Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Jamaica Plain & Roslindale: Steeple Chase (WTPR#10)

Theodore Parker Church, West Roxbury, Current home of the Second Church of Roxbury.

“In answer to the petition it was clearly voted…that the petitioners together with all such as dwell on the south side of the afores’d line who are willing to joyne with them, and do embody so as to maintain an able learned Orthodox minister amongst them, shall be freed from any charge to the minister of the east end of the town, and also from charge to the repairing and sweeping the meeting house so long as they do maintain a minister among them as afores’d and no longer.”

                                                           Town Records Roxbury February 7, 1711.

This is another of the entries from my previous project, Walking the Post Road, which I have transferred over to this project for two reasons. The first reason is that it is relevant to this project in that it is a ‘ramble’ about Boston. The second reason is that the previous project was done on Apple’s iweb, which is no longer supported by Apple and, consequently, the website is slowly decaying. I will eventually revisit that project and bring the entire site up to date. In the meantime readers are welcome to comment upon this entry as part of the current project. It has been updated and edited slightly from the original version which was published on Tuesday, June 1, 2010, as entry #10, Mile 6.

Milestone 6 is located in a wall on Centre Street, directly opposite Allandale Road in Jamaica Plain. The wall is part of the Arnold Arboretum which I discussed in the previous post. The Arboretum has 265 acres of plants from all over the world, and the Post Road skirts the western border for over a mile. On a fine May day the trees are all in bloom or have leafed out and everything is lush and verdant. From the road I can see directly into the Arboretum. A red-tailed hawk circles over the white pines, and I can smell the scent of flowering plants. For the first time I feel I am heading out of the city. 

          As I walk away from the First Church of Jamaica Plain Unitarian Universalist and the milestone in Monument Square I feel that I am officially “on the road.”  The road here is familiar to me from my time living in Jamaica Plain. For two years I drove this way to the school at which I taught. However I saw nothing from the car. Walking provides a much different perspective. I can linger over a view, I notice things I never would have seen in a car, I can smell the aroma of the plants wafting through the air from the Arboretum. The only indication that I am still in the city of Boston is the loud incessant traffic on Centre Street, which takes the form of a four lane divided road as I make my way through the rotary marking the transition from the Arborway to the Jamaicaway.


Paul Dudley milestone: 6 MILE Boston 1735 PD. In the wall of the Arnold Arboretum opposite Allandale Street, Jamaica Plain. The last extant milestone in the series.

I am using Hales’ 1832 map of Roxbury as my guide on this segment of the walk. It is old enough to predate most of the development in Jamaica Plain and Roxbury, and it is accurate, unlike some of the earlier maps (one map has the road to Dedham skirting the north side of Jamaica Pond for example). The Hale map has all the roads and dwellings extant in 1832. There were numerous additions to the landscape following the Revolutionary War, the most notable on this map being the construction of the Dedham Turnpike in 1803, which cut a straight line through Roxbury directly to Dedham. The distance from Boston to Dedham was reduced by one and a half miles. An obvious question arises from a cursory glance at the route I am following and the route of the Dedham turnpike: why is the “great highway to Dedham” so long and winding? Two words: hills and swamps. The road I am following preexisted the arrival of the English and was presumably followed for centuries on foot by Indians with no pack animals. This road and many like them across North America were developed from centuries of trial and error searching for the easiest route. Although the road I am traveling has hills, it follows the lowest elevation possible, bypassing the steeper hills in favor of a more gradual rise and fall in elevation. The developers of the turnpikes, about which I will have much more to say in future entries, were interested in the shortest route, regardless of obstacles, as the turnpikes were intended for stagecoaches and horses, not pedestrians.


