Court held in Boston, it was, and I quote, “agreed that there shall be a sufficient cart bridge over Muddy River.” This official record clearly indicates that there existed at that time a road in this section, and apparently difficulty was encountered in crossing the Muddy River. However, in 1635, I find that there was not a single designated road in the hamlet. There is no authentic date mentioned in the early records showing the layout of this road, which later became known as the old Sherburn Road, and it is really the first reference to a highway in this area.

In March 1634, a cart bridge was ordered constructed over Muddy River, to be paid for by Boston, Roxbury, Dorchester, Watertown, and Cambridge. This became a pivotal point of the future travel of the town and the surrounding area.

The date of the actual construction of this bridge does not readily appear in the records, but as one continues his research of the old roads, it is quite apparent that the Sherburn Road followed an old Indian Trail, coming out through Roxbury, continuing and crossing the cart bridge at Muddy River. It then followed along the lines of Walnut Street, a portion of Boylston Street, and still a longer portion of Heath Street, to what was then known as Newtowne. This road lay along the southerly slope of Fisher Hill. The depression between the northeasterly slope of Fisher Hill and Aspinwall Hill (later designation) formed the bed of the Village Brook beside which now run the tracks of the Boston & Albany circuit.

The earliest map of the Town of Brookline, incorporated in the year 1705, was drawn in 1728 and filed with the Town on May 13, 1728, to find the geographical center of the Town in order to locate the schoolhouse. This map shows only four roads in an area of approximately 4,568 acres of land, viz: Newtowne Road (Road to Watertown Mill — known to us today as Washington Street), Road to Cambridge (known in the present day as Harvard Street), Sherburn Road (now Walnut Street, a small portion of Boylston Street, and a longer portion Heath Street), and a dead end road, unnamed, leading from the Sherburn Road toward the south. Of these the Sherburn Road is generally considered to be the oldest.

The Sherburn Road was an important thoroughfare to bring citizens not only to the geographical center but to the social center of the Town, which we now know as the site of the First Parish Church on Walnut Street.

It may be of interest to note that the traffic in the early days from Boston going toward the west passed out through Newbury Street and Orange Street (a part of the present Washington Street in Boston), over Boston Neck (Washington Street near Dover Street) through Roxbury by a road then called “the Cambridge Road”, passing the First Church in Roxbury where the Apostle Eliot preached, to the present day Roxbury Crossing, thence along the highway now called Tremont Street and Huntington Avenue, up through what is now the village, and out Walnut Street and Heath Street, then together with a portion of Boylston Street forming the old Sherburn Road.

About 1640 a committee of the Town of Boston was instructed to lay out a highway from Muddy River to Cambridge, and this is the first direct official layout of any highway in the Muddy River settlement. An early statement in the records that the “Road to Cambridge”, so called, which perhaps represented the modern Harvard Street, was to be “blazoned” through trees, gives a vivid description of the woodland that covered the town. Until 1793, there was no comfortable road to the Colleges except this one over Boston Neck through Roxbury and over the Muddy River bridge through Brookline. The only other route from Boston to the Colleges was by ferry to Charlestowne and, thence, over Charlestowne Neck to Cambridge” was laid out by the early settlers between Corey Hill and Babcock Hill. As late as 1843 there were no crossroads, and there were only about fourteen houses on Harvard Street (Road to Cambridge) between Harvard Square and the Brighton line.

What is now Aspinwall Avenue was just a lane running off Harvard Street to reach the Aspinwall House and another house occupied by a family named Perry. It was known as Perry’s Lane. This lane led toward the marshes, and, it is thought, met the “Road to the Marshes” so called, which ran along the lines of our Sewall Avenue of today.

Harvard Street of today follows along practically the same lines as it did in 1844.

In 1657 a notice was given to both Watertown and Cambridge that they might “depute some to joyne with ours deputed to lay out a highway from Muddy River to Watertown Mill, the said road to be four rods (66 ft) in breadth and directed by marked trees.” This was a real highway, and what is today Washington Street in Brookline and its continuation through Brighton and Newton to the Watertown bridge at the falls. This became a very important road and was used by all those traveling east or west between Roxbury, Dorchester, or Boston and Watertown. This road was laid out by early settlers on the most available land between what was known as Aspinwall Hill and Corey Hill, and had a common starting place with the Old Sherburn Road and the Road to Cambridge at a point later known as Brookline Village.

