This gracious, historic residential neighborhood illustrates Miles City's prosperity as it evolved from a frontier town into the livestock, transportation, commercial, and governmental hub of eastern Montana. Businessmen and community leaders built most of these homes between 1880 and 1890 and again from 1900 to 1915—prosperous years sparked by the arrival of the Northern Pacific Railroad in 1881 and the Chicago, Milwaukee, St. Paul, and Pacific Railroad in 1908. The neighborhood took shape before automobiles became common. Carriage houses reflect construction during a pre-car era and distinguish it from other neighborhoods. Residents often sought design assistance from architects, including Charles S. Haire, David and Brynjulf Rivenes, and Byron Vreeland. Owners wanted stylish homes that conveyed a sense of culture, beauty, and community stability. Queen Anne towers, stained glass, spindlework, and shingles are common in many early structures. Later, more restrained symmetrical Colonial Revival and Renaissance elements, as well as Craftsman style features, were used. At the height of Montana's homestead boom in the teens, Miles City was bulging with people. Allied in style and origin, the homes of the Carriage House Historic District reflect the community pride and optimism present during one of Miles City's most confident periods of growth.