The road along the western border of the Arboretum rises slowly, reaching a plateau at the milestone indicating 6 miles to Boston. The Hales map shows half a dozen buildings along the section of Centre Street which borders the Arboretum. I keep my eyes peeled and think one or two houses may still exist from that period. One is pictured below. One house that no longer exists was situated on the rock outcropping on the southwest corner of Centre Street and Allandale Street, directly opposite the milestone. This was the Peacock Tavern, kept as a tavern by Captain Lemuel Child. Drake states that it was “ a somewhat noted resort,” and George Washington is known to have slept there (seriously, I am not just trying to see if you are still awake) on April 4, 1776 on his way to New York after successfully forcing the evacuation of British forces from Boston on March 17, 1776. The building and forty acres were sold to Samuel Adams, where “here the aged patriot resided during his gubernatorial term, and for the brief remainder of his days made it a summer residence.”1

Detail of Map of Roxbury from 1832 by John Hales, showing the area now comprising the neighborhoods of Jamaica Plain, Roslindale, and West Roxbury. The route followed in this entry follows the ‘Post Road’, or the ‘old road to Dedham’, from the Third Church of Roxbury in Jamaica Plain (near the ‘M’ in Jamaica), along Centre Street to Walter Street, then South Street to the Second Church of Roxbury in what is now West Roxbury (the church at left center), ending just past ‘Willow’ Street at the current ‘Second Church’, the Theodore Parker Church on Centre Street at Corey Street. A newer version of the ‘Third’ Church, , dating from 1853, remains at the same site on the corner of Centre Street and Eliot Street and is known today as the First Church in Jamaica Plain Unitarian Universalist. The ‘Second’ Church of Roxbury was originally located on Walter Street in what is now part of the Arnold Arboretum, but moved to a new location at the corner of South and Centre Street in 1773 (the one shown on the map) after the creation of the ‘Third’ Church. Subsequently the church moved to the building in the above photo on Centre Street at Corey Street in 1890, and is today known as the Theodore Parker Church, a Unitarian Universalist Congregation. The next entry in this series continues the walk to Dedham from the Parker Church along Centre Street to the Dedham line, shown in the map above.


       At the junction of Walter Street and Centre Street I turn left to follow the old road to Dedham as the extension of Centre Street was not built until the early nineteenth century. The road drops here and would have crossed a small brook which fed into the Stony Brook (see Hale map above). The road then rises again as it passes alongside Peter’s Hill, peaking at about one hundred and seventy feet above sea level. On the left is an old stone staircase leading into the back side of the Arboretum, where one finds a few remaining gravestones from a cemetery dating from 1712. The Walter Street Burying Ground was associated with the Second Church of Roxbury,  which had been established the same year. Walter Street is named for an early minister of the Second Church, Nathaniel Walter. I began this section of the walk at the First Church of Jamaica Plain, which was formerly known as the Third Church of Roxbury, and, as I am sure you are now thoroughly confused, I will spend a little time explaining the meaning of all this as it will have a significant bearing on future discussions of the Post Road.

        In order to understand the formation of towns in New England, it is important to understand that the settlement of New England, especially in Massachusetts, was dominated by the Puritans. The settlement of Boston for example, was accomplished entirely by Puritans, who conceived of their community primarily as a congregation. Every person in the community was required to attend services at the meeting house, no matter how distant their residence was from the church. New congregations would be established when the population became too large for the meeting house to hold all of the congregation or when a large enough group of people lived a sufficient distance from the meeting house that they would petition the General Court to allow them to build their own meeting house closer to their residences. An example of the first instance was the establishment of the Old South Meeting House in Boston in 1669. The second example pertained in Roxbury, where the majority of the population lived in the Dudley Square area as discussed in a previous entry. However by 1706 approximately forty-five families lived west of Jamaica Pond. These families would be required to travel from two to five miles to reach the Meeting House in Eliot Square. These families, led by Joseph Weld, “petitioned the General Court to be made a separate precinct, to be freed from taxes for the old parish, and for aid in building a church.” 2 Nothing came of this petition, so the families put up their own money and built a church along with the cemetery mentioned above on land donated by Weld. This fait accompli resulted in subsequent approval of the formation of the new Second Parish of Roxbury.

        The majority of the members typically disapproved of the formation of new congregations primarily because the remaining members would still have to pay for the salary of the minister and the upkeep of the church which meant higher taxes for each member. Such was the case in 1769 when the residents of Jamaica Plain desired the formation of their own congregation, which would be composed of members of both the First and the Second Parish congregations. The Second Parish members in particular were unhappy and would only be satisfied if the departing members would pay for the Second Church to be rebuilt further down the Dedham Post Road, closer to the residences of the rump congregation. Thus, in 1773, the sum of 666 pounds was donated by the newly formed Third Parish of Roxbury to remove the Second Church from its site adjacent to the Walter Street Burying Ground to what is now the corner of South and Centre Streets in West Roxbury (the church is visible on the Hale map).