Repeated references to the Punch Bowl Tavern, which was located near the junction of these roads have been found and, in fact these references actually termed Brookline Village, “Punch Bowl Village.”

Although there was no apparent public interest or need for speed regulations along the Watertown Road directed by marked trees and the problem of sidewalks and street watering bothered nobody, nevertheless the sponsors of good roads must have been an active force because in 1661 we read — “It is ordered yt ye surveyors att Muddy River shall forthwyth repayre ye highway to Watertown Mill which is defective.”

An old Indian trail, “Eliot’s Path to Waban,” was laid out in the year 1671. This trail ran between the old Sherburn Road and Waban, and that portion which ran from the old Sherburn Road to Heath Street is known today as Pound Lane and Reservoir Road. The other portion of the trail ran along much the same lines as the old Reservoir Road to the west of the present day pumping station in Chestnut Hill and continued through Newton.

In 1674, we note a road marked “Road to the Marshes,” previously mentioned, which followed along the lines of a portion of the Sewall Avenue of today. Sewall Avenue was constructed much later to give access to the property in that section.

In 1677 the “Road from, Roxbury to Newtowne” was laid out, and is known today as Newton Street. In the early records of the Town this road is referred to as the “country road that leadeth from Roxbury to Newtowne through Brookline along by Lt. Gardner’s house.”

In 1679 a lane, along the lines of our present day Warren Street, was laid out and known as Woodward’s Lane. This way certainly ran along the lines of an old Indian trail or else on the path followed by Mr. Goddard’s cows to a pasture located on what later became the Howe property on Warren Street. This brings to mind the remark frequently made by visitors to Boston and Brookline, at that time being a part of the Town of Boston, that it would appear that many of the roads had been constructed along the lines of the cow paths.

Returning to the south part of the town, I note Clyde Street as having been laid out in 1715, and according to the records in the Town Clerk’s office, it is the first officially laid out street of the town. Although existing in 1715, this way had no name applied to it until it was laid out as an old Town way in the Town Meeting of 1844.

In the south part of the town also was located a lane, laid out before 1745, designated as the “Upper Road to Dedham,” and is today known as South Street. In this area also is Cottage Street, one of the earlier roads, laid out as an old Town way in 1841, with its location definitely described as passing the site of Captain Cook’s cottage.

Before continuing further the discussion of the early roads Appearing in our town, it seems only fitting to mention the mode of transportation of that time, for the transportation afforded by the roads of the town, was the important factor in bringing the people closer together and enabling them to communicate with each other. Prior to 1755 a great deal of pride was manifested in many of the records due to the fact that it took only three weeks for a letter to reach Philadelphia from Boston. In that year great reforms accelerated the speed so. that only fifteen days were required. The first stagecoach line was advertised in the Boston Evening Post of July 6, 1772 an running from New York to Boston and scheduled to take Only thirteen days for the trip. The first scheduled stagecoach line was established in 1783, which succeeded and continued until. the days of the railroad.

In the year 1806 we come to one of the great road ventures–the construction of the Worcester Turnpike through Brookline with the proud public announcement that on its completion the turnpike would give the maximum speed in a minimum amount of time because it was laid out on simple mathematical principles that a straight line is the shortest distance between two points. The engineers, however, failed to pay any attention to grades and forgot to take into consideration the difficulty to be encountered by the travelers over the long hills as well as the great effort required of the horses pulling the stagecoaches up the hills and holding back the load, going down the hill.

I was very much intrigued during my research on the Worcester Turnpike to learn the derivation of the word “turnpike.” It is an old English word and is described by the late New England historian, J. S. Edmands, as a gate made of rods or pikes shaped in picket form. These gates were hung on hinges and barred the road until the traffic had paid the required toll. Actually the legal phrase in the early law always designated these roads as toll roads, but in common usage the roars became known as turnpikes.

However, the construction of the Worcester Turnpike seems not to have had too important effect upon the development of Brookline.

This road was not known by the name of Boylston Street until it was so named in 1841 in honor of the Boylston family, who lived opposite the present Reservoir site and was prominently identified with the Town’s early history, and, of course, so often referred to in medical history.

The line of the Worcester Turnpike crossed “New Lane” our present Cypress Street, which was laid out in 1720 “to enable the northend inhabitants of the town to go to the Meeting House.”

School Street, known as “Schoolhouse Lane,” was one of the earlier roadways of the town and built with the continuous “New Lane” or Cypress Street to make a highway to the center of the town.

