Rose Fortune was probably mustered at Annapolis at the age of ten. Over time, she established a business of her own. She established herself as a baggage carrier at the Annapolis wharf, and meeting the boats that were traveling from Boston and Saint John. She would transport baggage to nearby homes and hotels, which would include carpet bags, boxes and trunks she would push in her wheelbarrow.

Her business expanded and she also took on the responsibility of waking people up at their inns in time to catch the boat out of Annapolis. Many people depended upon her for this service. As well, along with all this other work, Fortune also became the Police Department of Annapolis Royal, keeping the wharf under control. In time she passed her business on to her grandson, and her descendants still work in the trucking and hauling business.

This 1820's era painting of Rose Fortune is one of the only remaining pictures of a Black Loyalist. (PANS, artist unknown)