St. Paul’s bars tell stories you miss elsewhere. I like the simple walking format and the way you hit four bars while learning how alcohol and crime shaped the city. The main trade-off is that it’s bar-focused and includes alcohol options, so it’s not the pick for anyone who wants a strictly non-drinking history tour (and it’s not suitable for people under 21).

You meet on the front steps of the Cathedral of Saint Paul with your guide holding a blue umbrella, then you’re on your feet for about 3 hours. I also appreciate the practical side: bring ID and comfortable shoes, and keep cash on hand if you want extra drinks beyond what’s included.

Quick hits before you go

• Four iconic bar stops tied to St. Paul’s drinking-and-crime story
• Gangster tales featuring names like John Dillinger and Alvin Creepy Karpis
• Pig’s Eye Parrant and Fort Snelling connections, explained as part of the local lore
• Optional 4 pre-paid drinks (one per bar stop, when you choose that option)
• Start with Cossettas and end at the White Squirrel Bar style of finish, then return to the meeting point
• Guides you might encounter include Dan and Collin, who are described as fun and tailored to interests

Meeting on Cathedral Steps and Getting Oriented Fast

This is the kind of tour that gets you moving right away. Your guide meets you at the front steps of the Cathedral of Saint Paul, holding a blue umbrella so you can spot them quickly. From there, you’re walking downtown at a pace that makes sense for both looking around and staying with the group.

I like that this doesn’t start with a classroom feel. You’re already in the neighborhood where the stories live, and the guide can point out what’s around you—building character, bar culture, and how St. Paul’s mood changes street to street. If you’re someone who hates wandering aimlessly, this structure helps you get your bearings fast.

One more practical note: you’ll be on your feet for the full 3 hours, so comfortable shoes matter more than you think. A few minutes of extra walking can feel like a lot when you’re also standing to hear stories and deciding what to drink.

Cossettas to Four Bars: How the Tour Actually Flows

The route is built around visiting four St. Paul bars, each with its own role in the city’s alcohol-and-crime narrative. The tour begins at Cossettas and ends at White Squirrel Bar, with the other two stops in between. That means you can expect some variety—different vibes, different clienteles, and different flavors of St. Paul bar life.

The biggest value here isn’t just the locations. It’s the way the guide connects the dots:

• Alcohol wasn’t only about nightlife; it was tied to work, soldiers, and local power.
• Drinking spaces became meeting points—sometimes safe, sometimes not.
• Over time, the same bars kept serving new generations, which is why the city feels both sleepy and story-heavy at the same time.

If you choose the drinks option, you’re also dealing with one drink per bar stop. That’s a clean structure. It’s not an all-you-can-drink situation, and it keeps the group moving without turning the tour into a slow blur.

Pig’s Eye Parrant and the Fort Snelling Connection

St. Paul’s alcohol story isn’t told as a generic “people drank a lot” timeline. You get specific, local characters. One highlight is bootlegger Pig’s Eye Parrant, tied to off-duty soldiers from Fort Snelling. That detail matters because it shows the social function of drinking: it wasn’t only recreation. It was a routine part of how people met, relaxed, and unwound after duty.

What I like about this angle is that it gives the bars meaning beyond decoration. When a guide mentions a connection like Fort Snelling, it changes how you look at the city. Suddenly, a neighborhood bar isn’t just a place with history—it’s a place that once mattered to real schedules and real people.

And if you’re the kind of traveler who likes “how did that happen?” explanations, this tour gives you story logic. It’s not simply names and dates. It’s cause-and-effect.

Gangsters, Corrupt Power, and the Chicago Link

This tour really leans into the crime side of St. Paul’s drinking history. You’ll hear how a corrupt chief of police helped criminals from Chicago settle in the city, for a price. The point isn’t to sensationalize everything—it’s to show how local power systems shaped what happened on the ground.

The guide also brings up famous gangster names, including:

• John Dillinger
• Babyface Nelson
• Roger the Terrible Touhy
• Machine Gun Kelly
• Alvin Creepy Karpis
• the Barker gang

Even if you only know these names from history books or crime podcasts, you’ll get a sense of why they appear in St. Paul lore. The tour ties them to places and attitudes rather than treating them like distant legends.

One word of caution: this is a story-driven evening, not a courtroom documentary. If you’re expecting careful forensic detail on every case, you might find the pacing more conversational than academic. But if you want the way crime and alcohol culture overlapped in a specific city, that’s exactly the lane this tour takes.

Optional 4 Drinks: What You’re Really Paying For

You can do the walking tour with or without pre-paid drinks. If you pick the option, you get 4 drinks total, generally treated as one drink in each bar you visit. That’s useful because it removes decision fatigue. You won’t spend the whole tour asking what’s available and how much it costs.

The included drink options are described broadly—cocktail, spirits, or wine, with a wine tasting component mentioned. In other words, you’re not limited to beer only. That can be a big deal if beer isn’t your default.

