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

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Brookline Preservation Commission
The Pill Hill Local Historic District:

The Story of a Neighborhood

Pill Hill is also called High Street Hill. The 50 year old High Street Hill Neighborhood Association is possibly the oldest continuously operating one in Brookline. It was instrumental in the creation of the Local Historic District, and at that time made its boundaries co-terminus with those of the District. Its impressive web site ( contains a wealth of architectural and historical information about the neighborhood, including historic maps and photographs of every house, arranged so that you can “walk” each street, “turning” at appropriate places onto connecting streets.

This study attempts to blend the stories of the neighborhood’s development, its notable architectural heritage, and the families who have lived here and contributed to its special character up through the mid-twentieth century. A useful historian’s axiom says “history” begins 50 years ago. That informed the decision not to mention present Pill Hill residents. Generally multi-family buildings and houses from World War I on have only been mentioned if there was a specific reason.

While this study is based on earlier research and publications by the Preservation Commission and Brookline Historical Society, it is also a product of our age; Our increasing knowledge of Pill Hill’s residents would be impossible without Google! There is sufficient Town documentation to tell us much about who lived where and when. We not only know their occupations (not all doctors) but also their preoccupations — and how they were educated (overwhelmingly a century ago at Harvard — but very many with MIT connections of some sort). Like today’s Pill Hill, in addition to doctors, businessmen, and lawyers, there was a healthy leavening of artists, musicians, educators, and activists.

Dennis De Witt, Roger Reed, & Greer Hardwick — Summer 2009

In the beginning
The story of Pill Hill begins with Walnut St. It was laid out by 1658, as part of The Sherburne Rd. However, there is a reference as early as 1633 to the construction of a cart bridge over the Muddy River and the road probably followed an ancient Indian trail. The Sherburne Rd. crossed Mission Hill from the Boston Neck and then followed in turn what is now Huntington Ave., the lower portion of Washington St., (only later part of the Worcester Turnpike — now Route 9), Walnut St., and Heath St. (the eastern part of which was also subsumed into the Turnpike). As the first westward route from Boston, the Sherburne Rd. played an important role in the earliest history and development of Brookline and New England. It passed through Brookline’s original Town Center where the first 1714 Meetinghouse stood, at approximately 353 Walnut, on part of a lot later long occupied the 1856 First Parish parsonage. (Its sale in 2007 severed a three-century link of that site with First Parish.) A stone marker and plaque there commemorates the location of the first meetinghouse.

Although the small triangle of land where Walnut meets Warren St. is called Town Green, it is not a “Town Green” nor a “Common” in the normal sense of land originally set aside as common open space. Because Brookline was part of Boston, its only true “common” was Boston Common. A 1905 marker on Town Green speaks of the departure of Brookline militia companies from “this spot” for the battle of Lexington. But in 1775 the land still belonged to the Hyslop family, even though apparently there had long been a wooden, one room schoolhouse on it. In 1793 the Hyslops donated to the town that same “triangular plot of land in the fork in the road” — where the Town soon built a new brick school house. Thus it had always been, at most, a schoolhouse site, not a town common.

Brookline’s 1905 bi-centennial program, devotes several pages to the evolution of “Brooklin” to “Brooklyn” to “Brookline,” but also simply calls that piece of land “the Walnut St. Triangle.” In 1910 a D.A.R. patriotic historical magazine article, written by the Brookline chapter’s “Regent” apparently first called it the “Village Green.” Only in 1927 did “Town Green” finally appear in the Town Atlas.

An 1876 view of the 1825 first Town Hall before it was physically incorporated into the present First Parish Church complex. Note the horse sheds to its right, a once common feature of New England meeting houses and churches. During long church services the horses sheltered inside the sheds, with the buggies still attached.
The present First Parish Church site was sold by the Hyslops to the Town in 1805. In 1825 Brookline’s first true Town Hall, now First Parish’s Pierce Hall, was built there. Only in 1833 were Massachusetts towns and parishes finally separated.

Cypress St, the western edge of the Pill Hill neighborhood, was originally New Lane, built in 1720 to connect Walnut St. with Washington St. in Brookline Village across the Town Brook wetlands. Town Brook was and is (now in a big pipe) where the Green Line runs. Cypress St. provided access for the residents of northern Brookline to the new 1714 meetinghouse. South of Walnut, there was only a narrow lane, which wouldn’t even show up on maps (as Sewall St.) until 1855. Although we now think of Cypress as crossing Walnut, the old sidewalk lot lines, still surviving on the northwest corner of the intersection, clearly show that Cypress originally curved westward into Walnut and did not cross it. The present, more squared off curb line at that side of the intersection, was only created in ca. 1980.

Confusingly Brookline as a whole was initially sometimes referred to as “Boston Commons” — the place where Boston kept its “swine and other cattle.” A series of maps of old land ownerships shows an interesting pattern. In the seventeenth century there were many smaller holdings east of Harvard St. and again to the west of Pill Hill and Fisher Hill – although perhaps these holdings were not all settled. By the late eighteenth century there was some reconsolidation of those small holdings into country estates, a trend that would continue through the first half of the nineteenth century.
The Eliphalet Spurr House (ca. 1798) at 103 Walnut is the oldest house on Pill Hill and one of the oldest surviving houses in Brookline. It is a typical vernacular Federal style house with added early nineteenth century Greek Revival portico. In 1816, Spurr, the builder and original owner, established the first line of coaches to run between the Punch Bowl Tavern in Brookline Village and Boston. It lasted only a few years, in part because the fares were considered too high. In 1817 Thomas and Eliza Aspinwall, the son and daughter of Colonel Thomas Aspinwall, purchased it. Thomas was deaf mute, but was active in the town, making himself understood by signs. He and his sister died within a year of each other in the early 1840s. During the 1870s the house was an “infant asylum” — which may have meant something like a daycare.

The Eliphalet Spurr House as it looked ca. 1948. Note the huge elms (sadly lost to the Dutch Elm blight), which gave so much spatial character — like grand continuous outdoor rooms — to the early twentieth century American streetscape. In the distant background to the right is the towering Gothic 1870s Town Hall, (lost to 1960s urban renewal and the popular disdain of the time for Victorian architecture). It stood where there is now an empty space in front of the present town hall.

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