The Chainlink

Chainlink Rider Profile: Lee Diamond

Among the most uniquely "Chicago" bike rides featured in The Chainlink's event calendar are Lee Diamond's architectural tours.

Diamond is not only an avid cyclist and cycling advocate, but a professional realtor (with a specific interest in historic preservation), as well as the son of man who was heavily involved in the Cleveland Historical Society.

These attributes make Diamond uniquely equipped to acquaint even longtime residents to a side of our city they never knew existed. And the fact that you're seeing Chicago on two wheels makes the experience that much more enjoyable.

Tour of Uptown and Andersonville. Photo by Aaron Bussey.

The Chainlink recently caught up with Diamond to learn more about his interest in bikes, as well as highlight five rides that Lee is hosting throughout the summer and fall.

CL: How did you get started riding?

LD: Just following the older kids on my little red Schwinn around the neighborhood.

CL: What inspires you to get on your bike?

LD: Different things. I ride for work, pleasure, exercise, mental health and social interaction so any opportunity to ride where good weather, some free time and proper tire pressure align, I am already ready to go! A timely invitation to go on a decent ride with good company is irresistible.

CL: Favorite famous cyclist and why?

LD: (Eddy) Merckx of course, but growing up, it was all about Greg Lemond. I raced as a junior when he was a new pro rider and I read all the magazines and really thought it was incredible for an American rider to be contesting and winning races with all of those Euro pros.

CL: Any advice for bike newbs?

LD: Riding is about balance. The key to balance is in not thinking too hard about balancing. Relax, and you’ll do fine. 

CL: Zen biking - What’s your secret spot you like to bike to?

LD: It’s hardly any secret but my favorite route is from Evanston past the Skokie Lagoons, into Glencoe, a stop at the Botanic Gardens, and back through the North Branch Trail to Milwaukee and then my office.  Best conceivable way to start the work day and achieve mental peace and preparedness.

CL: Where do you dream of biking (that you haven’t yet tried)?

LD: Italy. I was there when I was young and that is where my mom is from so I would love to go back and bring a road bike with me or rent a nice one while I was there.

CL: Top five places to bike to for a snack, drinks, coffee, or food (please include location)?

LD: Five huh?  OK, here it goes:

  • Arriva Dolce – 1823 St Johns Ave, Highland Park, IL 60035

If going on a northern bound training or rigorous ride, I would either stop here and get espresso and head back, or stop here after hitting Fort Sheridan or University Hill or the Old School routes that we like and lots of other roadies and rouleurs hit on the Northshore.  Their gelato is excellent and if you get there early enough, the apricot scones will do you right.

  • Jamba Juice - 1849 Green Bay Rd, Highland Park, IL 60035

Yes, a corporate chain, but it is hard to mess up a smoothie and they do the opposite of messing them up. You can get them with all fruit and you can certainly find a combination that fits your tastes, especially since they will make all of their new AND old recipes, even if it isn’t on the menu.  If we ride light or don’t have much time, we stop at Arriva Dolce, but if we ride hard, then you hit the smoothie shop.

  • Farmhouse - 703 Church St, Evanston, IL 60201

I never thought I would leave the city, but we moved to Evanston in 2009 so our son could attend a special needs public school called Park School.  Evanston is pretty easy to get used to and love and there are lots of great places to explore, shop, relax, recreate, etc., but the downtown area has a lot of options.  This place is right near all of it and by the main library and has a farm to table practice with great food and drink with lots of bike parking in the area, and plenty to explore after you eat.

  • A&G Fresh Market – 5630 W Belmont, Chicago, IL 60634

Our office is in Jefferson Park, just north of Portage Park so I still make it over to A&G a few times each season, but when we used to live just two blocks from the best produce, nuts, and imported candies and treats you have ever seen.  They aren’t the place to necessarily shop for staples, but for the aforementioned, there is no better.

  • Quesadilla La Reyna del Sur - 2235 N Western Ave, Chicago, IL 60647 or 1418 Howard St, Chicago, IL 60626

Whether you find yourself near Rogers Park on the far northeast side of the city or near their original Bucktown spot, this is an outstanding all vegetarian Taqueria with authentic flavors and all types of varieties of meatless options and delicious fresh juices and smoothies.  Even my meat eating friends are amazed.

