Brookline Preservation Commission The Pill Hill Local Historic District: The Story of a Neighborhood Preface



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The Philbricks and Abolition

The Rockport granite Tappan-Philbrick House (1824-25), at 182 Walnut, was built by Joseph Sewall’s partner, John Tappan. It was said to be the hundredth house built in Brookline. Tappan’s brother Lewis, who married into the Aspinwall family, built a similar stone house in Brookline at about this time. The estate as John Tappan bought it was 18 acres — half being a “grove of oaks and hickories” in which he built his “mansion . . . of split blue granite, unhammered.” Apparently the open top of the hill seemed less desirable.

Tappan’s journals suggest he was largely responsible for designing the house, which he intended as a summer residence. He felt his children’s “physical and moral health” would be enhanced by “bringing them up in the country.” Before his new house was finished he demolished and subdivided his Boston estate on Federal St. and moved to Brookline — noting that he intended riding by horse the five miles “into town every pleasant day at an early hour and returning to dinner at 2 o’clock.” It was not to be.
His affairs were caught up in the depression of 1826. He had to sell the house and move to New York City, following his brother Lewis, a silk merchant, who eventually made him a partner. Later John reportedly built New York’s first granite-fronted commercial building. Like his better-known brothers Arthur and Lewis, John was an early abolitionist. (Lewis was largely responsible for obtaining the freedom of the crew of the Amistad.) Another bother, Benjamin, became a US Senator from Ohio and Tappan Sq. in the center of Oberlin is named after him. John and Lewis were also early members of the American Peace Society, which arose in the aftermath of the Napoleonic Wars and survived until the Civil War.

The Tappan-Philbrick house in the mid-nineteenth century with cows in the yard.
In 1828 John Tappan sold the estate for about $14,000 to merchant William Ropes, who sold it to Samuel Philbrick in 1829. In later years wood framed clapboarded wings were added to the right and rear. At its largest, the Philbrick Estate included everything on both sides of Walnut between Irving and Walnut Place, as well as half of the old Lincoln School site and all of what is now Maple St. and Upland Rd. above Irving.

Samuel Philbrick, a birthright Quaker, and his wife were among Brookline’s leading and earliest abolitionists and a financial backer of William Lloyd Garrison’s The Liberator. The Grimke sisters, the Quaker-convert daughters of a South Carolina slave holding family, who were part of the more radical women’s-rights branch of the abolition movement, stayed in the house during the winter of 1836-37. One of Brookline’s first anti-slavery meetings was held there at that time — when a public hall probably could not have been obtained for such a meeting. It was a ladies-only event, but reportedly the poet and ardent abolitionist John Greenleaf Whittier listened from inside a closet. At about this time the Philbricks, at the suggestion of Wendell Philips, took a young black girl into their house as a domestic. They brought her with them to Sunday service at First Parish and had her sit in their pew, rather than in the balcony with the other black servants. As a result they were snubbed, they withdrew from the parish, and eventually helped establish Pill Hill’s Swedenborgian Church. The Tappan-Philbrick house is recognized as a part of the Underground Railroad, although its role in the abolitionist cause was far more longstanding and significant than its connection with the escape of two famous fugitive slaves (William and Ellen Crafts) would suggest.

Samuel Philbrick, one of Brookline’s leading and earliest abolitionists, and a financial backer of William Lloyd Garrison’s The Liberator.
Edward Southwick Philbrick, Samuel’s son, graduated Harvard in 1846 and became a civil engineer, working on such projects as the Hoosac Tunnel through the Berkshires (The Big Dig of its day, linking Boston and eastern Massachusetts with Albany and the West), and on the foundation designs of the Boston Public Library and Trinity Church. Later he became an expert in water supply (designing Brookline’s first system) and sanitary engineering, and a member of the MIT Corporation. His, in at least one instance, architecture-partner, William Ware, was MIT’s first professor of architecture. Philbrick was also briefly a Brookline Selectman and provided expert testimony at the inquiry into the Great Boston Fire of 1872.
A mid-nineteenth century advertisement extolling the “rapid transit” to “the West” made possible by the Hoosac Tunnel through the Berkshires, which Edward Philbrick worked on as a young engineer.

