You’re probably thinking about Minneapolis right now. It’s okay. Most people do. When someone mentions the Twin Cities, the mind usually drifts toward the glass skyscrapers of downtown Minneapolis or the sprawling chaos of the Mall of America. But honestly? That’s a mistake. St. Paul is the quiet, slightly older sibling that actually holds all the cool stories.
It’s gritty. It’s Victorian. It’s surprisingly deep.
If you’ve ever stood on the High Bridge and looked down at the Mississippi River, you realize this isn't just another Midwestern town. St. Paul Minnesota is a place defined by its hills, its history of gangsters, and a certain stubbornness that keeps it from ever wanting to be like its neighbor across the river. It’s the state capital, sure, but it feels more like a collection of European-style neighborhoods than a frantic American metropolis.
Let's get into what makes this place tick.
The Gangster Paradise of the 1930s
Here is something wild: back in the day, if you were a high-profile criminal, St. Paul was basically your safe house. This wasn’t some accident or a lapse in security. It was a literal business arrangement.
Under the "Layover Agreement" established by Police Chief John O’Connor, criminals were allowed to stay in the city as long as they promised to play nice. They had to check in, pay a small "fee" to the police, and most importantly, they couldn't commit any crimes within the city limits.
John Dillinger loved it here. Baby Face Nelson spent time in these streets.
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You can still visit the Landmark Center today—it’s that massive, castle-looking building downtown. Back then, it was a federal courthouse where some of these guys finally met their match. But for years, the city was a weird, peaceful neutral zone for the nation’s most wanted. It’s a bizarre chapter of American history that explains why the city has so many hidden tunnels and secret rooms in its older basements.
A Mountain of Dead Pigs?
The name "St. Paul" sounds very dignified and holy. It wasn't always that way.
The city’s original name was actually Pig’s Eye. Seriously. It was named after Pierre "Pig's Eye" Parrant, a bootlegger with a messed-up eye who opened a tavern near the river. He was the first person to really set up shop in what would become the downtown area.
Thankfully, a Catholic priest named Father Lucien Galtier arrived in 1841 and built a small log chapel dedicated to Saint Paul. He basically looked around and said, "We are not calling this place Pig's Eye," and convinced everyone to adopt the name of his chapel instead. St. Paul was born. Parrant got kicked out, but his nickname lives on in the local Pig's Eye Lake.
The Summit Avenue Time Machine
If you like architecture, Summit Avenue is your holy grail.
It is the longest stretch of Victorian-era homes in the entire country. We’re talking 4.5 miles of massive, limestone mansions that look like they belong in a period drama. You’ve got the James J. Hill House—a 36,000-square-foot beast of a home—sitting right next to the Cathedral of St. Paul.
F. Scott Fitzgerald, the guy who wrote The Great Gatsby, lived here too. He actually wrote his first novel, This Side of Paradise, while staying at 599 Summit Avenue. He had a complicated relationship with the city. He once called it a "museum of American life," which is honestly a pretty accurate description of how it feels to walk that street in the fall.
Why the Streets Make No Sense
If you’ve ever tried to drive in St. Paul, you’ve probably ended up screaming at your GPS. It’s a nightmare.
Unlike Minneapolis, which is laid out on a very logical, easy-to-follow grid, St. Paul’s streets look like someone dropped a bowl of cooked spaghetti on a map. There’s a legend that the streets were paved over old cow paths. That’s probably not true, but it feels true.
The real reason is the geography. St. Paul is built on a series of bluffs and plateaus. The roads had to follow the natural curves of the river and the steep hills. Combine that with the fact that different neighborhoods were plotted by different developers at different times, and you get a city where streets change names for no reason and intersections happen at 45-degree angles.
The Winter Carnival Was Born Out of Spite
In 1885, a reporter from New York visited the city and wrote that St. Paul was "another Siberia, unfit for human habitation."
The locals didn't get offended. They got petty.
