And here's Olive Lewin's (Jamaican musicologist, 1927-2013) take on it:

//
A Maroon play song: a plantation work song

Most Jamaicans know "Hill an' Gully Rider" as a work song. It, however, started life as a rather athletic game played by men and boys in western Maroon towns. Considering the terrain of the country in which they live, it is quite conceivable for them to have invented a game in which the players' movements simulate the jagged outlines of the hills.

For this game, players hold hands in a curved line. One by one they alternately leap over and pass under the chain of hands without breaking it. In call and response style, the leader is answered by the chorus singing "Hill an' gully".
...

I have never heard this game played beyond the limited Maroon area of the Cockpit Country.

(Lewin, Olive. _“Rock It Come Over”: The Folk Music of Jamaica._ Kingston: University of the West Indies Press, 2000.
//

Per my comments upthread from 2010, I'm not sure that today's Jamaicans would necessarily still know "Hill and Gully" as a worksong or necessarily anything about its history, but I'm pretty sure that early 100% of people raised in Jamaica know the tune because it is ubiquitous in the Jamaican soundscape, even if only heard quoted in recorded popular music.