HauntBound archive · catalog record
Reported phenomena — as catalogued
1898 Main Street hotel, once the Leighton, with a long-running story of a woman in period dress
501 Main St, Miles City, MT 59301
Research updated June 2026
Age
All Ages
Cost
$$
An operating historic hotel with a lounge and restaurant. Room rates apply for overnight stays; the lobby, lounge and dining room are open to the public during business hours.
Access
Wheelchair OK
Paved Main Street sidewalk; historic multi-story building
Equipment
Photos OK
Est. 1898 · National Register of Historic Places (1988) · Main Street Historic District · Railroad-Era Hotel Architecture
The Olive Hotel stands at the corner of Main and 5th in downtown Miles City, the Custer County seat in southeastern Montana. According to Historic Montana, Joseph Leighton built the hotel in 1898–1899 and it was first known as the Leighton; within a few years his son Alvin took it over and renamed it the Olive.
The Chicago, Milwaukee and St. Paul Railway arrived in Miles City in 1908, and the resulting economic growth prompted an expansion. Architect Brynjulf Rivenes, who designed in a Commercial and Renaissance Revival style, drew the new facade and a three-story addition at the rear; concrete garages were added in 1908 and 1912. The Olive was added to the National Register of Historic Places on October 13, 1988, and counted as a contributing property to the Main Street Historic District the following year.
A popular naming story, repeated in some tour and tourism listings, holds that the hotel was renamed in 1908 for a daughter named Olive Kennie after the Kennie family bought the property. Historic Montana's account instead credits the Leighton family with both the building and the renaming, so the Kennie version is best treated as local lore rather than documented fact.
The hotel still operates with guest rooms, a lounge and a dining room, and keeps period features including its lobby and one room maintained in turn-of-the-century condition. Historic Montana frames the surviving building as a marker of the region's post-World War I economic decline.
Sources
Stories about the Olive circulate in Miles City as one of the town's standard haunted-hotel tales. A local paranormal group records sightings of a woman in period dress in the building and a toilet that flushes on its own, and notes the hotel's history is said to include several deaths and at least one murder, though specific names and dates are not documented in the accounts.
Some versions tie the resident spirit to the name Olive, the figure the hotel is popularly said to be named for. The story also appears in Karen Stevens' book 'Haunted Montana,' which keeps the Olive in regional collections of Montana ghost lore.
The building's genuinely documented history — an 1890s railroad-era hotel still in operation, with original rooms preserved — gives the folklore its setting. The supernatural claims themselves remain undocumented sightings rather than recorded events, the kind of accumulated atmosphere common to old Main Street hotels.
Media Appearances
Stay overnight in the 1898 hotel on Main Street, which still operates with guest rooms, a lounge and a dining room. The building keeps period features in its lobby and one room maintained in turn-of-the-century condition. Book by calling the hotel directly.
Visit the public spaces of the Olive during business hours. The lobby displays J. K. Ralston's painting 'After the Battle,' and the dining room and lounge are open to non-guests for a meal or a drink in a National Register building.
Every HauntBound history is researched from documented sources. We clearly separate verified historical fact from paranormal folklore.
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