Old Town: A Victorian Age of Art, History & Cultural Charm

Posted on October 16, 2015 by Tara Teague

A neighborhood full of life, Old Town, heavily known for its comedic Second City staple, originates as the hippie center of the 1960’s. Lined with Victorian buildings and a heavy storefront variety of bakeries and pubs to boutiques and highly sought after cuisine, the charm of this area has only grown throughout the historical decades. From sprouting townhomes and high-rises, to single-family homes, the streets are lined in grand trees that stand center to the distinguishing architecture that is among some of the only original brick structures to survive the Great Chicago Fire of 1871. In fact, St. Michael’s Church is what many claim to be the border of Old Town. Since Old Town does not — on paper — technically exist, many locals will tell you if you can hear the bells of its beloved church, then you are living within this sought after community.

For the history junkie: Old Town’s name originates from World War II, when a fair titled ‘Old Town Holiday’ became so socially prevalent, the name just stuck. And of course was shortened because even back then it was fashionable.

If Victorian era and old world character is where your rental desire lies, then this antiquity gem is the area to explore. Generally known to be quite the affluent area, affordable rentals may not be as out of reach as you may think. As fate may have it, I uncovered this Two Bedroom property with very little digging, and mostly just a few keyboard presses, and voila! For $725 a person, you can live in the heart of what some claim to be the ‘most pedestrian friendly street’ and a surplus of CTA options outside your front door. It may not be your fortress, but this loft style lay-out with the true charisma in the exposed brick and in-unit laundry? These are the properties that don’t last long on listing pages before someone is laying a ‘Welcome Home’ mat in front of the archway.

The great part about Chicago? Even if you don’t live in the neighborhood you can still easily enjoy it.

Dating back to 1950, the Old Town Art Fair is one of the most seasoned art fairs in America. Drawing in over 250 artists each summer to showcase a melting pot of creativity including, drawing, painting, photography, and hand crafted jewelry. Local bands contribute live performances throughout the day, as well as a historic garden walk and even a children’s area. An inviting fair where everyone is welcome allows the true talent that lies within this city to proudly stand on display.

A SNL comedy nerds dream dating back to the 1960′s, Second City has developed into a comedy empire. Known to be the most significant and creative theater in the world, many famous comedians today got their start within these walls. Seen to some as an unconventional way to approach stand up, sketch and improv, their experimental imagination gained them a reputation of discovering generations of comedic superstars. The debut of Saturday night live, began with three Second City alums, setting the tone for what these four walls were capable of uncovering. The continued creation of innovative media found in television, film and digital dimension, The Second City’s imprint is still felt in today’s entertainment outlet. Think, Mike Myers, Steve Carrell, Stephen Colbert and Tina Fey, who started right here in Old Town Chicago. No gym? No Problem. Get your ab workout at the venue where there is not a bad seat in the house.

Standing as one of Chicago’s oldest neighborhoods, these streets are lined with tales of the past. Where better to unveil these stories than from the long standing pubs that accompany the history — and locals — of Old Town.

Marges Still. Dating back to prohibition, originally known as Marges, this pub knew its audience and ran with the rebellion continuing to serve drinks that weren’t so soft. After many years of fighting to keep this place alive, in 2007 the neighborhood was finally heard. Symbolically the name was changed to Marges Still, as a testimony of its past, present and inevitable local future.

The pubs that remember it all and probably would like to forget some of it (the disco craze I imagine to be one of those visuals you wish partial lobotomies were invented) Twin Anchors, with its famous BBQ ribs and IPA selection, to Old Town Ale House where pulling up a bar stool means unwillingly emerging yourself with some serious Chicago history. The art of political figures in compromising situations (mug shots), to the very real chance that the man sitting next to you drinking the PBR is a surplus of stories ready to tell you what ‘really happened’ in 1964, and if you get him talking, cancel your afternoon plans.

Living among a city like Chicago is like walking through a piece of prominent history. Old Town is just one of those neighborhoods that if you read between the lines, you are sure to find a story that is much more than what meets the eye.

Like what you read? Give Tara Teague a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.