Since the 1880s, Miles City has been the trade, service, and social center for Eastern Montana ranchers. After its famed McQueen House burned down, town booster Joseph Leighton built the Leighton, 1898-1899, which became an area landmark. Within a few years his son Alvin took over and renamed it the Olive Hotel. When the Chicago, Milwaukee and St. Paul Railway arrived here in 1908, the thriving economy called for expansion of the Olive, including a three-story addition to the rear. Architect Brynjulf Rivenes designed the new façade, lobby, and the east addition. Now the Olive also housed a cafe, barber shop, cigar and curio stand, buffet, and sample rooms, where ranchers and commercial travelers met. Two fireproof, poured concrete garages built in 1908 and 1912 demonstrate the rising importance of the automobile. The Olive Hotel stands as a symbol of the effects of post-World War I depression on this region. When thousands of homesteaders lost their lands because of drought and falling grain prices, the Olive’s business declined noticeably by the mid-1920s.

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501 Main Street, Miles City, Montana ~ Private