These two roads, of course, also connected the three main thoroughfares of the Town: the Road to Cambridge, the Road. to Watertown, and the Worcester Turnpike.

Returning to the original layout of the Worcester Turnpike, we find that after it crossed “New Lane” or Cypress Street, the old Sherburn Road was then followed for a time until what was known as Ackers Corner was reached. This is the point where our Chestnut Hill avenue of today meets Boylston Street–Chestnut Hill Avenue having been staked out in the year 1796 and designated the “Country Road to Little Cambridge” and later known as “Brighton Street.” The Turnpike continued on downgrade until it came in sight of Richard’s. Tavern, another famous tavern of the early day. Richard’s Tavern was located at a point on Heath Street at Hammond Street, as we of today know the location. To the right of this tavern extended an old highway which existed long before 1700, running toward Watertown. The old highway, which was called “Cross Street” in old Brookline records, has been known as Hammond Street since 1855.

Although of great benefit to the traveling public, the Worcester Turnpike apparently did not prove profitable to its proprietors for in 1832 they petitioned that it be established as a public and common highway. Brookline objected to this proposed laying out because the town would be burdened with the expense of keeping the road in good repair, as well as making the repairs termed absolutely necessary at the time. However, it was then agreed that the Worcester Turnpike Corporation would pay $500 toward the repairs of the road, and Brookline no longer objected.

During the period 1833-1870 many changes were made in Brookline along the line of the Turnpike road, such as widenings, relocations, changes in grade and other improvements, but none changed essentially the original character of the road. Today, of course, the turnpike or Boylston Street is maintained as a State highway.

One cannot delve into these references to old Brookline without observing the high regard for the Town as a residential suburb of Boston. The early Boston merchants settled here first as summer residents and later as all year-round residents. We find this referred to by the late Edward W. Baker, who stated that Brookline was being settled as a residential area by wealthy Bostonians on account of the excellent roads and beautiful trees which lined the roads.

This brings to our attention the importance of the work of the Surveyors of Highways in the early days. The town wall divided into three districts and each surveyor was elected annually and was supreme in his district. For example, if he believed that, after spending the allotted amount of money, that excessively bad conditions existed in the roads, he did not wait until the next Town Meeting, but would make the repairs immediately and send the bill to the Town Treasurer, whose obligation it was to recommend the appropriation at the next Town Meeting. Frequent references are found to the taxpayer, who, with his yoke of oxen, paid his taxes each year by repairing roads as ordered by the Surveyor of Highways.

It is most interesting to note at this time that a comparison of the lines of the old roadways with the lines of the roadways of today would result in the finding that on many miles of our streets the lines are identical.

Returning to the discussion of Brookline becoming known as a residential area, we find that the early Bostonians were anxious to tell their Boston friends that one of the main reasons they liked to settle in Brookline was the numerous hills on which they could build their substantial houses — thereby enabling them to have a better view of the surrounding countryside.

Some years ago, I recall, while walking through the Italian Garden of the Larz Anderson Estate with Captain Anderson, that he stopped at a particular spot in the garden and told me that Mr. Weld, who was the original settler on this hill, would very often on a clear day sit there and look toward Boston Harbor to observe one of his many ships coming in from the East Indies.

In the year 1820 the Town proudly boasted that its population estimated around nine hundred inhabitants and, of these, fifty per cent lived above the Meeting House and fifty per cent below. The analysis of the population of the fifty per cent living above the Meeting House shows that the streets in the south part of the town dated back, as I mentioned heretofore, to very early days and were really as much used as the roads from Roxbury to Cambridge or Watertown because the center of activity of the residents of the town, social or otherwise, was at the geographic center of the Town.

The year 1822 appears to be the beginning of the end of Brookline being a one hundred per cent farming community and becoming the residential suburb as described above — as shown by the subdivisions of the land from that date. In addition to this change being observed in 1822, we also find that from time on the large holdings of the Sewall’s, Sharp’s, Davis’, and White’s began, to show subdivisions.

The opening of that part of the Mill Dam, which is now Brookline Avenue, in 1821 was repeatedly referred to as an excellent way for Bostonians to come to Brookline by a good road. However, at first, in spite of this fact, the Mill Dam built from Charles Street in Boston, across the bay and over Brookline marshes to Sewall’s point had little influence on the Town, for the toll of 6 1/4c hindered travel.

