Until three months ago, I lived in Saint Louis. I was there for five and a half years, and I loved it, even in the summer when the temperature reached 108 degrees, but I could never, in good conscience, call myself a Saint Louisan. You can't be a Saint Louisan unless you went to high school there. In Saint Louis, the high school you attended is an indelible mark that carries important information about your religion, social class, and salient personality traits. You can't even pick a random high school and pretend you went there. Saint Louisans have an elaborate social network comprised of cousins and old, old friends which allows them to identify outsiders easily.
Nonetheless, during my time there, I adopted some Saint Louis habits of mind. These were mostly a mixture of defensiveness and a sense of deep underappreciation. I laughed scornfully when I visited friends in Brooklyn and saw the sign that said, "Welcome to Brooklyn, Believe the Hype," but I was thrilled when those same Brooklyn friends came to visit me and said they never realized Saint Louis was so cool.
It was pathetic, I realize. Saint Louis should not require so much validation from outsiders. In terms of the amenities of a big city, it can't compete with Chicago (the lack of an Ikea is an ongoing source of bitterness). But if you live in Chicago, why would you want to travel five hours just to see another Chicago, albeit one with cheaper beer? Saint Louis should be appreciated on its own terms.
It's better to drive there. Saint Louis does have public transportation, but it's not very quick or convenient. If you bring along a traveling companion, the trip will cost you one tank of gas each, less than an Amtrak ticket and probably Megabus, too. And the price of gas in Missouri will surprise and delight you.
When you reach Springfield, turn your car radio to 88.1. That's KDHX, Saint Louis's community radio station. If you hate what's playing, try again later: the format changes every couple of hours, and it's run by volunteers with very deep record collections. There are almost no commercials. It's about as perfect as radio gets. It will also ease the pain of the last 100 miles on I-55, possibly the most boring stretch of highway in America.
But that also means you'll be even more grateful once you finally reach Saint Louis. If you can, time your arrival into town to coincide with sunset. The Gateway Arch always looks spectacular, but that's when it becomes magical. (The Arch, by the way, is best appreciated from the ground. The trip to the top is overpriced, boring, and induces claustrophobia.)
Don't stay downtown unless you plan to spend your weekend attending Cardinals games and getting shitfaced. Saint Louis's greatest charms can be found in its outlying neighborhoods with their picturesque old-fashioned brick houses and tree-lined streets. Check into the Moonrise Hotel in the Delmar Loop or, if you're feeling wealthy, the Chase Park Plaza in the Central West End. The Moonrise is kitschy in the best possible way, decorated with space memorabilia, topped by the world's largest revolving model of the moon (yes, it's true!) and a roof bar with a great view and a sound system that plays only songs with the word "moon" in the title. The Chase is just classy. And it has a pool.
Once you're settled, make your way to the Royale on South Kingshighway. Barkeep Steve Smith is a former Chicagoan, born, raised, and high-schooled, and he loves his adopted city as only a transplant can. Let him fill you in on its colorful history and introduce you to its wide variety of locally brewed beer, which of course he keeps on tap. Be amazed at how far Saint Louis has moved on from Budweiser. Then grab a table on the patio and flip through the weekly Riverfront Times for recommendations on where to eat and other ways to amuse yourself while you're in town. (That's my former employer, by the way. I'll vouch for its trustworthiness.)
There are two things you should definitely not miss. The first is the Soulard Farmers' Market in the city's oldest and most haunted neighborhood. Its management claims it's been open since 1779. The produce there is sometimes dubious, but that's not why you go. You go for the live chickens, the squirrel and gator meat in the butcher shop, the knockoff designer sunglasses, the freshly made miniature doughnuts, and some of the best people watching in the whole city.
The second thing is the City Museum in the Washington Avenue Loft District. Don't be put off by the name. It's not a museum, per se, more like a gigantic art installation where everyone is encouraged to touch, crawl, climb, swing, jump, slide, run, and scream as much as they want. There's a network of tunnels to explore. There's Monstrocity, an enormous jungle gym constructed of pieces of salvage from around the city, including airplane fuselages and a fire truck. There's a working shoelace machine, in honor of the building's prior incarnation as the International Shoe Factory. There's a six-story tornado slide. There's a Wurlitzer organ. There's a carnival midway with a display of corn dogs through the ages. There's a circus. If we had a City Museum here in Chicago, we'd never shut up about it.
Saint Louisans, though, only become obnoxious braggarts when the subject of their baseball team comes up. Even the most devout Cubs fan must admit it's a good one. (Yes, I was there when they won the World Series in 2011 and, yes, I cheered like a lunatic.) Catch a game, if you can, and swelter in the heat like real Saint Louisans do. If you wear Cubs paraphernalia to Busch Stadium, Cards fans won't even heckle. They'll just laugh at you in a gently condescending way. Sort of like the way Chicagoans laugh at Saint Louis.