Explore Oak Park and Beyond

Oak Park has always felt like an extension of the city to me. It was the first place I lived after moving to the Chicago area, and I loved my time there. My first apartment was filled with thrifted finds from the Brown Elephant in the Arts District. I’d start mornings at Buzz Cafe, then spend afternoons wandering the neighborhood, ducking into galleries and exploring the tree-lined streets. At the time, I never stopped to think about why Oak Park felt so different from Austin, just a few blocks away, or what history had shaped those differences.

Not long after, I moved to Uptown, but Oak Park remained part of my routine. I’d meet friends for a meal, make the occasional trip back to Buzz Cafe, and, more often than not, stop by the Brown Elephant to see what treasures had arrived since my last visit.

When Dario and I started 77 Flavors, I knew we’d eventually return to tell Oak Park’s story. While researching and recording our Austin episode, we naturally found ourselves crossing into Oak Park. History doesn’t stop at municipal borders, and neither did our curiosity.

This week, I learned even more about the fascinating relationship between Oak Park, Austin, Berwyn, Cicero Township, and the city of Chicago. Oak Park is, in many ways, a community defined by its desire for independence, and that history has shaped everything from its borders to its identity.

To better understand that story, we sat down with Frank Lipo, executive director of the Oak Park River Forest Museum since 1993. What was supposed to be an interview turned into a two-hour conversation that easily could have lasted another three. I always leave conversations like that energized. There’s something contagious about talking with someone whose passion runs so deep. Frank’s enthusiasm was impossible to miss, and it made me even more excited to dig into Oak Park’s history.

Before we sat down, Frank walked us through the museum, pointing out details that most visitors would probably walk right past. One of my favorites was the original wooden floors beneath our feet, preserved from when the building served as Firehouse No. 2 for Cicero Township. Moments like that are a reminder that history isn’t just something you read about. Sometimes you’re standing on it.

The space, currently going through a renovation, houses so many stories, from famous Oak Parkers to the inspiring history of fair housing. Cases line the main floor with books and artifacts from not too far in the past. One of my personal favorites showcased cookbooks that once belonged to different members of the local church. You often find that these cookbooks hold some stories of traditions that are otherwise forgotten.  

It’s easy to admire a place for its architecture, restaurants, or charming streets, but those things only tell part of the story. Every neighborhood has layers that reveal themselves only when you ask questions, listen to the people who have dedicated their lives to preserving its history, and take the time to look a little closer.

Oak Park may have spent much of its history defining itself apart from Chicago, but its story is inseparable from the city’s. Its relationship with Austin, Cicero Township, Berwyn, and the broader region reminds us that borders may appear fixed on a map, but history is never confined by them. Communities shape one another in ways that aren’t always obvious until you begin peeling back the layers.

For me, Oak Park will always be the place where I furnished my first apartment, spent lazy Saturday mornings, and unknowingly began building a relationship with Chicago’s history. Now, every time I walk those same streets, I see something different. I don’t just see beautiful homes or my favorite thrift store. I see a place that has spent more than a century defining who it is, preserving where it came from, and reminding all of us that every neighborhood, no matter how familiar it feels, still has stories waiting to be discovered.

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