Research in connection with the Mill Dam reveals that in 1868 the Town of Brookline accepted so much of the Mill Dam as lay within the Town limits as a public street called Beacon Street (hereinafter to be discussed); the easterly fork, at what is now Kenmore Square (the river being the Town line), was later accepted as Brighton Avenue, now Commonwealth Avenue; and the westerly fork was designated Brookline Avenue.

In discussing the period 1820-1822 I want to call your attention to the map, which we have here today, which shows the roads and waterways in the Town of Brookline as of 1822. The information on this map was obtained through, a great deal of research dating back to the year 1635. Appropriately, this map is entitled “First 200 years of Ye Hamlet of Muddy River as part of Ye Towne of Boston, Massachusetts 1632, incorporated 1705.” I sincerely hope that it will be possible for everyone present here today to see it at the adjournment of the meeting.

Proceeding to the Town Meeting held in March, 1841, I note a vote to appoint a committee to name the streets and Avenues of the Town. The description and names of those at the time connected with the Worcester Turnpike are as follows:

Road from Roxbury to Brighton Washington Street
Washington Street to Mr. Fisher’s corner Cypress Street
Worcester Turnpike Boylston Street
From the Post Office by Dr. Pierce’s Church to
Boylston Street
Walnut Street
From the Worcester Turnpike or Boylston Street to
Mr. Heath’s to Newton Line
Walnut Street
Heath Street to Boylston Street by
Mr. Penniman’s
Pound Street

Records, as a result of a survey by E. F. Woodward in 1844 on order of the Town Authorities, give us the first definite locations and names of Brookline streets. The following roads in the Town of Brookline, as surveyed in 1844 by E. F. Woodward, were supported by the Town of Brookline as public streets:

Name Length (Rods)
Boylston Street 855
Heath Street 612
Penniman’s Lane (Pound Lane) 67
Walnut Street 307
Warren Street 379
Cottage Street 112
Clyde Street 290
Newton Street 649
South Street 275
Brighton Street (Chestnut Hill Avenue) 242
Washington Street 528
Harvard Street 428
School Street 56
Cypress Street (New Lane) 150
Cross Street (Hammond Street)
(Newton Line to Heath Street)

The area of the town in 1844 was approximately 4,695 acres, as surveyed by John Kingsbury, Jr.

On Mr. Woodward’s map of 1844 we note smaller roads running off the Road to Cambridge, apparently not accepted as public ways at that time.

Washington Place which is now Davis Avenue was built and traversable as far as the Jones Farm or what is known as Emerson Street today.

Harrison Place, one of the early roadways of the Town, is now Kent Street, and was built from Washington Street to a point where it adjoins Station Street. This was originally nothing but a cart road, leading across the Davis Farm by the old house and barn. It was named in the year 1840 in honor of President Harrison.

What is now Linden Place was formerly an extensive cherry and apple orchard on property of Davis and in 1843 was laid out in lots and sold at public auction. Linden Place is referred to again along with Harvard Place, Vernon Place, as well as Pearl Place, in the report of the Committee on Beacon Street, dated February 25, 1853, when the committee recommended that the Town require streets to be of a certain width before accepting them as public streets. The aforementioned streets were referred to as being the beginning of the establishment of streets of this type, which because of the narrowness, would probably require large expenditures of the town in the future.

Andem Place was not opened until ten years later and was named, for Moses Andem.

In 1844 there was not a lane in all Longwood known as a public highway, As a matter of fact, the only public ways made in the Longwood area originally were Beacon Street in 1851, Longwood Avenue in 1857, and part of St. Paul Street in 1873. All other streets in the Longwood area, to the number of about twenty-five, were constructed at private expense.

In passing it is interesting to note, in this area, that when Commonwealth Avenue was built the fill had to be brought from fifteen to twenty miles away in the country, and it cost about forty cents per square foot.

In 1849 after a protracted discussion in Town Meeting, it was by a large majority voted to appoint a committee to oppose the construction of a public road from the northern end of the old Mill Dam, which would be Kenmore Square today, westerly through this Town to the Brighton Line. However, this proposed plan was successful, which brings us to the original layout of Beacon Street, a great event in the history of the Town.

In a report made by the Committee appointed to build the road, it was stated that the Committee believed this road to be the only one which had ever been laid out fifty feet wide and built at the expense of the Town. The farsightedness of this Committee is evidenced by its statement that all streets destined as great thoroughfares should be laid out fifty feet wide and no street laid out less than forty feet wide should be accepted by the Town. The section of this road west of Washington Street laid out in 1850 and the connection with the Mill Dam in 1851 formed Beacon Street.

