Easily spotted from US Highway 61, this rocky hill has been a distinctive landmark long before European settlers came to Winona. Sugar Loaf towers over the city, offering a panoramic view of Minnesota, Wisconsin, and the Mississippi River that forms the border between the two states.
Local Dakota legend claims the bluff was once part of a large mountain that is now split into two parts (the other being Barn bluff in Red Wing, Minnesota). According to the story, there was a dispute over the possession of the mountain, which was a burial site for two Dakota villages.
A battle between the villages would have broken out were it not for one of the chiefs. Chief Wapasha took his cap and waved it to gain the angry crowd’s attention. As the chief threw his hat, the hill was split in two by The Great Spirit and half disappeared. A party of Dakota was sent downriver and found that other part of the hill had been relocated to what is now Winona.
In the mid 19th-century, European settlers began to quarry the limestone of the hill to build the growing city of Winona. This caused the once-rounded hill to become plateaued, with a distinct rock pinnacle. This quarrying lasted until 1887, when the bluff took the familiar shape it has now. Visitors today can hike up the hill and can climb the rock overlooking the city.