Roxbury, with Jamaica Plain as a smaller community within its boundaries, was a hotbed of Revolutionary activity. Joshua Loring, for example, a prominent citizen and Loyalist, was forced to flee the country, leaving behind all possessions and the grand Loring-Greenough House when he would not renounce his allegiance to the Crown. Nearby at John Eliot Square, the grounds of the First Church in Roxbury were the scene of repeated cannon fire during the siege of Boston, and it was from the Church green that William Dawes began the second leg of his famous Midnight Ride of 1775.
Jamaica Plain developed a character of its own within the larger area of West Roxbury, which severed its ties with Roxbury proper in 1851. Sam Bass Warner, whose book Streetcar Suburbs is helpful in understanding the growth and development of Boston's suburbs, states: "During the 1820s a charming rural village grew up near Jamaica Pond and along the main street, Centre Street, which was formerly the highway to Dedham." This area, which came to be known as Jamaica Plain, was the political and social center of West Roxbury. Jamaica Plain was sparsely populated until the second half of the 18th Century, when the area became a popular location for the summer estates of such notables as Governor Francis Bernard and John Hancock. A series of improvements in roads and turnpikes, ca. 1795-1830s, and the laying of the Boston and Providence Railroad, opened the doors for industrial growth. By the mid-19th century, tanneries and breweries, such as the Haffenreffer Brewery, were familiar sights. In 1873, the citizens of West Roxbury voted to annex the town to the City of Boston.
The most striking physical change for Jamaica Plain occurred in the 1870s when streetcar lines were extended from Roxbury into West Roxbury along Washington and Centre Streets, making the area available to larger numbers of commuters. The streetcar lines dramatically changed the rare by brining real estate speculation, which resulted in increased residential, industrial and municipal growth, thus making possible to many the "ideal" housing opportunities we now associate with suburban life. Warner notes that the suburbanization of Roxbury, West Roxbury and Dorchester occurred in two waves, first from 1865-73 and then during the 1880s-90s. Wit this second wave of development in housing, came dozens of schools, libraries and public buildings, of which the Bowditch School is a prime example. Franklin Park and the Arnold Arboretum were also being planned at this time, again providing evidence of tremendous civic commitment. - 4 May 1989, Leslie Larson and Kimberly Shilland.