Entry No. 6 — the Helena file — filed under: haunted
Windbag Saloon & Grill
The 1882 St. Louis Block on Last Chance Gulch held a vaudeville-and-burlesque hall and a bowling alley before its upstairs became a working brothel. From the mid-1950s it was 'Dorothy's Rooms,' run by madam Big Dorothy Baker, one of Montana's most famous houses until an April 1973 police raid shut it down. The main floor is now a burger-and-beer saloon, and staff and patrons report perfume with no source, music and female laughter from the old upstairs rooms, a cowboy apparition seen in the dining room at lunchtime, and movement in the mirror above the back bar.
The story
Before you order a burger at 19 South Last Chance Gulch, take a hard look at the back bar and the ceiling line. Built in 1882 as the St. Louis Block, this building spent its early years operating as a vaudeville-and-burlesque hall with a bowling alley underneath. But the building's real notoriety took root upstairs. From the mid-1950s until 1973, the upper floor housed Dorothy's Rooms, an infamous working brothel run by madam Big Dorothy Baker.
Dorothy ran one of Montana's most famous houses of ill repute with high-profile discretion right on downtown Helena's main strip. The arrangement lasted nearly two decades before an April 1973 police raid shuttered the bedrooms for good. The upper level was eventually sealed away, and the street-level space was converted into the burger-and-beer tavern operating today.
Closing the brothel didn't clear out the building. Staff and patrons regularly report unexplained bursts of perfume wafting through the bar with no physical source, as well as faint music and female laughter echoing down from the walled-off upstairs rooms. Watch the mirror above the back bar—bartenders have caught unassigned movement in the glass—and keep an eye out for a full cowboy apparition known to drift through the dining room at lunchtime.
What it's like
Grab a booth along the pedestrian mall, order a burger and a beer, and keep your eyes on the mirror behind the bar while you eat. The atmosphere is standard Montana saloon, but the history is everywhere once you start looking. Before you leave, ask the bartender to point out where the staircase to Dorothy's old rooms used to frame the room before the upper floor was sealed off.
The move: Grab a booth for burgers and a beer, then ask the bartender where the staircase to Dorothy's old rooms used to be.
- 📍 Helena
- 💸 $$
- ⚡ Up for anything
- 🌗 Indoors
Where: 19 S Last Chance Gulch, Helena, MT 59601
Hours: Added 2026-06-24 — confirm current hours before you go.
Pair it with
- Dorothy's Lounge & Gaming Parlor — Sharing the historic St. Louis Block building, this craft cocktail parlor lets you continue exploring the block's red-light legacy right next door.
- Helena Hellbound Ghost Tour — Pick up this guided walking tour nearby on Last Chance Gulch to put the Windbag's haunting into broader context with Helena's dark history.
- The Bullwhacker Statue — Located right out front on the Last Chance Gulch walking mall, making it an easy quick stop on your way into the saloon.
Good to know
Who was Big Dorothy?
Big Dorothy Baker was a legendary Helena madam who ran 'Dorothy's Rooms' on the building's top floor from the mid-1950s until an April 1973 law enforcement raid shut it down.
What ghostly activity is reported inside the saloon?
Visitors and staff report phantom perfume scents, laughter and music coming from the sealed upstairs, a midday cowboy figure in the dining room, and odd movement reflected in the back-bar mirror.
What did the building house before it was a brothel?
Erected in 1882 as the St. Louis Block, the venue originally contained a vaudeville and burlesque hall alongside a bowling alley.
Can you tour the old brothel rooms upstairs?
No. The upstairs brothel rooms are private and closed to the public, leaving only the main-floor restaurant and bar accessible.
Plan a visit & invite your people →
Further reading: Wikipedia · hauntedplaces.org · southwestmt.com · Yelp
last checked: 2026-06-24