Loyal listener Cathy Harrington lives in Holden, Mass., but her curiosity knows no borders. She recently reached out to WGBH's Curiosity Desk with a question about a Boston neighborhood.

"Why is Jamaica Plain called Jamaica Plain? It's obviously not in Jamaica, and it's not a plain because it's quite hilly."

Let’s begin with what we know for sure.

"Jamaica Plain has never been its own town," said Gretchen Grozier, president of the Jamaica Plain Historical Society. "It was part of Roxbury in 1630 when Roxbury was founded."

In those days, Roxbury was big — encompassing present day Roxbury, West Roxbury and Jamaica Plain. The landscape was varied, and travel was hard. And so, distinct communities quickly began to form in pockets throughout Roxbury, including present day Jamaica Plain.

"This was out by the pond," said Grozier. "You see it on maps called 'Pond Plaine' because it was by the pond, and it’s relatively flat compared to the rest of the Roxbury, which is quite hilly."

By the 1670s and 80s, the neighborhood had truly come into its own. The names "Jamaica" and "Jamaica End" also start appearing to describe it. Eventually, of course, Jamaica Plain would win the day, borrowing the "plain" from "Pond Plaine." But where did the term Jamaica come from? It turns out, nobody really knows.

Theory One: Honoring An Island Conquest
"So in 1655, the British actually took the island of Jamaica away from the Spanish," said Grozier.

Jamaica — an approximation of Xaymaca, the native name for the island — had been under Spanish rule since Christopher Columbus' arrival in 1494.

"There is a tradition of naming new places for victories in the British world," said Grozier. "It’s possible that because Jamaica was taken from the Spanish that this was named Jamaica just to celebrate that recent naval victory."

The timing is about right, but Grozier said the connection between this British victory and the emerging Jamaica Plain neighborhood is, at best, tenuous.

"That’s my least favorite theory," she said. "It’s not very exciting."

Theory Two: Yo Ho Ho And A Bottle Of Jamaica
"Theory number two is a fan favorite," said Grozier.

The early English settlers were a drinking lot. Heck, the pilgrims brought three times as much beer on the Mayflower as they did water. The early settlers brewed their own beer, wine and hard cider. But when the British captured Jamaica, a new spirited beverage took center stage in the colonies: rum.

"[In the 1850s] rum is often nicknamed 'Jamaica,'" said Grozier. "That’s where it comes from."

And just like today, it packed a little more punch than beer or wine. Perfect for this part of town.

"Jamaica Plain was known to be slightly more of a hard-drinking area of Roxbury," said Grozier. "It was more rural. The road to Dedham came through here — what’s now Centre Street. So, stagecoaches would have come through here. There were several inns along the way."

Those inns had taverns, and those taverns served rum.

"So, it's said that people in this area of Roxbury drank more Jamaica — or rum," said Grozier.

So much so that it earned the nickname Jamaica.

Thoery Three: The Local Sachem
This one takes us away from the island of Jamaica, and closer to home. Of course, when the English arrived in the New World, this area was already home to thousands.

"In this area there was a band of Native Americans," said Grozier. "They kind of migrated around."

The leader of this group was a sachem named Kuchamakin (pronounced keh-chuh-MAY-kin).

"Kuchamakin headed this group that lived mostly at the mouth of the Neponset River, but they were known to come over and spend time on the pond," explained Grozier.

Just as they did with so many native words, Grozier says the settlers anglicized Kuchamakin's name.

"He was often referred to by the English settlers by the name Chief Jamaica," she said. "So, it’s quite possible — because he was known to sort of be in this area — the label of Jamaica got transferred from him being here to this area he was known to live in."

There are other theories out there, but Grozier says these three remain the most likely. As for getting to the bottom of it once and for all?

"It would be a really wonderful thing if somebody could find a piece of paper that says, 'We’re calling this area of Roxbury Jamaica because... blah,'" she said. "But I don’t know if it’s out there or not."

And that’s just fine with Grozier. She likes to think of Jamaica Plain as Boston’s most unique neighborhood. And she said it’s fitting that unlike neighborhoods like Beacon Hill (named for a beacon atop the hill) and Back Bay (named for what was once the Back Bay) the origins of Jamaica Plain remain shrouded in a unique mystery.