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 that blew the Ole Bull and the schooner Union out into Lake Michigan. Lady Ann was attempting to make port into Chicago. On board was Captain Easson and a crew of three. The sloop could not make it into the port due to being surrounded by ice. They set anchor and waited for the ice could clear. That night, the wind shifted to blowing directly out of the west.


Lady Ann was anchored near "Mr. Durkee's (or Durfee's) Steam Dredge". The gust of wind broke the dredge from its anchors and it was blown ahead of the gale headed directly for the Lady Ann. The steam dredge cut through the sloops anchor chain releasing it to the elements. The gust of wind blew the hapless Lady Ann off into the night. Captain Easson "had no language to describe the wildness and grandeur of that night voyage." There was nothing the Captain and crew could do, the Lady Ann was powerless in the gale, the wind kept the ships bow into the seas. They lashed the helm and the vessel flew through the darkness of the storm, over huge waves, and through ice. The Lady Ann was "a plaything of the demons of the storm."


The wind eventually lodged the Lady Ann into an ice field where it drifted for a few days. The stuck vessel was blown in a floating ice field until the field lodged itself about ten miles from shore near New Buffalo, Michigan. Captain Easson and the three crew members walked out across the ice to get their bearings. They made it to New Buffalo. They found that the Lady Ann was lodged in a field of ice between which there was a ten mile gap of open water before another gap of ice and shore. Captain Easson and the crew hastily built a light skiff and got a month's provisions to reach the sloop. They made it half the distance when ice began to form around the makeshift skiff. That night a gale blew up and the skiff was frozen in about a mile away from the Lady Ann. Everyone across the eastern coast of Lake Michigan believed the little sloop was lost.


Captain Easson never gave up, one of the crew in the boat had become overcome with terror had laid down in the boat. Trying to keep theirs and his courage, Captain Easson had in his pocket a bottle of brandy and offered it to the crew. They kept going as the wind increased and drove the outward field of ice to shore, breaking up the thin ice around them and piling up cakes of ice and driving them over their little boat nearly crushing it. When daylight broke, the small skiff was back at shore. Easson could not convince anyone at New Buffalo to make another effort to reach the frozen Lady Ann. Defeated, Captain Easson walked down to shore to take a farewell glance at the sloop, its mast sticking up above the icebergs with its pennant flying.


Captain Easson and crew returned home to Racine. Afterwards, Easson shared his harrowing tale with a fellow sailor named Horace Van Doozen, who had then offered to join him in a cruise to return to the Lady Ann. They kept their plans a secret from their wives and departed for New Buffalo with a fresh batch of supplies. The two men were able to walk across the ice to the frozen in Lady Ann. The two sailors then set to cutting the sloop out of the ice. Soon after, the sloop drifted out of sight of shore and started the voyage home for the Lady Ann.


Whenever they found open water, they would sail the Lady Ann towards Racine. Sometimes they would only find a small clear spot of water where they could only sail the little vessel in a circle until they froze in again. On their slow voyage, the sailors would amuse themselves with card games and a few songs on a fiddle they brought. On Sunday's they would have their own small church service with a small bible they brought. Eventually, they came across the steam dredge that caused Captain Easson so much trouble frozen on the ice and lifted completely out of the water. An another day they had sighted what they thought was the Ole Bull drifting.


Eventually the Lady Ann arrived near Racine, but they could not make shore due to ice. That night another violent northeast gale blew up. They made sail and cruised the Lady Ann through the ice. The hull of the vessel was reinforced with double sides. In the darkness they once again could not tell if there was a looming iceberg ahead that could shatter the Lady Ann The morning after they heard a train whistle at Waukegan, Illinois. Afterwards the sloop emerged into clear water near shore and they thought they spotted a place where they could beach the Lady Ann, which was also lodged in ice. They then steered the Lady Ann back out into the lake. The storm increased, the shore was lined with ice and vast fields of ice were again closing in.


Losing it, Van Doozen threw the deck of playing cards overboard and he would have thrown the fiddle were it not for Captain Easson's intervention. They consulted their bible. The two sailors steered the Lady Ann toward Chicago. Eventually the Lady Ann emerged from an ice field near Chicago. The problem was the sloop no longer had its anchors. In lieu of this there was a piece of cable that that they made it into a cable and lashed it together and attached a line and lowered it overboard and this makeshift anchor held the Lady Ann while ice drifted past. Another night closed in and a gale blew up. They could not see the lights, lighthouses or piers of Chicago. Suddenly the wind abated, and the men cut the line and they made sail for the "railroad basin" in the dark. They steered for the breakwater, which they could not see, but only could hear with the lake broke heavily. They were worried about missing the harbor entrance and hitting the breakwater. As they neared the breakwater all they could hear was the roar of the lake breaking on it. Van Doozen was at the helm and Captain Easson stood near the jib sheet. They judged what they thought was the harbor entrance and they were correct, and the Lady Ann was in the basin.


After that ordeal, the winter season never ended for the Lady Ann. The sloop departed Milwaukee for Chicago with a full load of cargo on 13 March 1855. The comings and goings of the vessel were not noted for the rest of the 1855 season.
On 20 September 1855, the Lady Ann had wrecked while attempting to enter Kenosha harbor at midnight. The vessel missed the channel and went ashore on the island just outside the entrance. The Lady Ann was pounded to pieces and its mast went over. The crew managed to jump to safety on the North Pier when it struck. The loss is the "noble little vessel". "Peace to her timbers; she withstood the buffetings of the winds and waves for a two weeks cruise in the depth of winter, to meet an ignoble fate on a sand beach.". The property lost aboard was valued at $500.