During the summer of 1887, Ben F. Pippinger became Red Lodge’s first teacher, hired to teach the children of the Rocky Fork Coal Company miners opening the area’s first coal mines. Pippinger later ran the Cloverdale Dairy on a ranch north of town. He and his wife Cora built this nine-room gable-front cottage in 1902, as an “in town” residence. The house was for sale in 1904 at an asking price of $2,600, “…furnished throughout and nicely suited for boarding and rooming purposes” because of its interior arrangement around a central hall. John and Mary Conway purchased the home in 1907 for $2,500. Mary operated a boardinghouse, one of the few such establishments in the Hi Bug area, until 1920. Her tenants included school superintendent A. C. Carloon and railway weighmaster John McLennan. The distinctive roofline sets this residence apart from the neighborhood’s twelve other similar cottages. Cornice returns and stained and leaded glass enhance its vintage appeal.