This three-hour walking tour peels back St. Paul’s polished facades to reveal bootlegger routes, corrupt politics and the bars that sheltered visiting gangsters. Expect historic taverns, architectural stops and local storytelling that connects places to their untold pasts.
More ways to explore the area's outdoor wonders
The tour begins outside the 7th Street entrance to Cossetta’s, where the air tastes faintly of espresso and old wood. You step into downtown St. Paul with a guide who folds the city’s darker chapters into each doorway — bootlegger routes, improvised speakeasies and the pockets of the city that once sheltered visiting gangsters.
Difficulty
moderate
Duration
3 hours
Fitness Level
Moderate—able to stand and walk up to 2–3 miles with short periods of standing in bars
Wildlife
History
St. Paul’s identity was shaped by river trade, immigrant communities and a Prohibition-era period when local political arrangements allowed visiting gangsters to operate with surprising impunity.
Conservation
Respect historic interiors and support independent taverns by following venue rules, disposing of waste properly, and choosing rideshare or transit to reduce downtown congestion.
Reserve your spot on the St. Paul Untold Stories Bar Crawl - Secrets Beneath the Surface today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring a government ID
Bars require 21+ ID—carry your driver’s license or passport and keep it accessible for entry at each stop.
Comfortable shoes matter
The route covers uneven sidewalks and short staircases across roughly 1.5–2.5 miles; supportive footwear keeps the evening enjoyable.
Plan for pay-as-you-go
Drinks and food aren’t included—carry a card and cash; some small, historic bars are cash-only.
Use public transit or rideshare
Downtown parking is limited—take light rail or a short rideshare to the meeting point outside Cossetta’s to avoid circling.
Government ID
Required for alcohol service and to pass venue age checks.
Comfortable walking shoes
Supportive shoes handle sidewalks and short staircases encountered between stops.
Layered jacket
Evenings can cool quickly in St. Paul—layers keep you comfortable during outdoor stretches.
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Portable phone charger
Keeps maps, contact info for the guide, and mobile payment active through the evening.