The property at 107 South Main Street in Old Town, now the City of Waterloo in Monroe County, Illinois, has deed records dating to 1867, when John and Mary Harms sold it to William and Agnes Lofinck, who in 1871 sold it to Henry Wissmath; it remained in the Wissmath family for more than 70 years. Because little written record survives beyond deeds, much of its history comes from stories passed down among owners. The original building was a single-story structure with a basement, and the second story was added later and is now an apartment. Its original entrance was on the right and led to stairs down to the basement; after the entrance was moved, the basement staircase was relocated and the original entrance was filled with concrete, though the original stairs remain. Throughout its history the building is only known to have been a bar, although its original layout suggests it may first have been used as a store. The original tin ceiling still survives, having changed from an off-white color to gold-brown from smoke over the years. Local memory recalls tavern food such as pickled eggs or pigs’ feet for a nickel, as well as cold cuts and later hamburgers, and the tavern was known for friendly faces and loyal customers. In 1949 it was known as Ira Hutchings Tavern under Ira and Hilda Hutchings, who are said to have built living quarters at the back; after about five years they sold it to Arnold and Dora Ludwig, who sold it less than a year later to William and Esther Lieb. The Liebs operated Lieb’s Tavern for over 20 years, then sold it in 1978 to George and Charlotte Heise, whose Heise’s Tavern lasted 13 years. In 1991 Randy Rehmer bought the building from the Heises and opened Randy’s Double R Bar, which remains a favored gathering place for Waterloo residents.