Before being settled by Europeans, Roxbury was made up of forests, rivers, salt marshes, and valleys, with the Roxbury Highlands – present-day Highland Park – the high points of a series of hills. The Massachusetts Bay Company established a farming village here in 1630, and Roxbury’s first meeting house was built in 1632 in present-day John Eliot Square. At this time, Boston was a peninsula, with Roxbury at the edge of the mainland. Boston was connected to the mainland by a very narrow strip called "The Neck," which was later augmented by landfill to create the geography we know today. The "Neck" ran along present-day Washington Street; Highland Park overlooked the marshy area surrounding the road. In 1673 an inter-colonial postal system was established, and Centre Street became part of one of the first routes. By the early 1700s, stone markers were being established. Many were commissioned by Paul Dudley, Chief Justice of the Province of Massachusetts, and some, such as the famous "parting stone" in Eliot Square, bear his initials. Roxbury Highlands was strategically important during the Revolutionary War, thanks to its view over Boston and the Neck. The highest point in Highland Park was fortified in 1775, and the area between Cedar, Highland, and Linwood Streets was also made into a fort. John Eliot Square was destroyed during the Revolutionary War, but rebuilt after the war; the present-day First Church was built in 1804.  

Through the early 1800s, Roxbury was still a farming community, though several merchants created rural estates for themselves along Highland Street and Fort Avenue in 1825. By the 1830s, more and more commuters were living here, and larger estates such as the Alvah Kittredge Home were built. By the late part of the nineteenth century, almost all of the streets we know today had been laid out. In the early part of the twentieth century, Roxbury Highlands began to attract African-Americans and by the 1950s, the area was predominantly African-American. Multiple-unit homes were built, and larger buildings were subdivided. Later, Roxbury Highlands became a neighborhood of very cheap but endangered housing perched above Roxbury Crossing and Jackson Square, whose business districts had recently been obliterated to make way for the proposed Southwest Expressway, which would have sliced its way into downtown Boston. Community organization was able to halt the highway, but many areas that had been cleared were left vacant, and the population of the neighborhood had decreased substantially. The MBTA’s Orange Line was relocated from Washington Street to this now-vacant area – a very controversial move. 

Since at least the 1960s, Fort Hill has enjoyed a somewhat bohemian reputation. Here was founded the Avatar, Boston’s first Underground newspaper, which had to fight the local bluenoses in court for the right to be sold on newsstands. There were communes with colorful names like Rat and Roach Realty Trust, and Prisoners Information and Support Service—PISS for short – a collective of retired draft resisters. A significant number of the people in these early experiments were gay. By the middle of the 1970s a group living in a battered Greek Revival farmhouse near Centre Street began calling themselves the Fort Hill Faggots for Freedom. More and more gays were attracted to the little community, purchasing dilapidated houses – average price $5,000 – in the depressed real estate climate caused by the shocks of busing and arson. At its height the Fort Hill Faggots housed 20 people, in half a dozen houses bunched together near the corner of Gardner Street. While the energy dissipated after a couple of years and the commune disbanded, many of the houses were bought by people living in them, creating the nucleus of a gay community in the neighborhood. 

There are many more stories and histories of our neighborhood. If you have information that you would like to share, please contact the Handbook Committee at 617.442.7925 or leave a message in our box at the Fort Hill Food Emporium. Please also tell us about missing or inaccurate information, and what else you’d like to see in future editions of the handbook.