Here’s the practical value math: at $79 per person for a 3-hour guided walk that includes four bar stops, you’re mainly paying for access—time with a guide, a route that links venues, and the structured drinking option if you choose it. If you were going to order drinks anyway (and you’re comfortable with that), the pre-paid setup can feel like less friction and easier budgeting.

If you skip the drinks option, you still get the four-bar storytelling and visits. Just plan on paying for anything you order at the bars yourself.

Price and Logistics: Is $79 a Good Deal?

At $79 per person for about 3 hours, this tour sits in the middle of the “guided activity” pricing range. The question is what’s included. You get:

• a local guide
• a walking tour
• visits to four St. Paul bars
• 4 drinks if you select that drinks option

In plain terms: you’re paying for a guided route and the access to four bar interiors. Walking by bars on your own is easy; walking by bars while someone explains why they matter to St. Paul’s alcohol and crime story is the part you’re actually buying.

So who gets the best value? People who:

• want a focused plan instead of researching bars one by one
• like storytelling more than museum-style lectures
• are comfortable with a tour that includes alcohol culture
• prefer a set number of stops over wandering

If you’re the type who prefers to drink slowly, take photos, and linger at one place, you might feel slightly time-pressured by the four-stop structure. But the tour’s tight design is also what keeps the whole experience from dragging.

What the Guide Brings: Names, Tone, and Tailored Stories

Guides are a huge part of why this tour is rated highly. Names that show up with this experience include Dan and Collin. The recurring theme is that the guides are friendly and can tailor the tour to your interests, which matters a lot for a history-and-bars format.

A bar tour can go two ways:

1) you hear a few facts and keep ordering drinks, or

2) you learn enough to make the bars feel like scenes in a story

From the way the experience is described, this one aims for option 2. You’re not just “touristing.” You’re learning why St. Paul has that “Cheers-style” sense of character—multi-generational bar culture where decades matter more than calendar years.

If you like people who can adapt—spotting whether you care more about bootlegging, law enforcement corruption, or famous names—this tour’s guide approach is a strong selling point.

Practical Tips for a Smooth Evening in St. Paul

A little prep makes this tour much more comfortable.

Bring:

• a passport or ID card (because it’s not suitable for those under 21)
• cash (especially if you want extra drinks beyond what’s included)
• comfortable shoes (you’ll walk for the full 3 hours)

Plan your expectations:

• This is a walking route with four bar stops, so expect standing, listening, and moving on.
• If you choose the drinks option, pace yourself. You’ll likely have drink service tied to each bar, and you’ll be walking afterward.

Know the basics:

• The tour is in English and led by a live guide.
• It’s described as wheelchair accessible, which is a real plus for travelers who need accommodations.

And yes, you’ll walk enough that your feet will remember it. Pack your best walking shoes, not your “looks good in photos” shoes.

Who Should Book This Tour (and Who Should Skip It)

This experience fits best if you want:

• a guided way to see St. Paul bars without guessing
• crime and alcohol stories connected to real local figures and locations
• a set route that ends back where you started, keeping the night easy

It’s not the best match if:

• you want a purely non-alcohol history experience
• you dislike bar interiors as part of the sightseeing
• you’re under 21 (the tour isn’t suitable)

If you’re traveling as a couple, with friends, or as a solo traveler who enjoys conversation, this tour can be a fun social blend. You’ll also appreciate it if you’re the kind of person who likes “local lore” and the characters behind it, not just generic facts.

Should You Book the St. Paul Drinking History Walking Tour?

Book it if you want St. Paul to feel alive. The mix of four bar stops plus gangster and bootlegging stories turns ordinary streets into a timeline you can walk through. The optional 4 drinks are a straightforward add-on, and the guide-led format helps you make sense of why these bars matter.

Skip it if you’re looking for quiet, museum-style history or if alcohol-focused stops aren’t your vibe. This is an evening plan, not a daytime culture march.

My bottom line: for $79, you’re paying for a guided route that connects places to stories, with the option to make it a proper bar outing. If that’s your kind of travel, it’s a solid choice.

FAQ

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

The tour lasts about 3 hours.

How much does the tour cost?

It costs $79 per person.

Is this tour with or without drinks?

It’s offered with or without pre-paid drinks. The drinks option includes 4 drinks total, one per bar stop.

Where do we meet and where does the tour end?

You meet at the front steps of the Cathedral of Saint Paul, and your guide is holding a blue umbrella. The tour ends back at the meeting point.

Which bars are included?

You’ll visit four St. Paul bars. The tour starts at Cossettas and finishes at White Squirrel Bar.

Who can participate?

The tour is not suitable for people under 21.

Is the tour in English, and is it wheelchair accessible?

The tour is in English and it’s described as wheelchair accessible.

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