by Marcia Butman, Discover Roxbury

HIGHLAND STREET runs from John Eliot Square to the top of Fort Hill, so named because Roxbury High Fort was situated there during the siege of Boston. The street then continues down the hill on the other side until it meets Centre Street. Highland Street travels up the hill passing several large outcroppings of Roxbury puddingstone. The Puritans named Roxbury after these distinctive rocky hills that looked like English pudding.

Highland Street and the surrounding area was farmland until the first quarter of the 19th century. In 1825, Benjamin Copeland, David A. Simmons, Thomas Simmons, Supply Clapp Thwing and Charles Hickling bought a 26-acre parcel of land, laid out Highland Street and Fort Ave and built several houses, including The Benjamin Copeland House (140 Highland Street, c.1828), which still survives. Development was slow at first; in 1832 only four houses were standing on Highland Street. By the mid 1830’s large estate parcels were sold for high quality residences, like the Edward Everett Hale House and the Alvah Kittrdege mansion, both originally on Highland Street.

Improved transportation to Roxbury (the extension of Tremont Street, the Boston and Providence Railroad and the Metropolitan Horse Railway) brought middle class commuters who wanted to escape the city and live in a rural setting in single and double homes on smaller lots. The single family homes reflected the suburban ideals of the time; the two family dwellings heralded the more urban development to come.

A new style of building-suburban row houses-for the middle class aspiring to live like well off urban residents was added to the mix. In the late 1800’s triple deckers and two family houses (that looked like one family homes) were built to accommodate the influx of immigrants seeking homes outside the city. Two examples of triple-deckers are at 103 and 188-196 Highland St. Multi story apartment buildings, a popular form of housing for the middle and upper middle class, were the final building style constructed in Roxbury Highlands. Examples of these can be found at 67-77 and 50-70 Highland Street.

All the existing streets in Highland Park were laid out by 1870. The area reached its peak of development by 1900. After that houses were subdivided so that they would be more affordable, but relatively little new building was possible since no vacant land was available.

Since its development in the early 1800’s the population of the Highlands has been a fascinating mix of class and ethnicity that can only be found in an urban area. In order to maintain this valuable population, the city and community residents are working to nurture and protect it from excessive development and escalating property values.