It is not surprising that subdivision of the Philbrick Estate, beginning in 1876, started from the church with which the Philbricks were so identified. At first, Walley Ave., as Philbrick called the portion of Upland Rd. above Irving, only went around the east side and top of what later became the Green. Walley Avenue’s namesake is not clear. Possibly it relates in some manner to Sally Walley Phillips, mother of Wendell Phillips, the great abolitionist orator with whom Philbrick was associated. Its name was later changed by the town to Upland Rd. because it was said, “Walley” was too easily confused with “Walnut.” (As in this case, Brookline’s newer streets were typically called Road while the older ones typically were Street or Place or Avenue; the town’s first officially named streets in the 1840s included not a single “Road.” The later preference for “Road” may reflect that word’s more rural connotation vs. the urban “Street.”) The lower section of Upland (then called Harvey Ave.) was in place on the Wright Estate by 1877. The Stick Style house at 36 Upland was built in 1877-78 for N.C. Towle, a homeopathic doctor. Later it was occupied by Dr. Joseph Pratt, who subsequently moved up the hill to 94 Upland — following a practice still common in the neighborhood. 30 Upland was constructed the next year for the local postmaster. Later it was occupied by Robert Lincoln O’Brian, former personal secretary to Grover Cleveland, and president and editor of the Boston Herald.
As an “advertisement” for the quality and character of his development, Philbrick had Ware & Van Brunt design 43 Upland (ca. 1876), with its elaborate Stick Style porch, facing the church and flanking the entrance to Upland Rd. This house, together with 84 Upland, also by Ware & Van Brunt, as well as 70 Upland and 167-169 Walnut, both designed by Cabot & Chandler, are the only Philbrick buildings with known designers. Their details are strikingly similar to those of other Philbrick buildings for which no designer has been identified.
39 Irving before it was “updated” in 1917 by the removal of its entrance portico and open terrace, its roof cresting, and the pointed lower terminations of its wooden upper cladding. Note that the then still open landscape of the Philbrick Estate is visible to the right of the house. The young tree at the tear in the photo is probably the towering ash still in that location. The rustic lattice fence on the retaining wall to the left was a type then common in the neighborhood. When the house was built the lot was smaller than now — ending where the retaining wall begins (the former Brookline-Roxbury town line). The side yard extension to the left came from the Brookline Land Company tract.
76 High (1880), is one of the most unusual buildings in Brookline. Built for Edward Stanwood and designed by Clarence Luce, it is a true example of the English Victorian Queen Anne style, which inspired the American version of Queen Anne. The tile roof and tile siding are typical of the English Queen Anne but the roof tiles were unusual here and such typical English “tile hung” siding was almost completely unknown in the U.S. Also characteristic of the English Queen Anne are the decorative terra cotta and carved wood panels, and the typical Queen Anne sunflower design. The gargoyles embarrassed Stanwood, publisher of the extremely influential The Youth’s Companion, who became known as the man with “the house of sunflowers and devils.” It also has interior murals and a stained glass window by Thomas Wilmer Dewing dating from the time of its construction. The present owners have carefully restored the exterior polychrome decorations, which had all been painted over and have uncovered the Dewing murals and stencil-work decorations that had been covered with wallpaper.
Facing the church on the other side of the entrance to Upland is the imposing 39 Irving (1876), built for James W. Edgerly, a cotton broker, Selectman, and proprietor of the Church. His summer home on Ironbound Island, Maine was later immortalized in watercolor sketches by John Singer Sargent. His daughter Mary Sophronia (Edgerly) Andrews is said to have won the first women’s golf match ever played in the U.S. (at The Country Club). Her daughter Louise lived here for a time after her mother died. Later, as Louise Andrews Kent, she wrote The Brookline Trunk, a children’s book about Brookline’s history, with the turret of this, her grandfather’s house, being the setting for one chapter.
