Midnight riders: Annual history tour takes Loyola students across Chicago by bike

Loyola University Chicago President Mark C. Reed pulled an all-nighter on Thursday.

He wasn’t in his office. Instead, he spent the night getting a crash course in Chicago history—cycling more than 30 miles across Chicago alongside more than 220 students, staff, and faculty during this year’s Midnight Bike Ride. Begun in 1989 by Loyola history professor Timothy Gilfoyle, the annual tradition takes riders on a curated tour of dozens of historic and architectural landmarks across the city.

“I had it on my ‘bucket list’ of things to experience at Loyola,” Reed said. “Seeing our professors sharing their knowledge and passion with students is one of the greatest privileges of my job.”

The ride began at 9 p.m., at the plaza just south of the East Quad near Madonna della Strada Chapel. Gilfoyle led the group past century-old Catholic churches; the Green Mill Cocktail Lounge, a popular jazz club and Prohibition-era mainstay of Al Capone and his henchmen; The 606, an elevated bike and pedestrian trail retrofit from a decommissioned rail line; and a nearly deserted stretch of Michigan Avenue that the riders took over in the wee hours.

At each landmark, Gilfoyle, who has written extensively on Chicago’s history and urban development, including the book Millennium Park: Creating a Chicago Landmark, paused to provide a brief window into the site’s historical significance. The tour arrived back at the Lake Shore Campus at 7 a.m., hours after Reed treated roughly 150 riders to breakfast at the Golden Apple Grill & Breakfast House.

“Perhaps the most interesting element of the tour is that students can see physical structures that may be residential today, but were once industrial, and there’s a history there that has been largely forgotten, or is kind of invisible in plain sight,” Gilfoyle said. “You might say that it allows students to better appreciate, experientially, that history is all around them.”

That’s a lesson Gilfoyle first learned as a young PhD student at Columbia University, where he was a regular participant in an analogous historical bike ride through New York led by Kenneth Jackson, the Jacques Barzun Professor Emeritus of History at Columbia University and author of Crabgrass Frontier: The Suburbanization of the United States.

“What attracted me to this field was that cities are very chaotic places,” Gilfoyle said. “And I [had this experience] with Ken Jackson, and it gave me some sense of understanding what was going on around me. The rest, you might say, is history. I became so enraptured with that, that I made it my own life’s work as well. “

Gilfoyle brought the concept to Barnard College and Sarah Lawrence as a visiting professor, and on arriving at Loyola, he reinvented it for Chicago.

“Richard Cobden, the 19th-century writer once said, ’If you visit the United States, there are two things to see: Niagara and Chicago.’ And I think that reflects how Chicago was the shock city of the United States in the 19th century at the height of the so-called Industrial Revolution. And that history is all around us in ways we don’t fully appreciate,” Gilfoyle said. “I often tell my students, without a vivid link to the past, the present is chaos, and the future unreadable.”

Though New York and Chicago are distinct, they have many common traits—a colonial history, an orthogonal street grid, large immigrant populations, and significant industrial economies and service sectors. Seeing how these characteristics are written into the urban fabric, Gilfoyle said, brings the city’s working-class roots to life and helps ground students in Chicago’s rich historical vernacular.

“If you’re in a car or a bus, you’re flying by these sites without really stopping to allow their impact to sink in,” he told me. “On a bike, you have more leeway in terms of stopping and going. So I think it’s a better experience to be able to immerse yourself in the physical environment in ways that go beyond just looking at photographs or watching a video or reading a book.”

Over the years, the tour has had many notable moments—including a police escort of bike riders past throngs of fans leaving a Guns & Roses concert at Wrigley Field and multiple tours of the former site of A. Finkl & Sons Steel Works, Chicago’s last surviving steel mill. As attendance has grown, the route has evolved, but the core message has remained the same: History is legible for those willing to pay attention.

At midnight, Elise Warren (BS ’28) peeled off from the group to return to her apartment and rest up for an early morning class. But before she did, the biochemistry major gazed up at the dusky light coming off the facade of St. Mary’s of the Angels, a Catholic church in Bucktown. She smiled with wonder.

“I think it’s really cool to be able to immerse yourself in the surroundings of where historic events took place and see how that history affects how I’m living today,” she said. “There have just been so many changes that led to how the city looks right now.”

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