Est. 1909 · Trainor Hotel burned 1909 · Speakeasy operated here during Prohibition · Charlie Klein, bootlegger, connected to property; died by suicide 1933 · Featured on Ghost Adventures (Travel Channel), Paranormal State (A&E), My Ghost Story (Biography Channel)
The two-floor bar at 375 E Main Street occupies land with a documented history of fire and hard luck. The Trainor Hotel stood on this property and burned in 1909 — an event that anchors the site's dark record. TBR News Media documentation confirms the 1909 hotel fire. Some accounts also note a possible hospital use of the land during an earlier period, though this has not been confirmed in primary sources.
During Prohibition, the address operated as a speakeasy. Charlie Klein, described in local accounts as a bootlegger and bartender who had partial ownership or operation of the hotel, was tied to the business. Klein served time in prison — reportedly connected to selling alcohol to an IRS agent — and died by suicide in 1933. His house stood across East Main Street from the bar. Klein is the named figure most frequently associated with the haunting accounts.
Katie's of Smithtown has operated as a bar and live music venue on this site for decades. The building's paranormal reputation attracted investigators from three different television programs: Ghost Adventures (Travel Channel, episode filmed October 2013), Paranormal State (A&E), and My Ghost Story (Biography Channel). Ghost Adventures producer Zak Bagans cited Charlie Klein specifically when scouting the location.
Sources
- https://tbrnewsmedia.com/something-strange-in-a-smithtown-watering-hole/
- https://patch.com/new-york/smithtown/ghost-adventures-stirs-up-activity-at-katies-bar
- https://kerriannflanaganbrosky.com/the-books/historic-haunts-of-long-island/
Glasses and objects flying off bar and tablesFigures in late 19th-century clothing on both floorsWoman apparition on basement stairsDistorted faces appearing in mirrorsVoices of women and children in empty roomsTransparent figures captured in photographs
The bar's most-cited physical phenomena is objects moving without apparent cause. Witnesses — including staff and regular patrons — have described glasses flying off the bar and tables; objects falling from racks; and items found displaced. The TBR News Media account and local press confirm these reports from multiple independent witnesses over time.
Apparition accounts are specific enough to carry some weight: figures in period clothing consistent with the late 1800s or early 1900s have been reported on both floors. A woman on the basement stairs is among the most consistently reported encounters — described by staff as ascending and descending the staircase at times when no one is in that part of the building. Distorted faces have appeared in mirrors, and patrons have taken photographs showing transparent figures in the background of selfies.
The Ghost Adventures crew, filming in October 2013, documented voices described as women and children — activity the crew noted was somewhat different from what they had been briefed to expect. Owner Brian Karppinen told Patch that the crew 'got activity right away.' The specifics of what was captured on camera were not disclosed before broadcast. Paranormal State and My Ghost Story both visited and documented their own findings.
Charlie Klein is the figure most identified with the activity. His death by suicide in 1933 is a documented record; the framing here omits method details per editorial standard.
Notable Entities
Charlie Klein (Prohibition-era bootlegger associated with the address; died by suicide 1933)
Media Appearances
- Ghost Adventures (Television, 2013)
- Paranormal State (Television, 2011)
- My Ghost Story (Television, 2012)