Folk tales and legends about Nanny have converged with historic facts and where the truth ends and myth takes over, is sometimes unclear. Her influence over the Maroons was so strong that it seemed to be supernatural and was said to be connected to her powers of obeah.

A copy of Claude Gayle's original drawing of Nanny of the Maroons, for which Olive Bowen posed.

A famous legend is that during 1737, at the height of the Maroon resistance against the British, Nanny and her people were near starvation. She was about to surrender when, one night, voices from her ancestors told her not to give up.

When she awoke, she found pumpkin seeds in her pocket which she planted on the hillside. Within a week the seeds grew into large plants laden with pumpkins that provided much-needed food for the starving community. In recognition of this, one of the hills near Nanny Town is still known as 'Pumpkin Hill'.

There are two versions of the story of Nanny catching bullets. The first is that Nanny was able to catch bullets with her hands, which, it is said, was a highly developed art form in some parts of Africa. The other account is that Nanny was able to catch bullets with her buttocks and shoot them out again.

Historian Edward Kamau Braithwaite, who Professor Rex Nettleford said was the final arbiter in Nanny's choice as national hero, has suggested that the original story took a vulgar twist as a result of British colonialists being deliberately offensive about her.

Another legend about Nanny is that she placed a large cauldron on the corner of a narrow mountain path. The pot was said to be boiling even though there was no fire beneath it. British soldiers approaching would look inside out of curiosity, fall in and die while others would collapse and fall over the hill.

There have been suggestions that the pot contained special herbs with anaesthetic properties, as Nanny was said to be an accomplished herbalist.

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