St. Paul has a darker side than you expect. This 3-hour bar crawl turns downtown history into a guided story walk, with bootleggers, gangsters, and corruption tucked behind the barstools. You’ll visit historic bars and breweries while a local guide connects the dots between names you’ve heard and the places you’d never guess.

I especially like the mix of storytelling + actual stops. You get a live guide, access to the bars, and a built-in drink along the way, so it feels like an evening out instead of a lecture. I also love that the tour leans into the characters that shaped the city, including John Dillinger’s era and St. Paul’s own bootlegger lore.

One consideration: it’s a walking tour built around nightlife, so wear comfortable shoes and plan for alcohol rules. Also, it’s not for anyone under 21.

Key things that make this bar crawl worth your time

• Insider-guided pacing through historic downtown, with a local who can answer the why behind each stop
• Skip-the-line access via an express security check so you spend more time drinking and less time waiting
• Crime stories tied to real places, from Pig’s Eye Parrant to visiting Chicago criminals
• Prohibition-era and underground tales, including tunnels used to evade law
• A brewery-and-cocktail stop vibe, with time for premium beers and craft cocktails at award-winning spots

Where the tour starts: Cossetta’s and the blue cue

You meet your guide outside Cossetta’s in blue, not inside the restaurant. That sounds small, but it matters because the group needs to form quickly before you start walking, and you don’t want to be the person searching mid-departure.

From the start, you’ll get a feel for what this tour does best: it gives context first, then sends you to the site. In other words, you’re not just bouncing between bars—you’re learning how St. Paul’s past hides in plain sight.

The 3-hour plan: a compact night that moves

This crawl runs about 3 hours, which is long enough to hit multiple historic locations but short enough to stay fun. The structure is simple: walking tour through downtown historic districts, then short, story-focused time at each stop.

You’re also getting a practical perk: the “express security check” means you’re not stuck in the longest line. For a bar crawl, that can be the difference between relaxing with your first drink and feeling rushed for the next one.

Expect your group to stay together and your guide to steer the mood. If you like history that’s grounded in places—not just dates—you’ll probably settle into the rhythm fast.

Historic bars with bootlegger and gangster stories

The core appeal is the way the guide ties each bar to the kinds of figures who used St. Paul as cover. The tour leans into bootleggers, gangsters, and the corruption thread that ran through big cities and also found ways into the Twin Cities.

You’ll hear about criminal hideouts and the sort of back-room arrangements that made certain neighborhoods safer—or at least quieter—for the right people. The stories center on names linked to the broader Prohibition-era underworld, including John Dillinger and St. Paul connections tied to visiting criminals from Chicago.

This is where the format really helps you. Standing in front of a bar and learning why it mattered makes the “who did what” part click. You’re not imagining a scene; you’re standing in the city where it could have happened.

Pig’s Eye Parrant, local legends, and how corruption worked

One of the most interesting parts is the balance between famous names and St. Paul-specific legends. Pig’s Eye Parrant is one of those local stories that helps you understand how bootlegging wasn’t just about alcohol—it was about networks, influence, and who you could trust.

The tour also connects the dots between law enforcement and the criminal underworld in a way that feels realistic, not cartoonish. You’ll hear about corrupt officials and unofficial arrangements, which helps explain why some criminals could operate while others got shut down.

For me, that’s the value: you walk away with a better sense of how systems work. The city wasn’t only a stage for crime—it was a living set of relationships, and your guide shows how that mattered.

Underground tunnel systems and the Chicago criminals angle

St. Paul’s reputation is calmer than bigger-city mythology. So it’s fun—and slightly unsettling—to hear how Chicago criminals supposedly used underground tunnel systems to evade law.

Even if you don’t see an actual tunnel entrance up close, the story framework gives you something concrete: how criminals moved, avoided authorities, and used the city’s layout like a tool. You start looking at downtown streets differently, noticing the way older infrastructure can create shortcuts and blind spots.

