Jacob Weisbord established a brewery near Winona in 1856. Two years later, a larger site was chosen just below the Sugar Loaf (a limestone peak jutting out of the bluffs above the Mississippi Valley), but it would not be until 1862 that the new brewery would be completed. In 1870, Jacob hired brewmaster Peter Bub, who had worked at the Blatz Brewery in Milwaukee. Later that same year, Jacob died and Peter Bub operated the brewery until it burned down two years later. Peter bought the remains from Mrs. Weisbord and rebuilt the brewery, enlarging it in the process. When Peter Bub died in 1911, his son-in-law took over management of the place, renaming it the Sugar Loaf Brewery. It continued operation under different managers until 1973, when the brewery folded.
