Entry No. 28 — the Helena file — filed under: speakeasy
Dorothy's Lounge & Gaming Parlor
Tucked into the historic St. Louis Block on Helena's downtown walking mall, Dorothy's is a craft-cocktail speakeasy that doubles as a gaming parlor, with old arcade cabinets like Street Fighter II wedged in among the vintage decor. It shares its 1882 building with the Windbag Saloon and is named for Big Dorothy Putnam, the madam whose brothel ran on the floor above from 1954 until a 1973 raid shut down what was Montana's last working brothel. Owner Matt Schmechel, who also runs the Windbag, built the place to honor her legacy while pouring original cocktails with creative twists.
The story
In 1973, law enforcement finally shuttered the upper floor of the 1882 St. Louis Block on Last Chance Gulch, ending the run of Big Dorothy Putnam’s parlor house—the last operating brothel in Montana. Dorothy Baker, known locally as Big Dorothy, had run the upstairs establishment since 1954 as a tolerated civic fixture where local politicians, miners, and businessmen quietly slipped upstairs. When the brothel was raided and closed, the ground floor eventually became the Windbag Saloon, leaving the rest of Dorothy's ghost lingering in the brickwork above.
Decades later, Windbag owner Matt Schmechel carved out a dedicated speakeasy space in the historic building to pay direct homage to her. Dorothy's Lounge & Gaming Parlor opened in late 2022, trading glossy modern cocktail trends for rich, dark textures, vintage velvet, and dim red lighting that lean straight into the building's red-light heritage.
The twist is the gaming element wedged into the historic interior. Between vintage wallpaper, plush lounge seating, and craft cocktail prep stations, you’ll find classic arcade cabinets like Street Fighter II running right alongside top-tier drink mixing. It is part historic homage, part speakeasy, and part high-strung button-masher tournament room.
What it's like
Finding Dorothy's means watching for the entrance along the Last Chance Gulch pedestrian mall. Step inside and the atmosphere flips instantly: dim red ambient glow, dark corners, and the electronic chimes of arcade games echoing off old brick. It’s a compact, intimate footprint, so seating fills up fast on Friday and Saturday nights. Grab a stool at the bar, order an original house cocktail, and stake out your turn at the arcade cabinet. Keep in mind the strict schedule—it is closed Sunday through Tuesday, so plan your visit for a Wednesday-through-Saturday night cap.
The move: Order a pair of original cocktails, then settle the night with a best-of-three on Street Fighter II at the arcade cabinet.
📍 Before you go Open Wednesday-Saturday only (Wed-Fri 4pm-midnight, Sat 10am-midnight); closed Sunday-Tuesday.
- 📍 Helena
- 💸 $$
- ⚡ Up for anything
- 🌗 Indoors
Where: 21 S Last Chance Gulch, Helena, MT 59601
Hours: Added 2026-06-24 — confirm current hours before you go.
Pair it with
- Windbag Saloon & Grill — Eat dinner next door in the same 1882 building where Dorothy's brothel once operated before sliding into the lounge for nightcaps.
- Helena Hellbound Ghost Tour — Take a late-night walking tour focused on downtown Helena's red-light and brothel lore before grabbing a cocktail where that history actually happened.
- Reeder's Alley Summer Series & Night Market — Wander the 1870s brick miner's tenements down the hill before walking up the gulch to hit the arcade cabinets.
Good to know
When is Dorothy's Lounge open?
Dorothy's is open Wednesday through Friday from 4:00 PM to midnight, and Saturday from 10:00 AM to midnight. It is closed Sunday, Monday, and Tuesday.
Who was Big Dorothy?
Big Dorothy Putnam (born Dorothy Baker) was the madam who operated a brothel on the upper floor of the St. Louis Block from 1954 until a raid in 1973 closed Montana's last active brothel.
Do I need a password or reservation to enter?
No secret password or reservation is required. Walk-ins are standard, though the parlor fills up quickly late on weekend evenings.
What games are inside?
The parlor features classic vintage arcade cabinets, including retro fighting games like Street Fighter II, integrated right into the lounge area.
Plan a visit & invite your people →
Further reading: Official site · ktvh.com · Wikipedia · Yelp
last checked: 2026-06-24