Chicago on Two Wheels: Lakefront Neighborhoods Bike Tour

On a crisp Saturday morning in Chicago, I join a biking tour led by Bobby’s Bike Hike. Having explored the central part of Chicago, I want to see the relatively less explored parts of the city, so I join the Lakeside Neighborhoods Bike Tour.

After some orientation on bike safety and so, I emerge from the entryway of the company’s office in Streeterville along with 16 other cyclists, including York, our bike tour guide. After a few turns, we reach N Fairbanks Ct, a major thoroughfare near Magnificent Mile. But instead of going south back to where we explored on our first morning here, we push on north to the Museum of Contemporary Art in the neighborhood of Streeterville. We mark our first stop here, and York begins his first story about Chicago — specifically about the water tower across the museum. The tower was one of the few structures to survive the Great Chicago Fire in 1871 because it was made of stone and held a large amount of water.

The Lakefront Neighborhoods Bike Tour by Bobby’s Bike Hike Chicago takes guests off the city’s main tourist route and into the quiet streets, parks, and the lakefront in the northern part.
Bike tour guide York shares some stories about Chicago’s Water Tower Place in front of the Museum of Contemporary Art.

From the museum, we push farther north into the Gold Coast, a historic district where leafy streets are lined with high-end residences and establishments. One of these is a condominium that Hefner bought in the 1970s and turned into his personal harem. Hefner eventually moved the mansion to Malibu, where the warmer weather gave his girls the reason to walk around in bikinis. Hefner sold the mansion to a school, which turned the mansion into a boarding house. In turn, the school sold it two years later, and the building was repurposed into a luxury condominium.

Another notable building in the area is the Cardinal Mansion, which serves as the official residence of the archbishop of Chicago. The current bishop, though, having vowed a life of austerity, found the house too fancy and stays in a local rector instead.

The old Playboy mansion is now a high-end condo unit in the Gold Coast, an affluent neighborhood in northern Chicago.
The Cardinal Mansion is the official residence of the archbishop of Chicago.

From Gold Coast, we cruise northward along N State Parkway and reach Lincoln Park, Chicago’s largest park and the centerpiece of its namesake neighborhood. We stop first at the Lincoln Monument, which stands across the lawn from the back of the Chicago History Museum building. York talks something about the area being a previous graveyard for victims of a cholera pandemic, but I don’t hear much as I get distracted with taking pictures of the surroundings.

We then head west to the Old Town, another historic neighborhood in Chicago with some Victorian-era buildings, most notable being the St. Michael Catholic Church. According to York, it’s a hippie community in the 60s. It also saw riots in the 70s and 80s due to tense racial divisions. Right now, though, Old Town has been gradually gentrified.

We pedal our way to Oz Park, so named because of the statues created by artist John Kearney depicting various characters from L. Frank Baum’s The Wizard of Oz. Kearney was approached by an elderly woman and was asked to make sculptures of the characters from the story. The woman didn’t get to see Kearney’s renderings of Dorothy and friends, though, as she died before the project was approved by the city four years later.

The Chicago History Museum stands at the southern end of Lincoln Park.
The St. Michael Catholic Church’s red brick structure towers above Old Town neighborhood.
A statue of Dorothy and Toto stands in front of the Oz Park.

From Oz Park, we bike east to the Lincoln Park again, stopping at the east entrance of the Lincoln Park Zoo for a toilet break. I take this opportunity to see the zoo a bit (the entrance is free), though I get to see the ducks and the flamingos.

After our potty break, we bike further east, crossing a pedestrian bridge to the North Avenue Beach. Lake Michigan here looks like the ocean (albeit without the salty smell), and you forget that Chicago is far from either coast. The beach also connects us to the Lakefront Trail, an 18.5-mile long path shared by cyclists, joggers, skateboarders, and any other people not driving a four-wheel vehicle or a motorcycle.

A flamboyance of flamingos is just one of the many faunas in Lincoln Park Zoo.
North Avenue Beach is one of Chicago’s most popular beaches.
The 18.5-mile long Lakefront Trail was Chicago’s first designated bike path.

We traverse the trail and eventually get back to Streeterville and to the Bobby’s Bike Hike office. The tour left me wanting to explore more of the city by bike, and this cements the idea that, even if only for the biking opportunities, Chicago can really be my adopted home.

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