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 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.

#speakeasy-bar #arcade-play #craft-cocktails #brothel-history #downtown-helena

Plan a visit & invite your people →

Proof: source 1 · source 2 · source 3 · source 4

last checked: 2026-06-24