Did You Know?

While the Chicago region’s population grew by 18 percent since 1980, the traffic increased by 66 percent in the same period.

Bike tours fueled by love for local history and cycling

In 2008 Lee Diamond, owner of Big Shoulders Realty, decided to combine his passions for bike riding and Chicago architecture by scheduling bike tours of different areas of Chicago. Since then Diamond has scheduled tours twice each month in the spring, summer and fall and once each month in the winter.

During the tours, Diamond leads people biking on a 12- to 18-mile route through a different Chicago neighborhood, making frequent stops to point out and elaborate on landmark homes, churches, schools, parks and businesses — each with its own place and time in architectural history. The tour registration fee is usually $10, but he frequently offers research, pre-event and photo tour rides that are free. 


Diamond (pictured above) has many goals for the rides. “I would like to get people on their bikes,” he says. “I would like to get people to learn about their city and their past and develop an appreciation for what we have here. I would like to see people turn appreciation into preserving their properties, caring about old properties, advocating for historic preservation.”

Diamond has established a repeating series of tours and often refreshes the list by adding new areas. Neighborhoods covered include Logan Square, Humboldt Park, Austin, East and West Garfield Park, West Town, Bridgeport, Hyde Park, and Lincoln Square to name a few. The tours are well-organized and full of nuggets of historical information on a variety of buildings one might not notice whiling driving past in a car.

Rolling through history
Our springtime tour of Norwood Park began at the park itself, located at 5801 N. Natoma Ave. Diamond gave each of us a map outlining our route through the neighborhood. On the other side of the map was a cue sheet for the route with turn-by-turn directions. Being a terrible map-reader, I appreciated this route sheet. Diamond also gave us a comprehensive list of the neighborhood’s architectural highlights and their street addresses.

After a visit to Taft High School, we pedaled through a few peaceful residential streets to the Noble-Seymour-Crippen House at 5624 N. Newark Ave. (pictured below). The south wing of the house, built in 1833, is believed to be the city’s oldest surviving building. Today this impressive mansion is the home of the Norwood Park Historical Society. It’s a registered Chicago Landmark and is listed with the National Register of Historic places.


The Norwood Park tour took about 3 hours and contained many other points of architectural interest. Among them was the Wingert House at 6231 N. Canfield Ave. — one of the oldest surviving farmhouses in the city and also a Chicago Landmark. Diamond also led us to several area churches, parks and schools, as well as the Danish Old People’s Home at 5656 N. Newcastle Ave., a large stately brick edifice that is still in operation today.

By the end of the tour we were back where we had begun, at the park adjacent to Taft High School. The tour was enjoyable. I liked the combination of easy bike riding and the casual absorption of historical facts.

Some of the Norwood Park tour participants were repeat customers and have ridden in many of Diamond’s tours over the years. Eve Jennings has been a loyal tour participant since 2011. When asked what keeps bringing her back, Eve said, “My mom was the one who first heard about the bike tours and we have done them together as a way to spend time together that is interesting and active. My sisters have also joined in on a few rides.”

Finding the hidden riches
Through Chicago Neighborhood Bicycle Tours, Diamond has created a unique legacy for the city he loves. He has researched, documented and photographed the architectural history of many of Chicago’s key neighborhoods. It’s his ongoing quest to learn more of its forgotten history and hidden riches. He shares this information on his website, The site features photographs of many little-known historical buildings, neighborhood site maps and tour registration information. The site also contains spectacular posters, a unique design for each different tour created by Diamond’s longtime friend, artist Ross Felton.


Owning and operating his own realty company has to keep Diamond busy enough. So what does he get out of the additional time and energy spent on planning and conducting weekend bicycle tours throughout the year?

Diamond said part of the reason he keeps doing the tours is that he loves the historic research and the photography. “I get to learn in much greater depth than I otherwise would, details of our amazing city,” he said. “Basically I get to learn lots of great information and geek out on architecture and bicycling, which are two of my passions.”

Saturday, Aug. 17, is a tour of Jefferson Park. Check out other upcoming tours here.

Lynda Barckert, an Active Trans vounteer writer, contributed this blog post and the photos.