In 1838, McKendree Moore and his father, Enoch Moore, owned a mercantile store here that continued until McKendree Moore's death in 1840. The Moore family was among Waterloo's first settlers, and Enoch Moore, born in 1783 in the blockhouse at Bellefontaine, is believed to have been the first child of American descent born in this region. John and Mary Harris sold the property in 1867 to John Lofinck, who established the Gast Haus Zum Golden Loewe, or Golden Lion Guest House, and Lofinck sold it in 1871 to Peter Bickelhaupt. In 1887, Peter's son Louis Bickelhaupt and his partner Fred Weisenbom took charge of the City Hotel, operating a hotel, dining room, and bar that became a regular stop for traveling drummers and drew both travelers and local guests; rumor held that the basement was used to stow travelers' horses. In 1920, Louis sold the property to the Lofinck family, and after their business ended it was sold to a group of men headed by George C. Ziebold, when the hotel was briefly known as oil headquarters during a short-lived oil boom. In 1925, Charles Eppinger of Valmeyer bought the property, moved his family into the hotel, rented vacant rooms to boarders, and ran a restaurant and bar downstairs with the help of family members. The hotel's balcony became a popular vantage point for car shows, races, parades, and Municipal Band concerts. During Prohibition, from 1920 to 1933, the space was converted into a grocery store, and after Prohibition ended the bar returned. Lloyd Engelbrecht later recalled working there and remembered the Tuesday night turtle soup cooked by his father, George Engelbrecht, as a favorite during Municipal Band concerts. After the Eppinger family moved away, proprietors including Emil Honnecker, Joseph Davies, Thomas Crois, and Steve Burke owned the hotel. A Ben Franklin Five and Ten store occupied the first-floor space until the 1980s, after which the property was divided between Sally's Hallmark and Heartland Travel; later Vicki's Hallmark occupied both sides until 2010, followed by Bountiful Blossoms until it moved to Mill Street. In 2018, the building was completely renovated, with the second and third floors turned into apartments called The Lofts at City Hotel and the main level becoming home to Shorty's Smokehouse, while original design features including paint colors, the City Hotel signage, the front wood and glass doors, and interior beams from Horn's Feed Mill were retained.