St. Paul’s bars tell stories fast. This 3-hour walking tour turns the city’s old drinking spots into a readable map of bootlegging, police corruption, and famous criminals, with plenty of local color. I really liked how guides such as Dan (and others like Collin) make the past feel human, not dusty—then you get to see it firsthand as you walk bar to bar.

I also love the flexible format: you can do the tour with or without the pre-paid drinks, so you can match it to your pace. A small drawback to keep in mind: the whole experience is centered on bars and alcohol culture, so if you want a strictly non-drinking night, you may feel like you’re in the wrong setting even when you skip the included pours.

Key Things I’d Plan Around

• Meet at the Cathedral area, with a blue umbrella guiding you in the right direction fast
• 4 bar stops built around St. Paul’s drinking-and-crime lore, not just a pub crawl list
• Gangster stories include names like John Dillinger and Babyface Nelson, tied to local context
• Optional drink add-on gives you four scheduled drinks across the route
• A guide who tailors the tour to your interests is the big reason the reviews score so high
• Breweries can show up on the route, including stops like Waldmann and Schmidt, with real-world quirks

Why St. Paul’s Bars Matter More Than You Think

If you think St. Paul is just a quieter cousin to nearby big cities, this tour gently punctures that idea. The city’s identity has long been braided with drinking—where people gathered, where deals got made, and where trouble sometimes followed the liquor.

You’ll hear how alcohol in St. Paul wasn’t only about leisure. Stories connect it to bootleggers like Pig’s Eye Parrant, who served off-duty soldiers from Fort Snelling, and to the darker side of the city’s past, including the way crime became tolerated through corruption and payoffs.

Meeting at the Cathedral and Starting at Cossettas

You start at the front steps of the Cathedral of Saint Paul, and your guide will be holding a blue umbrella. That meeting point is actually helpful: it gives you a recognizable downtown anchor before you start walking.

After you link up, the group heads out for the first stop at Cossettas. Think of this as your warm-up: you’ll get the lay of the land, then the guide sets the tone for how the next few bars fit into the bigger story of the city.

Touring the 4 Bars: Gangsters, Bootleggers, and Neighborhood Character

This is where the tour earns its keep. The walking route is designed so you don’t just “hear about history,” you connect it to the feel of real places that still carry local tradition. St. Paul bars often feel multi-generational—places that seem to count their age in decades, not in slogans.

The guide works the route like a timeline you can see. You’ll pick up context about how criminals from Chicago found a home in St. Paul through a corrupt chief of police who allowed it for a price. Then the tour brings in names people recognize from American crime lore, including John Dillinger, Babyface Nelson, Roger the Terrible Touhy, Machine Gun Kelly, Alvin Creepy Karpis, and the Barker gang—treated as characters in a local setting rather than trivia.

And yes, there’s an attitude shift as you go. St. Paul may not chase the flash of a major nightlife hub, but it does deliver that classic “everybody knows your name” vibe. That matters because it makes the stories land better. When a bar feels like a long-running community place, the crime and bootlegging tales sound less like Hollywood and more like what could happen when groups overlap.

Waldmann and Schmidt Stops: Breweries, Even When They’re Not Brewing

One of the best parts of this tour is that it doesn’t get stuck in a single type of drinking venue. Your four stops can include bar-and-brewery energy, which keeps the walk from feeling repetitive.

A couple of route details stood out from the experience: a stop at Waldmann Brewery was called out as a highlight, and a stop connected to Schmidt brewery was noted with an important practical twist. If the route includes Schmidt, it’s not active as a brewery in the way you might picture, but there are bars inside and it still has that layered “where people drank anyway” feeling.

What I like about that kind of stop is the realism. It reminds you that history doesn’t pause when a business changes. People still gather, and places still hold memories, even when the original operation has shifted.

White Squirrel Bar Finish and How to Keep the Night Going

Your tour wraps up at White Squirrel Bar—and then the experience ends back at the starting meeting point area. That structure helps you plan your evening. You’re not stranded at some distant edge of town, and you can decide what you want to do next without guessing how to get back.

