St. Paul Secret Stories Bar Crawl – Hidden Tales & History

St. Paul’s most entertaining stories are not told in grand museums. They surface in old bars, back rooms, and streets where bootleggers, gangsters, and local power brokers once crossed paths. This three-hour crawl follows those stories through downtown, with tales of John Dillinger, Machine Gun Kelly, the Barker Gang, Pig’s Eye Parrant, and the underground routes used by Chicago criminals.

I like the local guide-led storytelling and the way the tour connects a drink with the city’s less polished past. I also like the chance to visit historic bars and breweries rather than simply walk past them. The main drawback is that $79 is a serious price if you plan to buy several drinks, since only one drink is included and the exact bar sequence can vary.

Key points to know before you book

• The meeting point is outside Cossetta’s: Look for your guide in blue, and do not go inside the restaurant to find the group.
• The stories center on St. Paul’s criminal past: Expect bootleggers, gang hideouts, corrupt officials, backroom deals, and tunnel routes.
• One drink is included: Additional cocktails, beer, and other drinks cost extra.
• The tour lasts three hours: You will walk between downtown stops, so comfortable shoes matter.
• Guides shape the experience: Camille, Dan, and Collin have each led this tour, with Dan noted for tailoring the conversation to individual interests.
• It is strictly for adults: Every participant must be at least 21 and should bring government-issued identification.

Why St. Paul makes a good setting for a crime story

St. Paul can feel quiet beside Minneapolis, yet its past has plenty of crooked corners. During Prohibition and the years around it, the city became a useful place for criminals who wanted distance from Chicago and room to make deals. That contrast is the hook here: calm streets on the surface, uneasy stories underneath.

The tour focuses on the city’s connections to bootleggers, visiting gangsters, law enforcement, and local officials. You are not getting a broad survey of St. Paul architecture or a standard city walk. Instead, you are following a narrow thread through the city’s past, one tied to bars, money, secrecy, and the people who knew how to work around the law.

I like this approach because the setting matters. A story about a bootlegger lands differently when you are standing outside an old drinking establishment than when you hear it in a classroom. The bars provide a sense of place, even when the history itself is the main attraction.

The experience also includes stories about Pig’s Eye Parrant, an early figure tied to St. Paul’s beginnings, and notorious visitors such as John Dillinger, Machine Gun Kelly, and members of the Barker Gang. The point is not to treat these people as heroes. It is to show how St. Paul became part of a larger web of crime and political influence.

Meeting the guide outside Cossetta’s

Your starting point is outside Cossetta’s restaurant. The instructions are specific: meet the guide in blue and do not go inside the restaurant. That small detail matters, since Cossetta’s is a busy and well-known place, and looking for a group indoors could waste the first few minutes.

The tour is conducted in English, and you should arrive with a passport or ID card. Since this is a bar crawl for adults, proof of age is important even if you appear well over 21. Bring cash as well, since it is listed among the recommended items and may be useful for extra purchases or tips.

This is a walking tour, so wear shoes that can handle three hours on city sidewalks. The schedule is usually in the afternoon, which gives you a useful option if you want to leave your evening open for dinner or another activity.

The group moves with a live guide rather than an audio recording. That makes the quality of the guide important. Camille has been praised for her grasp of St. Paul’s past and its local bars. Dan has been described as friendly and especially good at shaping the tour around a participant’s interests. Collin has also led the route with an easygoing style.

Following bootleggers through downtown bars

The first stretch introduces the basic character of the tour: St. Paul as a place where criminals could hide, negotiate, and keep moving. Your guide explains how bootleggers and gangsters used local establishments, and how the city’s connections with Chicago brought trouble across state lines.

The bar stops are not just places to get a drink. Each one is meant to carry a story, though the precise sequence is not fixed in the information provided. You can expect the guide to connect the building, neighborhood, or bar culture with the people who once operated in the city’s shadows.

This is where the tour’s format works best. A conventional history walk might point out a building and give you a date. Here, the same setting becomes part of a story about illicit liquor, deals made behind closed doors, or a wanted criminal finding temporary cover. You get a drink, but the drink is really the prop that helps the past feel close at hand.

At the same time, you should keep your expectations in check. This is not a museum tour with preserved crime scenes or a detailed architectural survey. The attraction is the guide’s interpretation and the atmosphere of the stops. If you need every claim backed by a plaque or archive display, this may feel informal.

Meeting the names behind the stories

The tour’s headline figures provide plenty of hooks. John Dillinger is linked to St. Paul hideouts, while Machine Gun Kelly and the Barker Gang are part of the city’s criminal connections. Your guide also discusses Chicago criminals who used underground tunnel systems to avoid the law.

These stories help explain why St. Paul became useful to people who needed a place to disappear for a while. You are not simply hearing a list of famous names. The larger idea is that criminals depended on practical networks: safe places, friendly contacts, compromised officials, and routes that made pursuit harder.

The stories about corrupt officials and unofficial arrangements add another layer. Crime did not operate in isolation. The tour looks at the connection between the underworld and the people who had influence over policing, permits, money, or local decisions. That makes the experience more than a collection of gangster anecdotes.

I especially like that the tour includes less famous material alongside the recognizable names. Dillinger may draw attention, but accounts of local power, neighborhood legends, and quiet deals often tell you more about how a city functioned. Ask questions if a particular period or person interests you. Dan’s ability to tailor the discussion suggests that the tour can become more useful when you take an active role.