An active abolitionist like his father, Edward Philbrick lead a venture which purchased one third of Union occupied St. Helena Island S.C. in 1863 and set out to develop the “Free Labor Cotton Company” which hired freedmen to operate thirteen plantations. After the war, the land was divided and sold mostly to freedmen at below market rates. The “Philbrick Experiment,” as it is now called, showed that southern freedmen could be integrated into the free labor market and then it allowed them to buy farms totaling over 4,000 acres — something local white landowners would not have allowed at any price. However, it should be noted that many of the 70 investors were cotton mill owner or cotton brokers. One of the ironies of New England’s support of abolition is that the insatiable demand of its cotton mills sustained the institution of slavery in the decades before the Civil War. It should also be noted that Philbrick’s “experiment” netted his backers a handsome $80,000 — something like a 60% return on their investment — probably due in no small part to the low price originally paid for the land.

Samuel had died in 1859. (His grave is under a slab in the Old Burying Ground.) Edward inherited the estate and began to develop it. He and then his heirs, who later commissioned a subdivision plan from Fredrick Law Olmsted, Sr. in 1889, became one of Pill Hill’s two primary developers, having laid out the upper portion of Upland Rd. and Maple St., building at least ten houses on those streets and Walnut St., and platting at least thirty building lots, in addition to the family’s role in the design and construction of the Swedenborgian church. Edward Philbrick’s widow died, aged 88, in 1922, leaving the house and grounds to Harvard, which promptly sold it for $16,000. One subsequent owner was the Rt. Rev. Anson Phelps Stokes Jr., Episcopal Bishop of Massachusetts. The estate is now protected against sub-division and further development by a preservation easement, generously granted by its present owner.
The puddingstone, mansard-roofed, Edward Philbrick House, just to the west at 24 Walnut Place (1857), was possibly built as a wedding present for him and remained part of the estate throughout the Philbrick’s tenure. After World War I it doubled briefly as a convalescent home for service men. It was modified in 1939 by the removal of its gambrel roofed front wing, after there had been an initial application for demolition of the whole house. The timing suggests it may have been damaged in the great hurricane of 1938.

For over a century this house had a Walnut St. address — and for much of that time a long driveway paralleling Walnut Place, just a few feet away, all the way down to Walnut St. Finally in the 1980s the 160-year old estate boundary was breached and this house gained a more convenient Walnut Place entrance and address — and a lot for the new house at 10 Walnut Place was made possible.



The Edward Philbrick House in 1919 with two servicemen convalescing in the fresh air on cots and another in the background near the house. At that time the house, then still part of the Philbrick Estate, was occupied by the Philbricks’ Winsor in-laws, possibly shown here. The entire front wing of the house, to the right, with its distinctive cloche-like gambrel roof, and the central third-floor mansard tower, were eliminated in the 1939 renovation.
Philbrick’s developments began along the north side of Walnut and encompassed almost all the properties in view from the front windows of his own house. From east to west, the first was a double house at 167-169 Walnut, designed by Cabot & Chandler. Helen Hopekirk a Scottish-born virtuoso pianist and composer, whose performances contemporaries compared to Clara Schumann’s, lived at 169 Walnut and taught at the New England Conservatory after she decided to settle permanently in the Boston area in 1897.


There are Philbrick double houses at 173-175 Walnut and 187-189 Walnut (1869) — with the latter being a very large double Mansard. Phillips Ward Page an aeronautical pioneer lived at 173 Walnut. He received his pilot’s license in 1911, became a flight instructor for the Burgess Aeroplane Co. in Marblehead, the aviation editor of the Boston Herald, and took the first moving pictures of Boston from the air. He died in 1917, aged 32, when his navy seaplane crashed in the English Channel.



Helen Hopekirk, Scottish-born virtuoso pianist and composer, lived at 169 Walnut St. Later she moved to 31 Allerton.