70 Upland (1875), another Philbrick-built house, was designed by Cabot & Chandler. Edward C. Cabot was the father-in-law of Charles Storrow who rented it from 1878 to 1885 before moving to 112 High St. The architect Carl Fehmer, of Fehmer & Page then lived there until 1890. The two-story wintergarden bay was added in 1920 for Eugene Tryon Redmond and his wife Helen Eames Redmond, a pineapple heiress from Hawaii. She became a somewhat infamous neighborhood character. In her later years she was given to jogging (before that term was invented) through the neighborhood in tennis shoes while wearing red cloak. She was remembered, long after her departure, for having actively enforced Massachusetts’ then strict blue laws. (Woe unto him whom she saw mowing his grass on a Sunday! An apologetic policeman would soon be at the miscreant’s door.) And, contra the inclinations of many in the neighborhood, she was also a member of the fanatically anti-communist John Birch Society.
Sometime before 1885, Philbrick built 84 Upland, which he sold to Horace D. Chapin, treasurer of the Eastern Railroad. The present owner has information that 84 Upland was designed by Ware & Van Brunt. 78 Upland was also built by Philbrick and rented to Chapin before he bought 84 Upland. In 1886 Charles and Mabel Foster bought and enlarged it using the architect and neighbor Carl Fehmer. Then, in 1893 they hired Peabody & Stearns to design the large, freestanding music pavilion to the right of the house, which was connected to it by an iron-framed glazed corridor whose roof was made of massive glass slabs. Among other involvements, Charles Henry Wheelwright Foster was at various times president of the Boston Sugar Refinery Company, the Brookline National Bank, and the Chickering Piano Co.
The second next owners were Isadore Braggiotti and his wife Lily (formerly Baroness de Relbnitz — formerly daughter of Mr. Sebastian Schlesinger of Boston). They were both singers who maintained a singular Hindu-vegetarian bohemian household with eight uninhibited musical children who delighted the likes of Amy Lowell and Mrs. Jack Gardner at Saturday musicales in the music pavilion — and various of whom later ran a dance studio a la Loie Fuller over a firehouse, performed in Vaudeville, started a national craze for piano four-hands — and in the case of actress daughter Francesca, married John Lodge, grandson of the first Senator Henry Cabot Lodge and brother of the second. John Lodge was by turns, an actor, Governor of Connecticut, and ambassador to Fascist Spain.
Francesca Braggiotti Lodge, Broadway actress whose ability to serenade urban Italian immigrant voters in their own language helped her Brahmin husband, John Lodge, become Governor of Connecticut.
Edward Philbrick built the Queen Anne 94 Upland (ca. 1886), shortly before he died. Two years later, Thomas Hart Clay, editor of the popular children’s magazine The Youth’s Companion, bought it. He was followed by the Stevenson sisters, who were related to William Sumner Appleton, the founder of the Society for the Protection of New England Antiquities. As a result, SPNEA has a collection of photographs of Pill Hill taken from inside and around this house in the 1890s. They show, for instance, that it and its neighbors had been built in the Philbrick’s orchard of large fruit trees. The next owner was Dr. Joseph Pratt, founder of the Pratt diagnostic clinic at the New England Medical Center. Since the 1920s, a semi-secret, pyramid-shaped closet within the porch roof of this house has been known to a succession of resident children and their neighborhood friends as “King Tut’s Tomb.”
After Edward Philbrick’s death in 1889 his family hired F.L. Olmsted, Sr. to compete the estate’s development plan. The Olmsted plan split Upland Rd. around the Green, which it shows as house-lot #18. The redesigned Upland Rd. was completed the same year. Old town engineering plans suggest the designation of “Maple St.” once began at the Green, rather than at the curve, as it does now
Olmsted’s 1889 plan, which split Upland Rd. around the Green (lot #18), shows the houses already built at that time. As envisioned in the plan, Maple St. would have curved around the east end of the Tappan-Philbrick House and come out on Walnut St. (rather than on Irving, as it now does), where there was to be a heavily landscaped “island” in the middle of the street, screening the Philbricks’ view of their rental properties. It also proposed six larger house lots on the land between Upland and Maple, rather than the eventual eight. Across the green, 51 Upland (1891) is a more typical Shingle Style, but still characteristically restrained, house by William Ralph Emerson. After the turn of the century and into the ‘twenties it was occupied Miss B. Gertrude Hall a practitioner of the then-new (and New Age-ish) “New Thought” movement, a spiritual healing movement distantly related to Christian Science. She lectured in Boston at Metaphysical Hall and gave spiritual guidance to devotees who boarded in the house.