Bars, breweries, and the included drink

The $79 price includes one complimentary drink along the route. The tour also visits historic bars and St. Paul breweries, with craft cocktails and premium beers available for purchase. Additional drinks are not included, so budget carefully if you plan to sample several places.

Waldmann Brewery has been singled out as an especially appealing stop. It offers a setting where the drink and the historical mood can work together, and it gives the crawl a change of pace from downtown bar interiors. The experience is not limited to one kind of drinking venue, which helps keep three hours from feeling repetitive.

You may also want to ask about Schmidt Brewery. It is no longer active as a brewery, but the building contains bars and has a connection to the area’s past. The exact inclusion of this stop is not guaranteed, so treat it as a possible suggestion rather than part of the promised route. If the building is open and your schedule allows, it could add useful context about St. Paul’s brewing history.

The drink itself is only part of the value. At a typical bar crawl, the cost can rise quickly if every stop requires a purchase. Here, you receive one drink, then choose how much more to spend. That lets you keep the total under control, though $79 still makes the tour a better fit for someone who values the guide and the stories rather than someone looking for a cheap night out.

You should also pace yourself. Three hours of walking and drinking is more enjoyable when you treat the alcohol as a sample of the setting, not the main event. The tour is about what the bars reveal, not how many drinks you can fit into an afternoon.

The tunnels and the city beneath the surface

The underground tunnel stories give the crawl its most theatrical subject. Your guide discusses routes used by Chicago criminals to evade the law, adding a sense of concealment to the streets above.

Do not book this expecting a guaranteed underground expedition. The information promises stories about tunnel systems, not entry into a tunnel network. That distinction is important. The value is in learning how hidden routes fit into the criminal world, not necessarily in walking through one.

Still, this part gives the tour a strong visual idea. You can imagine people moving through spaces that were difficult for authorities to monitor, using the city’s older structures and connections to stay ahead of the law. It also reinforces the central theme: St. Paul’s history is not always visible from the sidewalk.

For me, the best version of this segment is one that connects the tunnels to the people and institutions around them. Who knew about them? Who benefited? Who chose not to ask questions? Those are the questions that turn a spooky anecdote into a better history lesson.

How much walking and social time to expect

The activity lasts three hours and takes place on foot through historic downtown districts. The route includes several bar stops, so you should expect a mix of walking, standing, listening, and social time.

The pace should suit most people who are comfortable walking around a city for an afternoon. Wheelchair access is listed, which is helpful, though the practical ease of each bar entrance, sidewalk, and interior can vary. If you use a wheelchair, confirm current route details before booking so you know how the individual venues handle access.

The experience works best for people who enjoy small-group conversation and do not mind sharing a bar setting with other adults. It is not designed for children, nondrinkers looking for a quiet historical lecture, or anyone who wants a private vehicle between stops.

The afternoon timing is convenient. You can use the crawl as an introduction to downtown St. Paul, then decide which area or bar deserves a return visit later. It also avoids turning the entire evening into a planned event.

Is $79 a fair price?

At $79 per person, this is not a bargain bar crawl. The price needs to cover more than the drink, since you are paying for a live guide, access to several historic bars, the research behind the stories, and the structure of a three-hour walking route.

I would consider it fair if you care about local history and want a guide to connect scattered places into one narrative. It is less appealing if you plan to visit bars on your own and do not care who used them decades ago.

The price also makes the included drink important, but not decisive. If you buy two or three additional drinks, your total cost rises. If you stick with the included drink and perhaps one extra purchase, the price stays more predictable.

The strongest value comes from the guide. Camille, Dan, and Collin have each been praised for bringing personality and local detail to the route, with Dan especially suited to people who want the discussion shaped around their interests. Since the exact stop order is not fully fixed, the guide’s ability to adjust the experience matters.

Who should book this St. Paul crawl?

I would recommend this tour to adults who like unusual city history, organized bar hopping, and stories about the less respectable side of civic life. It suits a first visit to St. Paul when you want something more distinctive than a standard downtown walk.

It is also a good choice for people who enjoy asking questions. Bring up a particular gangster, brewery, neighborhood, or period, and the conversation may become more personal and useful. The tour is not just a script delivered at fixed points.

You may want to skip it if you dislike alcohol-centered settings, need a tightly specified list of stops, or expect to explore the tunnels themselves. It is also a poor match for anyone under 21, since no minors are permitted.

Free cancellation is available up to 24 hours before the activity, and you can reserve now and pay later. Those policies make it easier to fit the crawl into a changing St. Paul schedule, but they do not change the main decision: are the stories worth the $79 price to you?

Should you book it?

Book the St. Paul Secret Stories Bar Crawl if you want a social afternoon built around bootleggers, gangsters, tunnels, old bars, and local political corruption. The strongest reasons are the live guides, the unusual subject matter, and stops such as Waldmann Brewery that give the history a physical setting.

Skip it if you want a cheap drink tour or a guaranteed underground adventure. For the best value, bring identification, wear comfortable shoes, keep extra drink spending modest, and tell your guide what part of St. Paul’s past interests you most.

FAQ

Where does the St. Paul Secret Stories Bar Crawl meet?

Meet your guide in blue outside Cossetta’s restaurant. Do not go inside the restaurant to find the group.

How long does the tour last?

The bar crawl lasts three hours and is usually offered in the afternoon.

How much does the experience cost?

The listed price is $79 per person.

Is a drink included?

Yes. One complimentary drink is included during the route. Additional drinks are available for purchase and cost extra.

What language is the tour conducted in?

The tour is conducted in English with a live guide.

Can people under 21 join?

No. The experience is not suitable for anyone under 21.

What should I bring?

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