In the middle of these substantial twin houses, and then also part of the Philbrick estate, is the modest 1840s house at 181 Walnut. A longstanding neighborhood myth, apparently unsupported by evidence, had this house linked to the Tappan-Philbrick house by a tunnel — a literal-minded embodiment of the Underground Railroad. Next to this house is Walnut Path, originally Cat Alley. Acquired by the Town from the Philbrick estate in 1890 and widened, it is probably the oldest of Brookline’s unusual set of pedestrian paths.

195 Walnut (ca. 1870) was the first Pill Hill home of Charles Ware, who during the Civil War contributed to the publication of Slave Songs of the United States. He later moved to 52 Allerton. This house was later occupied by Mr. & Mrs. Henry Curtis Snow. She was the sister of Mrs. Arthur D. Little, at 107 Upland. 205 Walnut, (1860s) had a second story added in 1890 by Philbrick’s brother-in-law, Alfred Winsor, who was president of the Boston Towboat Company and other steamship lines. When women’s suffrage was being debated during and after World War I, it was occupied by Henry Preston White, a landscape architect, and his wife Sara C. White. She was deeply involved in many reform and welfare organizations, including organizing a “model moving picture show” under the auspices of the Brookline Friendly Society. But, like some other neighborhood women, she was also an active anti-suffragist.
Phillips Ward Page at the controls of a Burgess Aeroplane. He lived at 173 Walnut St.
While much of Pill Hill was the creation of the Philbrick Estate and the Brookline Land Company, Walnut St. was there first and it is reasonable to consider the remainder of it before turning to those two developments.

Walnut Place

Walnut Place, immediately west of the Philbrick Estate, feels like a quiet county lane and uniquely gives a sense of what much of mid-nineteenth century Brookline was like. (The lower straight section on the Guild Estate was originally Guild St. while the curving upper portion on the Williams Estate was Green Bank Ave.) The much modified, brick 35 Walnut Place (1889) was designed by William Ralph Emerson for Moses Williams’ son Charles. The Italianate 56 Walnut Place (1868) was the home of the three Stevenson sisters, one of whom was a Civil War nurse. They later moved to the abutting 94 Upland. The Greek Revival 67 Walnut Place (1849) was Moses B. Williams’ home and 61 Walnut Place (c. 1860), now a home, was his barn. 67 Walnut Place recently acquired a porch with massive Greek Doric columns — archaeologically “correct” yet playfully disproportionate to the house. 76 Walnut Place (ca. 1865) a slightly larger than life Mansard “cottage, was the home of Cyrus M Warren, part of a remarkable family that gained control of the “worthless” coal tar byproduct of the production of illuminating gas and proceeded to develop asphalt paving, tar paper, flat gravel roofs, and kerosene refining. His brother Samuel was minister of the Swedenborg church on High St. from 1864 to 1868 and operated a private chemical laboratory researching aniline dies and other hydrocarbon derivatives.

An almost empty Pill Hill in 1855. The plateau-like feature in the center is Pill Hill with Walnut Place crossing it — not an accurate rendering. The hill extends much further southeast ending as the peninsular Edgehill Rd. Only the Tappan-Philbrick House and two now-lost Wright houses then occupied the area now bounded by Walnut St., Walnut Place, and High St. (What looks like the beginning of High is Village Lane.) The then-new railroad (now the Green Line) can be seen paralleling the Town Brook, just above the Worcester Pike (Route 9) — and Brookline Village is beginning to take shape along Harvard St. beyond it.

At the far end of Walnut Place are two simple houses built in succession for himself by Amos Atkinson, a Boston merchant who wanted to “rusticate” in this hidden corner of Brookline: 100 Walnut Place (1842) and 94 Walnut Place (1851). His son Edward was a boyhood and college friend of Edward Philbrick’s. Upon marrying Edward moved just past the Brookline Reservoir to his wife’s family’s estate on Heath Hill but maintained close Pill Hill connections. Along with Philbrick’s brother-in-law, Alfred Winsor, he was a director of the West End Street Railway Company, which developed Beacon St. He was a prolific writer, the inventor of the “Aladdin Oven”, and an ardent abolitionist who helped finance John Brown’s raid on Harper’s Ferry and sheltered John Brown’s son when he arrived in Brookline, armed to the teeth, after it failed. He was also a member, along with several Pill Hill residents, of the Anti-Imperialist League. Edward Atkinson, in the role of pater familias is portrayed in The Big House: A Century of Life in an American Summer Home, the story of a larger than life summer house on Wing’s Neck, Cape Cod, and of the Brookline family that belonged to it.