Charles H.W. Foster, hired Arthur H. Bowditch to design the Colonial Revival 57 Upland (1893), where for a time BSO conductor Wilhelm Gericke lived. The present 71 Upland, (ca. 1950), replaced a large house with a wraparound porch that was occupied during the Depression by an old lady and numerous cats. When she died, the house seemed so permeated by “cat” and had so little market value in relation to the taxes that in 1940 her heirs let the Fire Department burn it down for practice.
The flames scorched 65 Upland (1891) next door, which had been bought the year before (for $4,000) by the Drs. George and Olive Smith, young pioneering researchers in fertility at the Free Hospital for Women. This very restrained house with refined detailing, including very thin, bead-edged clapboards, without corner boards, and simple gable over-hang, had been designed by William Ralph Emerson for Miss. Emily G. Denny the sister of Dr. Francis Denny.
The houses on the west side of the Green in 1935, (approximately where the Philbrick’s large barn once stood), from right to left: 57 Upland with Wisteria climbing a now recently reproduced chinoiserie balustrade over the portico; the soon to be scorched 65 Upland; the sadly lost 71 Upland; and 94 Upland, where Dr. Pratt’s daughters recalled growing up in a quiet formal Depression-era household that got along with “only” one or two servants on the third floor (with their tub and toilet in the cellar) — plus a Japanese gardener.
To have an ordinary sized house lot encircled by a street is very unusual and suggests Olmsted may have been hoping “lot 18” would remain open space, even though he did not designate it as such. It was a tended lawn in the 1890s and clearly enhanced the value of the surrounding lots. It was bought by Mabel Foster of 78 Upland, sometime after 1893. She resold to the Town in 1901 when the Fosters left Pill Hill, with the town paying $2,500 and other neighbors paying a comparable amount. Officially on town maps it became Philbrick Square but until quite recently there was no sign identifying it as such; to the neighborhood it was always simply “The Green.” It was never elaborated as a “park” but has always been only a simple open greensward with trees around its edge. The last two huge 120-year old oaks planted by Philbrick were felled just a few years ago. (The benches only date from the 1980s.) It became the symbolic heart of the Pill Hill community. Every Christmas Eve neighbors of all faiths gather there for the annual “Caroling of the Green” and every Father’s Day for over fifty years the neighborhood has had its “Picnic on the Green” with games and pony rides — a tradition started in the 1950s by the Smith children of 65 Upland, as a Bastille Day celebration. Recently, after some spirited conversation, a neighborhood consensus determined that it should officially become Philbrick Green.
Around the Green many of Boston’s foremost late nineteenth century architects are represented, with no ordinary Victorian “plan book” houses. On the east side, 56 Upland (1890), designed by Andrews, Jaques & Rantoul, combines the Shingle Style with a British Arts and Crafts vocabulary just then being introduced in England by the architect C.F.A. Voysey, reflecting the close ties between Boston and the British Arts and Crafts movements. That same year, Andrews, Jaques & Rantoul designed the Shingle Style 52 Upland, based on purely American models. The restrained slate-sided 62 Upland (1890) by Hartwell & Richardson, reflects an unusual influence, Northern French vernacular. In the 1980s its cellar housed the neighborhood’s food co-op.
100 Upland (1889) was designed by Peabody & Stearns for MIT professor Charles Cross, originally with a porte-cochere to the right of the entrance and a widow’s walk roof balustrade. He was succeed by another MIT Professor, William T. Sedgwick, who became Curator of the Lowell institute, a nineteenth century workingmen’s betterment endowment, which in the 1940s gave rise to WGBH as a major force in “educational broadcasting.” Winslow & Walker designed the Shingle Style 108 Upland (1892), for Joseph Walker, Speaker of the Massachusetts House and later a U.S. Congressman. Its small octagonal 1905 conservatory is the sole survivor of several which once graced nearby homes.
