Cobb Gate at University of Chicago Campus

When we say "57th Street" in Chicago, the person in-the-know can tell you that this is 57 blocks south of Madison Street and we add a cardinal direction (East) we know that we are east of State Street, that Great Street. I first found this corner of 57th Street — this curious mile long stretch from Stony Island to Cottage Grove Avenue — when I was just 18 and new to Chicago.

It was just another tiny bit of the grid that aggressively defines the City of Wind, from Rogers Park all the way down to the southwest corner that is Clearing. Come walk with me as I tell you about a trio of sites along this street in the vibrant Hyde Park neighborhood that are well worth your time.


STOP 1: Cobb Gate, You Are Grotesque

Cobb Gate at University of Chicago

On an orientation tour with several other dozen precocious youth attending college at the University of Chicago, I looked up and found myself surrounded by grotesques. These fanciful creatures are not to be confused with gargoyles, which have spouts to dispense water on unsuspecting passers-by.

I remember being tired, exhausted and wondering: "Will this gate provide me with a bit of shelter on a snowy Chicago day?" Over my time as a student, it certainly did. Curiously enough, it took me a few years to learn that these carved creations were meant to represent the path of a student as they made their way through the college experience.

Not surprisingly, the creation at the top of the Cobb Gate (1027 E. 57th Street) represents the triumphant graduating senior. Where are they off to, you ask? Law school, academia, the financial sector, and any other number of professionals profound and some much less so.

Slow down and make sure and take in all of its rich details. If you wait more than a few minutes, you'll be joined by others peering up, up and away.


STOP 2: A Bibliophile's Delight: 57th Street Books 

57th Street Books Chicago

The walk east from Cobb Gate to 57th Street Books (1301 E. 57th Street) features Collegiate Gothic edifices, modest frame houses made immodest by their surrounding palatial structures, and academics hurrying back and forth. 

You must step low to enter this fine repository of books, magazines, notecards, newspapers, and other printed materials, so watch your head. As this more playful cousin of the nearby Seminary Coop Bookstore, their offerings are a bit more accessible to the general public, yet still erudite. 

I’ve always loved their Chicago section, as the staff carefully curates the offerings here and you will leave with more than you planned to purchase. It’s the way of any good bookstore. Make sure and ferret your way to the back of the store to take a look at their books on geography and other aspects of terra firma.


STOP 3: An Italian Royal Family (With Pizza)

Medici Restaurant Chicago

As I wandered one night during my first weeks of college, I encountered a Renaissance referent in the form of a two-story restaurant tucked next to a bank and an upscale grocery for the locally affluent. It was, and is, the Medici on 57th Street (1327 E. 57th Street). 

Walking in, you’ll notice a series of wood booths surrounding a series of modest tables, all of which are covered with carvings dedicated to romances long ago, some recent memories, and just folks passing by. It’s an informal Hyde Park tradition to add a bit of carving, so why not partake?

As far as the food goes, I can recommend the thin crust pizzas without reservation. The garbage pizza has sausage, ground beef, pepperoni and a diverse set of vegetables that make for a meal for now and later. There are other less meaty options, and on the green side, might I also suggest the Ensalata Kimba? It has granny smith apples, red peppers, bleu cheese, pecans, and croutons served over romaine lettuce. 

I’ll leave you with this additional tip for Medici: you’re also allowed to bring your own alcohol, so make a stop before coming on in to enjoy a spirituous beverage with your meal. 


This is part of an ongoing series exploring Chicago from A to Z, highlighting a unique place for each letter of the alphabet. Stay tuned for more entries!  

Additional image credits: The University of Chicago, Seminary Coop, and Medici Restaurant