Walnut Street

The cluster of innovative early 1950s modern houses at the bottom of Walnut place, 210, 220, 224, & 230 Walnut, occupy the sites of the two houses on the Searle Estate demolished after the Great Depression. Granite gateposts on Walnut Place once lead to the smaller Searle house, while the other was reached by the present common drive serving most of the houses. 220 Walnut, a “duplex,” and 230 Walnut were built by Richard H. French and Roberta Kohlberg French, who probably was the designer. Both were MIT graduates. He was a hydrologist. She had written a 120-page Bachelor of Science thesis on flat roofed buildings in New England. 230 Walnut has two newer “tower” additions. 210 is by David Abrahams and 224 by the Core House Corporation whose architect, Edward A Cuetara, was an associate of the Architect’s Collaborative. 230 and 210 were owned by two brothers, both doctors. These innovative houses are a positive reminder of how egalitarian and idealistic America was after having experienced the Great Depression, the New Deal, and the social leveling of WWII and the GI Bill. 222 Walnut is an Acorn house from the 1980s.

Walnut St. looking west in 1876. On the left is the stone retaining wall of the Philbrick Estate without the present wood fence on it, which was added by the Burrages in the 1930s. At the end of the wall is Walnut Place with the now subdivided Searle Estate beyond it. On the right are a group of oaks, the last of which survived into the 1980s when it succumbed to old age and root damage caused by street paving. At that time the town had wanted to cut the tree and straighten the street. The neighborhood disagreed. The sidewalk is still wider there.

Opposite them is an earlier sort of modernism. The highly romantic, Arts and Crafts house at 217 Walnut (1908), with its glacial-bolder masonry and lych gate at the sidewalk, was designed by Henry F. Keyes for B. Frank Carroll, a builder. Its red tile roof suggests an affinity with the California Mission Style. While advertising its owner’s craft it was also featured in an advertisement for Thomas Edison’s new portland cement stucco — which was applied over walls made of structural hollow clay tiles, one of many innovations of that inventive period in construction technology. Immediately to its west are two of the neighborhood’s older houses, 233 Walnut (ca. 1843) and 239 Walnut (1836, with later additions). Opposite the latter and occupying the former Cobb Estate are Oakland Rd. and the Puddingstone Rows (1886), at 234-258 Walnut, two magnificent sets of Romanesque stone townhouses built for Albert A. Cobb, a prominent Boston East Indies merchant, by his son Henry Ives Cobb, an important Chicago architect, whose best known works there include the English Collegiate-Gothic core of the University of Chicago. (Recently, after 125 years, a set of the original working drawings for the east row was found in one of its attics.) Before Oakland Rd. was cut through, the Puddingstone Rows were fronted by a sweeping drive, called Walnut Terrace, within a unified Frederick Law Olmsted landscape.

The Olmsted archives contain this beautiful unrealized plan for developing the rest of the Cobb estate, which was behind the Puddingstone Rows (what is now Oakland Rd.), with an additional 36 row houses, presumably also by Albert Cobb’s son, Henry Ives Cobb. Walnut St. is at the left edge with the two Puddingstone Rows facing Walnut Terrace, their original curved private drive. (“Terrace” is a British term for a unified set of row houses.) Sited between them is the 1829 Cobb house, now moved back and turned at 22 Oakland Rd., but then still on its original site. The three proposed new row house terraces are arrayed around a “green,”— a more refined version the one Olmsted created, in a rather ad hoc manner, at about that same time, on the Philbrick Estate (now Philbrick Green on Upland Rd.) The south end of the Cobb Estate was bounded (behind the shortest of the three proposed rows) by the north side of what was then called Sewall Pl. (Now Rice St.). The area proposed for the 36 new row houses now contains approximately ten two- and three-deckers and ten single-family houses.