107 Upland (1892) was designed by Hartwell & Richardson for F. W. Hobbs, treasurer of Arlington Mills. Until about 1919 it was the home of Mr. & Mrs. Arthur D. Little — he having founded in 1886 the world’s first consulting firm, which still bears his name. For a time the family was joined by his nephew Royal Little, a Harvard student. He later founded Textron, the first corporate conglomerate. The Littles then moved to 5 Maple (1893), a house designed by Peabody & Stearns, blending Shingle Style with Colonial Revival. They were joined there by Mrs. Clara Reed Anthony, Mrs. Little’s mother. She had been a life-long friend of Phoebe Apperson Hearst, the then recently deceased mother of William Randolph Hearst. They had corresponded, visited each other, and were engaged in projects together. When young “Willie” Hearst was in Harvard, Mrs. Anthony tried to keep an eye on him — not too successfully, as he was notoriously “wild.” In 1897 the two women worked on a conference and project for a women's university in Washington DC. They were also identified, together with others, as incorporators of Kindergarten Magazine. Clearly, these ventures were funded by Mrs. Hearst’s vast wealth — and, it is said, she proved her friend and confidant with a monthly stipend, as she did for others as well.
The two Shingle Style houses at 12 & 18 Maple (1893) were designed by Arthur Bowditch, with 12 Maple being his home. The house at the corner of Maple and Irving, 27 Irving (ca. 1888) blends the Shingle Style and Colonial Revival. Arthur Little, of Little & Brown, designed it for lawyer William Swan. Among its unusual features is a curvaceous shingled side-porch, whose roof and walls blend together, and a false dormer on the rear pierced by a chimney. The house pre-dates Maple Street, as can be seen in the Olmsted plan.
In 1891-92, George Moffette, Jr. designed the Queen Anne house at 9 Irving with its staggered butt shingles, “stick” detailing in the dormer, and round tower. Interestingly, Moffette, along with many other Boston design professionals, had once signed a manifesto saying that they would adopt the metric system on July 4th, 1876! This house was built for, and for many years owned by, Dr. E.F. Vickery a prominent surgeon and author of medical texts. He never lived there. It was first occupied by Elias Bliss, a flour merchant, and then by Dr. David Townsend, a leading TB specialist, who eventually owned it.
The north side of Irving was part of the Wright Estate. Arthur Mills, an executive of the Boston & Albany Railroad, hired Peabody & Stearns to design 22 Irving St. (1883), a wonderful Shingle Style house that looks as if it had been miraculously transported from a summer isle in Maine. A former owner, Louise Castle, was Brookline’s first Selectwoman. Her husband, Dr. William Castle helped discover the cause of and cure for pernicious anemia.
The Colonial Revival 14 Irving St. was designed by Julius Schweinfurth. Herbert B. and Sara R Ehrmann lived here. It is typical of the progressive and diverse character of Pill Hill that he was one of Sacco and Vanzetti’s attorneys. She, already a feminist and suffragist of long standing became, at 33, a leader of the Massachusetts Council for the Abolition of the Death Penalty which, after a decades-long struggle, succeeded in ending the death penalty in Massachusetts. She also was a founder of the League of Women Voters in Brookline.
Elizabeth Glendower Evans, who lived on Wellington Terrace, helped organize and fund Nicola Sacco and Bartolomeo Vanzetti’s defense. Anne Norwood (Hallowell) Davis, the Secretary-Treasurer of the New England Civil Liberties Committee, lived at 44 Edgehill, which was also the mailing address for its Sacco and Vanzetti Defense Committee. Herbert B. Ehrmann, who lived at 14 Irving St., was one of Sacco and Vanzetti’s several attorneys. The case inspired his wife, Sara R Ehrmann, to devote her life to ending the death penalty in Massachusetts. Ben Shahn’s poster of Sacco and Vanzetti with Bartolomeo Vanzetti’s last testament.
Brookline Land Company’s development below High St. Allerton St. was the first part to be built out of the Brookline Land Company’s second plan for the area east of High. (For a time Allerton was then still called Irving, together with we now call Irving). Set in the Pond Ave. curve at the bottom of Allerton, where the original lower entry to the Land Company’s unrealized five-acre park was to have been, was the old Ward School. Originally built on Pearl Place in Brookline Village in 1853, it was enlarged and moved in 1863 to this Land Company site. (Buildings were moved routinely in frugal nineteenth century New England; there is an entire street of moved cottages in the Point neighborhood.) In 1888 the school was razed, being deemed incompatible with Olmsted’s design for the Emerald Necklace. The present Allerton Overlook, as Olmsted’s design referred to this site, was recently restored in memory of Louise Castle, Pill Hill resident and Brookline’s first Selectwoman.