Because it’s a 3-hour format, I recommend treating the tour as your “guided first act.” It sets the tone for the city’s bar culture and gives you names, locations, and story threads you can use later if you choose to continue exploring on your own. If you’re the type who likes to do one curated thing before switching into free mode, this pacing fits well.

The Drink-Option Math: Four Planned Pour-Points

This tour is priced at $79 per person, and what you get is closely tied to whether you choose the drink add-on. The baseline includes a local guide, the walking tour, and visits to 4 St. Paul bars. If you select the option, you add 4 drinks, one in each bar visited.

That bundled structure is the value play. Instead of thinking about what you’re ordering every stop, you can keep your energy steady and let the guide point out what matters about each place. I also like that it reduces awkward decision-making mid-walk—especially on a tour where you’re listening closely and moving at the same time.

If you skip the drink option, the tour still makes sense as a storytelling walk. You’ll still get the crime-and-bootlegging narrative, the bar atmosphere, and the chance to see how these venues function as community anchors. The only consideration is simple: this is an alcohol-culture tour, so the vibe will assume you’re at least comfortable around bar settings.

What to Wear, What to Bring, and How Long It Takes

Plan for comfortable shoes. You’re walking between four venues and you’ll be on your feet long enough to make footwear matter. The format is designed for a relaxed stroll, but it’s still a real walking tour.

Bring a passport or ID card and cash. You can expect that additional drinks are available for purchase, but they’re not included beyond the optional four-drink add-on. Also note the basic age rule: it’s not suitable for people under 21, so plan accordingly.

One more practical point: the tour is wheelchair accessible. If mobility is a factor for you, this is a meaningful detail rather than an afterthought.

Who This Tour Fits Best (and Who Might Want a Different Plan)

This tour is a great match if you like history that has personality—stories with characters, motivations, and places attached to names. If you’re the kind of traveler who remembers a city by its neighborhoods and the people who shaped them, the bar-based approach will click.

It’s also a smart fit for couples, small friend groups, and solo travelers who want a social setting without needing to “party” to have fun. The guides can tailor the tour to your interests, which helps if you’re more drawn to gangster lore than bootlegging, or vice versa.

If your ideal vacation day is quiet museums, you might find bar concentration a bit much. And if you’re very sensitive to alcohol culture even when you skip drinks, you may prefer another kind of walking tour that focuses on non-bar history.

Should You Book This Tour or Choose Another Way Through St. Paul?

I’d book this one if you want an easy-to-follow 3-hour plan that shows you St. Paul through the places locals actually visited and kept visiting. The guide quality is the difference-maker here—this tour stands or falls on storytelling, and names like Dan and Collin came up for a reason: the tours feel lively and responsive.

Book it if you like the idea of linking famous crime names to real, specific St. Paul locations and seeing how community gathering spaces can reflect both charm and controversy. Skip it if you want history without alcohol-world context. But if you’re okay with bars as the delivery system for the story, this is a strong value way to spend an evening with your brain switched on.

FAQ

How long is the St. Paul Drinking History Walking Tour?

It lasts about 3 hours.

Where do I meet the guide?

Meet at the front steps of the Cathedral of Saint Paul. The guide will be holding a blue umbrella.

How many bars do you visit?

You visit 4 St. Paul bars during the tour.

Is the drink option included in the price?

The standard tour includes the guide, walking tour, and bar visits. The 4 drinks are included only if you select the option during booking.

Are extra drinks available to buy?

Yes. Additional drinks are available for purchase and are not included beyond the selected drink option.

Is this tour suitable for people under 21?

No. It’s not suitable for people under 21.

What should I bring?

Bring a passport or ID card, comfortable shoes, and cash.

Is the tour wheelchair accessible, and is there cancellation flexibility?

The tour is wheelchair accessible. It also offers free cancellation up to 24 hours in advance for a full refund.

If you tell me the month you’re going and whether you plan to choose the drink option, I can help you think through whether this is best as your first St. Paul evening or as a mid-trip add-on.

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