Through the early years of the twentieth century, 256 Walnut was the Chilean consulate and home of the Chilean Consul, Horace N Fisher. He had been a staff Lt. Colonel in the Civil War at the Battle of Shiloh and at Chickamauga, where he was wounded. Later, he found himself in the middle of the War of the Pacific between Chile, Bolivia, and Peru. He wrote extensively on matters of military history and, contra others on the Hill, strongly advocated annexing Cuba, the Philippines, and Puerto Rico after the Spanish American War — to the point of even writing a book on colonial administration.
The Cobb family lived in an 1829 farmhouse, which stood facing Walnut St. between, and back from, the Puddingstone Rows. The Cobb house and its carriage house, now a residence, were moved in 1903 to what became 22 Oakland Rd. Recently it was restored with the removal of artificial siding. Opposite 22 Oakland is Vogel Terrace, four once-identical houses around a cul-de-sac. Built in 1910 for rental purposes, they were designed for Emily Vogel by Funk & Wilcox, the architects of the fire station at the bottom of High St. 19 Oakland (1909), by Everett & Mead, at first seems an early nineteenth century Greek Revival house. Only the cozy little porch, with its built-in benches, typical of the early twentieth century Arts & Crafts era, betrays its true date. The more typical Arts and Crafts House at 15 Oakland has a similar porch. The houses at 28 & 32 Oakland were built in 1907-08 and show the influence of the Shingle Style in their gambrel roofs and shed dormers, with Colonial detailing at the front porch.

The five substantial triple-deckers (ca. 1910-14) opposite the Puddingstone Rows were built on the relatively modest estate of the Winsor family, whose daughter had married Edward Philbrick 50 years earlier. 255 Walnut is particularly handsome with considerable fine Colonial Revival detail. It was designed in 1910 by James J. Rantin, an Irish-immigrant architect, who was particularly prolific in this type of housing. Tucked unexpectedly behind 247 Walnut is the Winsor’s 1840s Greek Revival house with its Doric columned porch.

Just beyond them are three solid, Rationalist, almost machine-like, examples of the Stick Style. 267 Walnut (ca. 1878) was built for Anna Jones, a member of the Swedenborgian Church on High St. Sadly neglected and asphalt-sided when the Historic District was created, it has since been restored. Noah S. Jenney, treasurer of Jenney Oil, built 273 Walnut (1879). At the time Jenney’s son, Alexander, lived at home and attended the Architectural Program at MIT. After graduation he worked for H.H. Richardson, whose office was in Brookline. Alexander may have designed his father’s house. As it happens, the pioneering Chicago skyscraper architect William LeBaron Jenney, a relative, was then also building houses there in a very similar style — no connection is known. Its matching carriage house-like garage/studio dates from 1997. 287 Walnut (ca. 1880), at the corner of Cypress, is another good example of this type. It was designed by Abel C. Martin, a talented young architect who died in an accident the year after it was built. Before World War I it was the home of landscape architect and city planner George Gibbs who worked for the Olmsted practice, both here and in California. The last house in the district is 156-158 Cypress (1886) an unusual for Brookline, double brick house with porch. Its decorative brickwork is reminiscent of the Panel Brick style commercial blocks and apartment houses in Brookline Village.

On the south side of Walnut St., which had begun to develop a decade earlier than the north side, is a late Italianate house (1879) at 268 Walnut and Mansard houses at 276-278 Walnut (1876), 262 Walnut (ca. 1863), and 284 Walnut (1863), the last of which a few years ago had its long lost, late nineteenth century, porch restored and some jarring, steel framed, 1950s picture windows removed.

