Jamaica Plain as many other places in Massachusetts, (Martha's Vineyard for example) has a name who's origin is lost in the mists of time, and just as many fanciful theories that try to explain it. JP, as it is know to the initiated, is a funky neighborhood of Boston that, while still being quite urban, has retained a bit of its remoteness, character and wide open spaces thanks in part to a failed urban renewal project that included the building of an eight lane highway right through it. JP has also attracted over the years the kind of intractable granola types that have kept it diverse and eclectic even in the face of crushing gentrification. It is also, though only anecdotally, Boston lesbian neighborhood (the South End being the male gay enclave).
JP was established in the 1630s within the town of Roxbury and the first refence to its name is present in a deed from 1677 that refers to the "Jamaica End" and another deed in 1689 notes the area as "Jamaica or the Pond Plaine".
There are four common explanations for the name, none of which I feel hold much water:The drunkard theory - This one goes something like this, the local population liked their Jamaica rum served Plain since many of them were profitting from the brisk trade in molasses, sugar, rum and slaves opened up since the consolidation of British rule in Jamaica by 1664. The two deeds show clearly that the Plain portion of the name was a geographic reference and the economic center of the neighborhood at the time was farming. Any self respecting rum-runner would have been living in Boston, close to the harbor.
The wayward londoner theory - This one is a duesy. The yarn goes that the londoner told his wife he was going to Jamaica but when she follows him there, he is nowhere to be found, then for some reason she ends up in Boston and hears that near the Pond plain there is this guy, talking about going to Jamaica, all the time. She goes to him and thereafter, the region is called Jamaica Plain. Right.
The Indian drunkard theory - This one tells the story of the local Pond Plain indians that so loved their rum that the phrase "Indian love Jamaica", as it was commonly referred to, brought about the name.
The "I can't really pronounce your name" theory - Postulates that the name Jamaica has nothing to do with the island and is instead a bastardization of either Kuchamakin regent for the local Sachem (chief in the language of the native Massachusetts), Chikatabut, or, more likely Kumachakin's wife, Jamoco.
My money is on the last one, yet people are still unwilling to give up the romantic notion of rum runners turned magnates in their fabulous victorian summer cottages. | 