Eventually, the Land Company coordinated its plans with those Olmsted drew up for the Muddy River Improvement, now part of the Emerald Necklace — although Olmsted’s first Brookline park plans date only from 1880, well after the Land Company’s second subdivision plan for this area had been laid out by Ernest Bowditch. Eventually, in the 1890s, the Company sold to the town much of what became Olmsted Park, Leverett Pond, and Riverdale Parkway (a former pleasure drive where the bicycle and pedestrian paths are now). One reason this part of the neighborhood was slow to develop is that, before Olmsted’s improvements, the brackish tidewaters of the fetid Back Bay reached as far as the present Leverett Pond.
An 1876 view of the banks of the, then still tidal, mosquito ridden Muddy River. The photographer’s romantic composition suggests a tangled Fredrick Church wilderness — with a small lone figure in the center pondering raw nature — rather than the bucolic landscape Fredrick Law Olmsted and his firm would design in the 1880s and execute in the 1890s, leading to the final development of the of the lower slopes of the Land Company’s tract. Judith Eleanor Motley Low lived at 28 Allerton (1884), the house with the little pepper-pot turret. As a 60-year old widow she founded the Lowthorpe school of Landscape Architecture in Groton Mass. in 1901, the first such school intended to prepare women as professionals. In 1945 it merged into the Rhode Island School of Design and became the basis of RISD’s Landscape Architecture Department. After Ms. Low, 28 Allerton was the home of, Dr. John Rock. He developed the oral contraceptive Pill at the Free Hospital for Women — thus, perhaps, single-handedly justifying the name “Pill Hill.”
31 Allerton (1891), designed by Chapman & Frazer, was the final home of the pianist Helen Hopekirk, who moved here from Walnut. St. 35 Allerton (1892) was designed by the firm of Walker & Kimball. 41 Allerton (1896), by the firm of Chapman & Fraser, was the home of Gorham Dana, an expert of fire prevention who was part of the campaign against triple-deckers. Later he moved to 44 Edgehill. 43 Allerton (1893) was designed by Longfellow, Alden & Harlow, a firm which operated in both Boston and Pittsburg, where it catered to Andrew Carnegie, his foundation, and many of that city’s leading industrialists and institutions.
Charles Knowles Bolton, historian, novelist, and a founder of the Brookline Historical Society, lived in the “cottage” type house at 48 Allerton (1893), designed by William F. Goodwin. Bolton was the librarian of the Brookline Public library and then of the Athenaeum. His publications include Brookline: the History of a Favored Town. 52 Allerton (1894), designed by H. Forbes Bigelow, was the home of Charles Packard Ware, who previously had lived somewhat more modestly in one of the Philbrick houses on Walnut.
58 Allerton St. (1899) was the home of the great African American concert tenor, Roland Hayes, who lived there until his death in the 1970s. It was designed by Joseph E. Chandler, the restoration architect of the Paul Revere House. The lot below Roland Hayes’ house (now part of the Brook house) was occupied by the Trumbell Hospital, also called the Allerton Hospital, a small private hospital — built in the 1920’s and removed by the 1960s urban renewal.
Concert tenor Roland Hayes lived at 58 Allerton St. from 1925 to 1977
Originally called Hill St., Hawthorn Rd. was developed from the Allerton end. The unusual two-color brick, Georgian Revival, 4 Hawthorn Rd. was built for Mrs. Charles Appleton in 1894, based on the designs of Henry F. Bigelow and William Rutan. Later, it was owned by Charles S. Sergeant, an executive of the Boston Elevated Railway Company. His daughter Katharine was a life-long editor of the New Yorker, mother of writer Roger Angell, and wife of E.B. White. The most unusual house on the street is 14 Hawthorn (1896) by Ball & Dabney, inspired at a reduced scale, by the 1803 Federal style Aspinwall house on Aspinwall Hill built by the great grandfather of the first owner of this house.