This part fits the theme perfectly: secrets under a normal-looking surface. It’s also one of the reasons the tour works for true-crime fans who don’t just want headlines, but want the “how.”

Brewery stops, craft cocktails, and premium beer time

This isn’t only a history walk—it’s also a night out. You’ll get craft cocktails and premium beers at award-winning brewery stops during the crawl.

If you’re picky about drinks, I think this format hits a good compromise. You’re tasting along the way, but the tour still keeps you moving and learning. That’s why it’s nice that the included drink is part of the flow: you’re not waiting until the end to feel like the price makes sense.

One helpful detail: wear shoes you can walk in, then treat the brewery stops like your reward. That way you get the best of both worlds—stories in historic places, and a real chance to relax with a good pour.

A practical note on guides: Camille, Dan, and Collin

The biggest difference between a good bar crawl and a great one is the guide’s storytelling. This tour has had standout guides in the mix, including Camille, Dan, and Collin—and the common thread is that they can explain the city while keeping the group engaged.

If you like tours that get tailored to your interests, this is a great sign. One guide can steer toward Prohibition details; another can focus more on the neighborhood legends. Either way, you’ll want a guide who can answer follow-up questions without turning it into a debate club.

What you’ll actually get for $79: value that fits a 3-hour night

$79 per person is not a “cheap drinks” deal. But it can be reasonable if you look at what’s bundled: a live expert guide, access to historic bars, and one complimentary drink during the crawl.

For a 3-hour experience in downtown St. Paul, you’re paying for:

• Guided walking time that turns locations into context
• Skip-the-line convenience
• A guided sequence of bars and brewery stops
• Built-in alcohol service structure (with more drinks available for purchase)

If you were going to pay for a couple of bars on your own anyway, the guiding component is the differentiator. You’re buying shortcuts into stories you can’t easily find on your own once you’re actually in the city.

Who this tour is best for (and who should skip it)

This crawl is a solid match if you like:

• True-crime vibes tied to real local places
• Prohibition-era stories and underground-city themes
• Drinking that’s integrated with learning, not tacked on

It’s less ideal if you want a quiet museum-style experience. This is a downtown bar crawl format, with drinking and movement, and it’s meant to feel social.

Also keep in mind the age rule: it’s not suitable for people under 21.

Small planning tips that make the evening smoother

Bring passport or ID, cash, and comfortable shoes. Cash matters because not every stop is guaranteed to match your card preferences, and bringing it keeps you from scrambling when you’re ready to buy your second drink.

And since it’s a walking tour, I’d pace yourself. One included drink plus purchased drinks can add up fast, especially when you’re on your feet moving between locations.

Finally, go in with curiosity. The best part of tours like this is letting the guide lead you from assumption to understanding. St. Paul has a reputation for calm; this tour shows you the hidden chapters.

Should you book St. Paul Secret Stories bar crawl?

If you want a 3-hour night that mixes downtown drinking with stories you can’t easily piece together alone, I’d book it. The included drink, the guided pacing, and the focus on specific characters like Pig’s Eye Parrant, John Dillinger, Machine Gun Kelly, and Chicago criminals give the whole thing structure.

I’d especially recommend it if you enjoy history with edge—crime-era details, underground connections, and the way corruption and networks shaped what was possible. Just be sure you’re comfortable walking, and you’re going for the bar-crawl energy, not a quiet sit-down tour.

FAQ

How long is the St. Paul Secret Stories Bar Crawl?

It lasts about 3 hours.

How much does it cost?

The price is $79 per person.

Where do I meet the guide?

Meet your guide outside Cossetta’s restaurant, in blue. Do not go inside.

What’s included in the price?

An expert local guide, access to historic bars, a walking tour through downtown historic districts, one complimentary drink enroute, and the tour’s stories (including tales of bootleggers and other figures).

Is the tour suitable for minors?

No. It is not suitable for people under 21.

Is there anything I should bring?

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