Any reference to Brookline roads would be incomplete if mention were not made of the terrific upset caused by private promoters in 1886 when it was attempted to revamp and make Beacon Street into a parkway road 160 to 180 feet in width. The final report, in which the Town agreed to accept $150,000 from the proponents of this new boulevard plan and to contribute $465,000 as its share, brought forth the comment in the local newspapers that our Town would hereafter be as much benefited by this wide roadway as the promoters will be in that it would have a fine wide street for the development of the adjacent land for new types of homes etc. The leading promoter in this movement was Mr. Henry M. Whitney. As a result of this action we have the Beacon Street of today.

Electricity was then known to have been used as the power for propelling street cars and promoters of the enterprise promised electric cars on the new Beacon Street boulevard. Thus, after repeated and costly experiments, the first successful electric street railway in the world, on a through way, was provided on our own Beacon Street.

In the early 1870’s a committee was appointed to consider the methods and type of construction which the Town should adopt in the maintenance of its roadways. Correspondence was had with various committees in England and Scotland, and it was found that progress was being made in England on the type of road originated by an Englishman by the name of Telford. This type of roadway meant taking quarry stone and laying it pointed upwards and then placing gravel in the interstices on the surface. The stones were not tightly put together. Drainage was furnished by the interstices.

This method was expensive, and further experiments were carried on by a Scotchman by the name of Macadam where quarry stone was crushed in an improvised stone crusher and spread on the roadway six inches thick with gravel, thoroughly rolled in, on top. Water was then applied; the result being the type of road known as Macadam.

As a result of that committee’s report, the Selectmen appointed Mr. Michael Driscoll to serve as Superintendent of Streets in April, 1876, and he served in this capacity until 1925. It was in Mr. Driscoll’s administration that the Town first constructed its roads under modern methods. Mr. Driscoll’s reputation for good roads was heralded not only throughout the state, but by far distant communities throughout the country, who patterned their work from the method by which Mr. Driscoll built the fine roads of Brookline, which today are a proud heritage of the Town.

In closing my talk today on the “Old Streets in Brookline” which was intended only to acquaint us here with the history and origin of some of the early roadways of the Town, I think it would perhaps be best to summarize my topic by stating that from the very early days the roads of Brookline have been of utmost importance to the Town. Provisions have always been a certain pride in our roads dating back to the early days even prior to the date of the Town’s incorporation and has continued to the present day.

Resume – 1950

Number of miles of public streets, in the Town of Brookline — 90
Population of the Town of Brookline — 60,000 inhabitants-estimated.
Volume of traffic through Coolidge Corner in a twenty-four period — 48,000 vehicles.


As of December 31, 1949 there were 107 miles of public sewers In the Town of Brookline.

The brook running past the Brookline Railroad Station and across, the Mill Dam Road was laid out by the Selectmen as a common sewer on July 12, 1867. The location, according to a plan by J. Herbert Shedd, was approved by the Selectmen July 29, 1867. This action was approved by the special Town Meeting held September 13, 1867.

A public main sewer from Washington Street to the Charles River, was approved, by a special Town Meeting January 21, 1877 and provision made for construction of same.

On April 4, 1881, the Town Meeting authorized the Selectmen to lay out and construct lateral sewers.


Chapter 99 of the Acts of 1887 (Commonwealth of Massachusetts) authorized the Town of Brookline to provide for Surface Water Drainage.

The construction of Village Brook in 1893-1894 is the first direct reference to surface water drain construction in Brookline except the mention of catch basins draining into Sargent Pond.


There are approximately 14,000 roadside trees In the Town of Brookline, which include the following:

English Elms White Mulberry Flowering Cherry
Elm (White
or American)
Liquidambar Hickory
Red Oak Mockernut or Shagbark
Chinese Elms Pin Oak Horse Chestnut
Norway Maple Scarlet Oak Walnut
Sugar Maple White Oak Beach
Red Maple Black Oak Red Ash
Sycamore Maple Swamp Oak White Ash
White or Silver Maple White Pine Mountain Ash
Lindens (American-
Honey Locust Norway Spruce
Red Cedar Tulip Tree
Plane or Sycamore Tupelo Ginkgo
Willows, all species Sweet Gum Lombardy Poplar
Locust Carolina Cottonwood Flowering Crab
Catalpa Ohio Buckeye