Across the street is a pair of three-story, 1893, Federal Revival houses turned sideways to face each other at 17 & 21 Hawthorn, designed by Peabody & Stearns for George Hyde Page and his sister Mary Hutcheson Page. George Hyde Page was with the Metropolitan Steamship Company on India Wharf. Mary Hutcheson Page, who had attended MIT, founded the Brookline Equal Suffrage Association, and then was involved in founding the Boston Equal Suffrage Association for Good Government — becoming Chair of its Executive Board and later president. She entertained Emmeline Pankhurst during her 1909 visit to Massachusetts.
The grand, now lost, 1803 Federal style Aspinwall house, on Aspinwall Hill, built by the great grandfather of the builder of 14 Hawthorn Rd. — which echoes, at a reduced scale, the original, including its central pavilion with Palladian windows, the unusual crescent shaped fanlight, and balustraded entrance porch. This original Aspinwall house belonged to the father-in-law of John Tappan’s brother Lewis. John Tappan stayed there while the Tappan-Philbrick house on Walnut St. was being built in the 1820s.
17 Hawthorne was bought by Rich Kent and Louise Andrews Kent in 1923. Rich Kent was an editor of, and sometimes wrote for, The Youth’s Companion and later was an editor at Houghton Mifflin. Louise Andrews Kent, author of The Brookline Trunk and other bookstells of her life inBrookline and on Pill Hill in her memoir Mrs. Appleyard & I. As she recalls it, George Page and his wife, who were her aunt’s friends, “always rented one house and lived in the other.” She writes that they “spent a good deal of time abroad and used to move into whichever house was empty when they came back.” She also says the houses had big sliding doors between the living and dining rooms to accommodate large meetings. Eventually the Kents owned both houses. Rich Kent, through a common ancestor named Remember Kent, was a cousin of Atwater Kent, who made a fortune in automobile ignitions and, more famously, in radios. He financed The Kent Tavern Museum that Louise Andrews Kent established in Vermont. After Rich Kent died in 1943 Louise Andrews Kent opened her house to a succession of young couples as tenants “with kitchen privileges” (which became the title of another of her vaguely autobiographical Mrs. Appleyard books). This was one if five Pill Hill houses in which she lived. In addition to her grandparent’s house at 39 Irving, she was born in a house on Walnut St., lived for a time with her parents in Miss Wood’s boarding house on Walnut St., and eventually spent her last winters in the house of her friend Charlotte Sage on Walnut St.
The house at 20 Hawthorne (1899), designed by Edward Little Rogers, was the retirement home of the Rev. Oliver Pomeroy Emerson, born to early New England missionaries to Hawaii in the 1840s. He was sent “home” to be educated. He then returned to Hawaii where he compiled the first English-Hawaiian dictionary. 28 Hawthorne (1911) is by Gay & Proctor. 34 Hawthorne (1915), built for Miss Louisa M. Hooper, the town’s librarian, is by Kilham & Hopkins, who also designed the reform housing on Highland Circle. 40 Hawthorne (1917) is by Dykeman & Murray.
The Free Hospital for Women, now “The Park” condominiums, also developed a Brookline Land Company site, chosen in part for its proximity to Olmsted Park. It was a Harvard teaching hospital which stressed gynecology as a recognized field of medicine, and pioneered radiation treatment of cancer, in vitro fertilization, and oral contraception. The Renaissance-inspired main yellow brick building (1895) is by Shaw & Hunnewell. Major additions were made in1911, 1921, and 1922 by Coolidge & Carlson. Even finer is the nurses quarters facing its main entrance, across what was then still Glen Rd. The landscaping was planned by Olmsted, Olmsted & Eliot in 1893. Beginning in 1895, Charles S. Sargent, who was Director of the Arnold Arboretum for 54 years, became responsible for overseeing its landscaped grounds. The Free Hospital for Women merged with the Boston Lying In Hospital (now part of Brigham & Women’s), which closed its Brookline Campus in the 1960s.
A final Olmsted collaboration with the Land Company occurred in 1894, when it asked the Olmsted firm to draw up subdivision plans for the triangle of land between Jamaica Road and Highland Avenue. Although two studies were completed, nothing came of them, and the property, including the site of the triple-deckers along Jamaica Rd., passed to M.I.T for an athletic field — now belonging to the town and called Harry Downes Field but still also known locally as “Tech Field.