The Lady Ann was a small sloop built in Kenosha in 1849. The vessel is sometimes described between being a sloop and being a schooner and sometime described as having two masts instead of one. Being small, the vessels movements were not always mentioned in the news media of the time. The little ship was primarily used to haul small cargos between Racine and Chicago. Lady Ann was first enrolled in Milwaukee in 1854 and was described as "the easiest managed, freest, fastest, staunchest, and prettiest little craft afloat." by one of its captains, Captain Larsen. Due to its size, Lady Ann operated well into the winter months on Lake Michigan. It was known for making regular trips between Milwaukee and Racine during the winter of 1852-53.


On 15 January 1853, Lady Ann arrive in Milwaukee from Racine with a cargo of wood for Morgan & Butler. On 4 February, the Lady Anne passed by Kenosha bound for Chicago. On 3 March 1853 Lady Ann arrived in Chicago from Racine with a cargo of 20 cords of wood, the sloop having met large quantities of ice in the Lake and had challenges entering Chicago Harbor because of the ice that had accumulated near the end of the piers.


On 7 March 1854, the Lady Ann arrived in Milwaukee from Kenosha with a cargo of 20,000 bricks. This was the sloops first appearance in Milwaukee during the 1854 season. On 21 July 1854 Lady Ann departed Racine for Manitowoc. On 1 November Lady Ann was listed as departing Grand Haven, Michigan.



On 21 January 1855, the Lady Ann was in the same gale as the Ole Bull.