Returning to the east of the Philbrick Estate on Walnut there are: a simple house built in 1844 for Charles Foster, a boot and shoe dealer, at 163 Walnut; an unusual house at 141 Walnut (ca. 1845-55) with an L-shaped two story colonnade (the second floor veranda came later); an Italianate houses at 157 Walnut (1851-52), built by Abraham Lambert, a blacksmith; and 149 Walnut (1858). The central unit of the three Gothic-gabled brick rowhouses at 129-137 Walnut (1877-78) is officially a church. Its neon sign was stolen years ago and the Preservation Commission supported its replacement as part of the neighborhood’s character.


At the edge of Brookline Village
A postcard view of the fire station at the foot of High St. in 1912, with a trolley shelter in the middle of the street. The large building to the left of the fire station was the Brookline Friendly Society’s Union Building, a settlement house, on the site now occupied by the high-rise. Single-story “taxpayer” shops are also visible to the left of the fire station, where there is now a parking lot. Beyond the fire station, down Route 9 where the Dunkin Donuts is now, was Mr. Quinlan’s carriage works. Yet, even then, the Wright Estate which abutted the two apartment hotels at the corner of High and Walnut, still remained undeveloped. At that time Pill Hill was even more abruptly contiguous with the urbanity of Brookline Village than it is today.
In the mid-nineteenth century, three major events led to growth in Pill Hill. The Town’s civic center shifted from the area around First Parish to Brookline Village. The Brookline Branch of the Boston & Worcester Railroad (now the Green Line) came to the Village, providing a more direct, reliable commute to Boston. And in 1844 the boundary between Brookline and Roxbury was moved from near High St. to the Muddy River. This annexation resulted from a petition of 107 residents of the “Farm” area near Washington St., where the Brook House is now — an area then part of Roxbury. In the late twentieth century a few older Pill Hill residents recalled an earlier time when students living in the annexed area reportedly still had preferential enrollment access to Roxbury Latin, despite their Brookline addresses.

At 72 Walnut St. (1875) is the Victorian Gothic former Hotel Kempsford, an early apartment hotel with duplex units. The parlor and dining room of each apartment are on its lower floor, with the bedrooms above connected by a private staircase. Next door, at 64 Walnut/13-21 High, was the Hotel Adelaide. These two buildings, both now condominiums, were designed by Obed F. Smith. Together with the fire station, they are almost all that survives south of Route 9 of Brookline Village’s original urban fabric, which once stretched seamlessly from here to Harvard Sq. beyond the railroad tracks. All of Brookline Village that flanked both sides Route 9 from High St. to the Boston line was swept away by the 1960s urban renewal of the “Farm” and “Marsh” areas, which were replaced by the Brook House and Brookline Place projects respectively.

Brookline’s town seal, adopted in 1848, shows a train crossing (on a trestle) the seemingly-open waters of the then still unfilled Back Bay, towards an agrarian Brookline wreathed in blooming roses — with the Hub of the Universe rising from the waters in the distance. Both the inclusion of the unusual historical “explanation” around the top and the central vignette (probably inspired by an 1839 engraving with a similar composition of a train approaching Boston), closely identify Brookline with Boston. But all the symbolism asserts that Brookline was not just suburban but prosperously agrarian — a suitable home, perhaps, for the country gentleman. A report explaining the design noted Brookline was formerly called “Boston Plantation” and “Boston Cornfield.” The seal was designed and engraved on a stamping die by Francis N. Mitchell for Fifty-six dollars.
When trolleys ran down Boylston, Harvard, and Washington Streets, their intersection here was a major junction and transfer point with shelters, like those in Coolidge Corner, in the middle of the Washington St. opposite the fire station. One other survivor of the Farm area is the “The Guild,” a 1903 apartment building at 36 High built with a communal dining room for occupancy by single men. It is the last building within the Historic District on the east side of High, and is set at a slight angle to High — facing instead the remaining short stub of Village Lane, which is almost all that remains of the old pre-urban renewal street pattern of the Farm. Significantly, Village Lane also demarked a portion of the pre-1844 Brookline-Roxbury town line. The house at 44 High (1882) was built for George Ropes a coal dealer.




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