This Oskaloosa property housed a wide range of civic and commercial activity over time. In 1896 it contained two saloons, The Senate and The Golden Palace, and The Senate's owner, Henry Van Vliet, became involved in an 1898 federal court case testing Iowa's state Prohibition laws against federal Interstate Commerce laws. McGregor Furniture was founded here in 1896, originally handling both furniture and undertaking, and the business was still operating in 2018 under descendants of J.R. McGregor; the store also had the first elevator in town and in 1913 hosted a "Free Day" event named for a sewing machine company. In 1912 the Knights of Pythias, one of Oskaloosa's most prominent lodge organizations, established its ballroom and membership quarters on the third story of the Malcolm Building, drawing over 5,000 people to its grand opening. Horse-drawn trolley service began in Oskaloosa in 1888, changed to electric street cars in 1897, operated in front of this property, and ended in 1925. Oskaloosa Downtown Development bought the property in 2008 to help preserve these historic structures and renamed it Trolley Place in 2012.