        The formation of new congregations often was the prelude to the establishment of new towns in New England. West Roxbury eventually became a separate town comprising the Second and Third Parishes of Roxbury. The Third Parish in turn became a separate town from West Roxbury, Jamaica Plain, and all three towns eventually were incorporated into the city of Boston. This pattern of town formation was also followed in Dedham, where virtually every town I will pass through on the way to Rhode Island originally formed a part of the town of Dedham.


The Walter Street Burying Ground contains gravestones dating back as early as 1722. The stone of Captain John Baker has a particularly interesting epitaph: “Life is uncertain, Death is sure; Sin is the cause, Christ is the cure.” The cemetery is on the steep incline of Peter’s Hill, the highest point in the Arboretum. I walk the rest of the way up to the 240 foot summit of the drumlin for a spectacular view back over the Arboretum to downtown Boston. The distance as the crow flies to the John Hancock tower is 4.23 miles from this spot, but it takes closer to six miles to reach the building traveling the route I have followed. I follow the sweet call of a warbling vireo as I retrace my steps to the road.

        The Second Church of Roxbury is no longer adjacent to the cemetery as noted, but the present congregation worships at the building in West Roxbury, and I have decided to end this segment of the walk there, at the corner of Centre Street and Corey Street. There are no more milestones to mark the distance traveled. However the church buildings of many of the early congregations still exist, and I will use the steeples of these churches as my guideposts. The distance from the the First Church of Jamaica Plain to the present Theodore Parker church is three miles, as is the distance between the latter church and the Unitarian Church of Dedham. Thus a typical segment of the Post Road that I cover in one entry will be approximately three miles in length from steeple to steeple.


   Descending the hill on Walter Street I arrive at South Street which originates in Roslindale Square. This intersection is located approximately seven miles from the Old State House. I turn right onto South Street and pass an Orthodox church that would not look out of place in Thessalonika or Kiev or Aleppo. The area on both sides of the road here once consisted of an estate of thirty acres belonging to William Dudley, the younger brother of Paul Dudley, and is referred to in a sale of 1775 as “land both sides of the road to Dedham, seven miles from Boston Town House.”3 The road passes from the neighborhood of Roslindale into West Roxbury around the intersection of South and Centre Streets. The Hale map shows the site of the second building of the Second Parish of Roxbury which served the parish from 1773 until 1890, at this junction. The site, at the corner of Centre Street and Church Street, is now occupied by the parish school for the Holy Name Parish Church (Catholic) located next door.

        I follow Centre Street in West Roxbury as it curves west then south before I arrive at the final resting place of the Second Church of Roxbury at the corner of Centre and Corey Street, in the middle of the commercial center of West Roxbury. The congregation hired Alexander Wadsworth Longfellow (the same Longfellow who designed the Orange line Elevated railroad stations; see entry #4)  to build a new church here in 1890, then replaced it a mere ten years later with the current building, designed by Henry Seaver, which is famous for its set of Tiffany windows. In 1962 the First Parish Church of West Roxbury merged with the Unitarian Church of Roslindale and a decision was made to rename the church in honor of the famous pastor of the church from 1837-1846, Theodore Parker. In the next entry I will discuss Parker and his flock in more detail, as they played a significant role in the cultural and intellectual life of mid-nineteenth century America.

        The Parker Church is located approximately eight miles from the Old State House and three miles from the First Parish Church of Jamaica Plain. I have followed the congregation of Roxbury as it formed in Eliot Square, then split into two, then three congregations. I have followed the Second Church as it progressively moved further away from the original church until I ended up here at the current home of the congregation. Milestones have disappeared but steeples remain, and these guide posts will be significant in the increasingly rural and suburban areas I travel as I follow in the footsteps of the congregations as they too moved away from their original churches to settle in the wilderness.


  1. Samuel Drake, The Town of Roxbury, 1908, 435.
  2. Samuel Drake, The Town of Roxbury, 1908, 448.
  3. Samuel Drake, The Town of Roxbury, 1908, 445.

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