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To prove that they loved the cold, they launched the St. Paul Winter Carnival in 1886. They built a massive ice palace, held parades, and created an entire mythology involving Boreas (the King of the Winds) and Vulcanus (the Fire King). They’ve been doing it ever since. It is the oldest winter festival in the United States. While everyone else is huddling inside, people in St. Paul are out carving ice blocks and running races in sub-zero temperatures. It’s a level of stubbornness you have to respect.
The World's Largest Hockey Hair Population
Okay, maybe that’s not an official census stat, but St. Paul is the capital of American hockey.
The Xcel Energy Center is where the Minnesota Wild play, but the real heart of the sport is the Minnesota State High School Hockey Tournament. It’s held in St. Paul every year, and it’s a massive deal. It sells out the arena. It’s televised. And yes, "hockey hair" (the glorious flow coming out of the back of the helmet) is celebrated with almost religious fervor.
Underground Secrets
Below the city streets, there is a literal labyrinth.
The Wabasha Street Caves are the most famous part of this. They are man-made caves carved into the soft sandstone bluffs. Over the decades, they’ve been used for:
- Growing mushrooms (the humid, dark environment was perfect).
- Storing root vegetables.
- Operating a speakeasy during Prohibition called "Castle Royal."
Legend has it that several mobsters were murdered in these caves, and if you believe the ghost tours, they never left. Whether or not it's haunted, standing inside those sandstone walls gives you a physical sense of the city’s layers.
The Rice Park Connection
Rice Park in downtown St. Paul is older than Central Park in New York.
It’s a tiny, elegant square surrounded by the Landmark Center, the Ordway Center for the Performing Arts, and the St. Paul Central Library. It feels incredibly European. During the holidays, they string up thousands of lights, and it looks like a scene from a Hallmark movie.
What people often miss are the bronze statues scattered around. You’ll find characters from Peanuts here. Why? Because Charles Schulz, the creator of Snoopy and Charlie Brown, was born in St. Paul. He grew up here, and the city is peppered with tributes to his work.
A City of Neighborhoods
St. Paul doesn't have a "cool" district because every pocket of the city thinks it’s the best.
- Lowertown: The old warehouse district turned artist loft heaven. It’s where you’ll find the best farmers' market and CHS Field, where the St. Paul Saints play.
- Grand Avenue: The place to go for boutique shopping and eating your weight in ice cream.
- Frogtown: Historically a working-class hub with some of the best Hmong food you will ever eat in your life.
- West 7th: A gritty, fun stretch of bars and restaurants that leads right to the hockey arena.
The Hmong community in St. Paul is one of the largest in the world outside of Asia. The Hmong Village and Hmong Town Marketplace aren't just shopping centers; they are massive cultural hubs where you can find everything from traditional medicine to incredible papaya salad.
The Great River Passage
Most people forget that St. Paul has more riverfront than any other city along the Mississippi.
The city is currently working on the Great River Passage, a project to better connect the urban areas with the 26 miles of riverfront. It’s a massive natural asset that for a long time was hidden behind industrial zones and train tracks. Now, it’s becoming the city’s backyard. You can kayak right past the downtown skyline or bike for miles along the Sam Morgan Trail.
What to do next
If you're actually planning to visit or just want to dig deeper into the weirdness of this city, don't just stick to the tourist traps.
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- Go to a St. Paul Saints game. They are a minor league team (owned in part by Bill Murray), and the atmosphere is way more fun than a standard MLB game. There’s a pig that brings out baseballs.
- Walk the Skyway. St. Paul has a massive system of indoor bridges connecting the buildings downtown. It's a weird, liminal space that feels like a sci-fi movie when it's empty on a Sunday.
- Eat at Mickey’s Diner. It’s a classic railcar diner that’s been in a bunch of movies (The Mighty Ducks, for one). It’s greasy, it’s loud, and it’s open 24/7.
St. Paul isn't trying to impress you. It’s just being itself. That’s probably the most important fact of all. It’s a city that values its history, its quiet neighborhoods, and its ability to survive a blizzard without complaining. Well, maybe a little complaining. But only over a beer at a local dive bar.