TLDR
Teetotaler founder Simon Benson haunts his 1913 hotel in a black tuxedo, knocking drinks out of guests' hands in the bar he never wanted to exist.
The Full Story
Simon Benson didn't drink, didn't tolerate drinking, and built his hotel partly so Portland would have a respectable place for civilized people to stay. So the version of his ghost that haunts the Benson Hotel is exactly the version you'd predict: a well-dressed older man in a formal black suit, scowling at guests in the bar, occasionally knocking a cocktail out of someone's hand and walking on. He's been doing it since the 1940s.
The Benson opened on March 5, 1913, on Southwest Broadway. Simon Benson, a Norwegian-born logger turned timber baron turned philanthropist, had commissioned it eight years earlier as a French Empire-style showpiece for downtown Portland. He paid for the Benson Bubblers, the four-bowl drinking fountains still scattered across the city, partly because he wanted his loggers to have an alternative to saloons. The teetotaler thing was a fixed point of his identity. That's why the bar haunting plays as funny rather than menacing.
Staff and longtime guests describe him in a black tuxedo on the seventh, ninth, and twelfth floors, descending the main staircase, walking the corridors. One employee saw him in lumberjack clothing instead of evening wear, in the dining room, and watched him walk into the wine storage area and disappear. The wine storage detail is on-brand. He's still patrolling the booze.
The ninth floor has a separate ghost that nobody can explain. A woman staying in a ninth-floor room woke up to a small boy standing at her bedside. She reached for his arm and described it as "solid for a moment, and warm to the touch." He jumped at her face twice, then there was movement at the foot of the bed, and then he was gone. There's no documented child death tied to the hotel. The boy has been reported by other guests on the same floor, with the same description: small, solid-looking, and disappearing into the air.
The cast extends from there. A woman in a flowing white dress walks the lobby corridors. A second woman in a turquoise gown with red rings has shown up as a reflection in the lobby mirrors. A guest with a disability once described a porter who helped him into bed and then vanished without leaving the room. The Benson's staff doesn't promote any of this. The hotel is still a working four-star property, hosts visiting presidents and senators, runs a Palm Court bar that's been a Portland institution for a century, and the ghost stories live in the back-of-house chatter. The bell desk will tell you about them if you ask the right person at the right hour.
The Simon Benson encounters are the ones with personality. The man built a Portland landmark, lived to see it become the city's premier hotel, died in 1942, and apparently came back specifically to keep glaring at people drinking in his bar. A former bell captain liked to point out that the cocktail-knocking incidents tend to happen at the table closest to the staircase, which is exactly the table Benson would have walked past on his way out.
Researched from 7 verified sources. How we research.