A Stroll Through Time: Discovering Chicago’s Hidden Layers

As a retired teacher with a penchant for road trips and a love for history, I’ve always been drawn to the stories that lie beneath the surface of the places I visit. My recent adventure in Chicago with Custom Walking Tours was no exception. This time, I was accompanied by my daughter and her friend, and together we embarked on a journey through the city’s rich tapestry of history and flavor.

The Echoes of Beer Barons

Our tour began at the Gurgoyle Fountain, a place that seemed to whisper tales of the past. Originally removed in 1908, the fountain was restored to its former glory in 2002, a testament to Chicago’s dedication to preserving its history. As we stood there, I couldn’t help but think of the countless road trips I took in my youth, each stop a new chapter in the story of America.

We then wandered down Hoyne Avenue’s Beer Baron Row, where grand mansions built by German brewing magnates stood as proud reminders of a bygone era. Our guide, Henry, wove stories of the families and architecture that gave the neighborhood its character. Walking those shaded blocks felt like stepping into another time, much like the small towns I’ve visited across the Midwest, each with its own unique charm and history.

A Journey Along the Bloomingdale Trail

Our path led us to the Bloomingdale Trail, a remarkable elevated greenway that was once a train line. As Henry shared its history and the plans for its future, I was reminded of the scenic routes I’ve traveled, where the journey is as important as the destination. The trail, much like the open road, offers a sense of freedom and possibility.

Our first tavern stop was a Schlitz Brewery tied-house, an architectural gem that brought back memories of the roadside diners and motels I’ve encountered on my travels. The building’s iconic “belted globe” insignia, restored in bright color, stood as a beacon of history and tradition. Hearing Henry describe the intricacies of tied-houses and prohibition policies was like uncovering a hidden layer of the city’s past.

A Toast to Tradition

The Map Room, a bar I hadn’t visited since my Chicago days, was our next stop. Its walls lined with maps and vintage guides, it felt like a home for wayfarers and neighbors alike. Here, Henry introduced us to the legendary “Chicago Handshake”: a shot of Malört with an Old Style chaser. The taste was unexpected, much like the surprises I’ve encountered on the road, each one adding to the rich tapestry of my travels.

As we continued our walk, we passed another tied-house, this one shuttered and painted white, a stark contrast to the vibrant landmark we had admired earlier. It was a reminder of the ever-changing landscape of the places we visit, where history and modernity coexist in a delicate balance.

Our tour concluded back at the green space where we began, with a taste of Cohasset Punch—a bold, sweet concoction that was once a beloved local cocktail. Sipping it was like tasting a piece of vintage Chicago, a fitting end to a journey through the city’s hidden layers.

Henry’s storytelling was warm and detailed, his knowledge deep, and his passion contagious. This tour was a reminder of why I love to travel: to uncover the stories that lie beneath the surface, to connect with the past, and to savor the flavors that make each place unique. If you’re ever in Chicago, I highly recommend taking a Custom Walking Tours with Henry. It’s an experience that will leave you with a deeper appreciation for the city and its history.