South Loop Tour. Photo by Andy Ross.

CL: Could you please tell us about the upcoming rides you've organized?

LD: I have been organizing rides of Chicago neighborhoods for almost 10 years now. The demands of our work, family and caregiving schedules have changed how I am able to do these rides in the last few years, so they are fewer, further between then they used to be, but I still like to do them. I put all of the information up on our website Chicago Velo and people can sign up for our newsletter, read our blog or register for our rides. This summer and fall we will be doing rides featuring the northern most Community Areas of Chicago which are all along what is known as the Indian Boundary Line.  The boundary line is a vestige of the Treaty of St. Louis of 1816 and this is the 200th anniversary of that event, and the reason for the ride series.  We are partnered on this series with a non-profit group called Good City Group which is comprised of architects, designers, engineers and planners seeking to create methods of achieving healthier, sustainable cities.  This series augments the timing of their work on their Last Mile project, which focuses on transportation and commuting options after a commuter departs a train or bus station, and is centered in Jefferson Park, where my company Big Shoulders Realty has been for the past decade. Details for the remaining rides this year are here on the Chainlink and on

CL: How many bikes do you currently own?

LD: An absurd amount. Between my own bikes, and bikes I’ve built as the loaners for the tour it is at least a couple of dozen.

CL: What’s your favorite bike?

LD: My favorite to ride fast is my Ridley Fenix.  My favorite to ride chill is my 60th Anniversary Paramount.

Tour of Rogers Park 2012. Photo by Gabe.

Upcoming Tours Hosted by Lee Diamond

Tour of Rogers Park – July 23

Chicago Community Area #1, Rogers Park sits 9 miles north of the Loop. It was formerly land used by the Pottawatomi Nation and other indigenous people. Present day Ridge and Rogers Avenues were both former native trails and Rogers formed part of the Indian Boundary Line decreed in the 1816 Treaty of St. Louis. The streets of Rogers Park are likewise lined with amazing homes and apartments which may lack such heralded pedigree or historical significance, but make up for it in simple, utilitarian and enduring beauty. The area is rich in stories to hear, features to discover and is well-suited for exploration on two wheels.

Tour of Jefferson Park – August 20

Jefferson Park, Chicago Community Area #11 is 10 miles northwest of the Loop. Nicknamed, the “Gateway to Chicago”, farmers once came from far and wide to sell their goods in Jefferson, named to honor Thomas Jefferson. Jefferson’s ideal location began as two Native American trails, grew to include the area’s earliest toll plank roads, and was thereafter augmented by rail and commuter lines. Today the area has a population of over 40,000, a tremendous amount of green space, historical homes and buildings throughout, and a namesake park on the National Register of Historic Places. Hop on your bike to visit an extra and intra-urban experience that barely feels like Chicago at the same time that it typifies it.

Tour of Forest Glen – September 3

Forest Glen is community area #12 and sits 10 miles northwest of downtown Chicago. Bordering the Northern border suburbs of Niles, Skokie and Lincolnwood, Forest Glen was a suburb itself until it was annexed by the city in 1889. The surrounding forest preserves, golf courses, parks, cemeteries, bike and hiking trails and beautiful homes of varying vintage and styles still preserves a suburban-community look and feel on the edge of the city. Our tour takes on a circuitous route of the side streets, park district paths and main arteries of a northwest community that includes the neighborhoods of Edgebrook, Old Edgebrook, Sauganash, Wildwood and Forest Glen, the neighborhood within the same named Community Area. We’ll get a chance to take in significant, but hidden architectural gems including works by Meyer and Cook, Clarence Hatzfeld and C. W. Lampe and Co. In all, the course is just over 17 miles and features stretches of peaceful bike trails through city parks and forest preserves.

Prairie Tour Two – October 15

Chicago is well regarded for its diverse architecture, but is particularly fortunate to have many examples of Prairie School architecture.  The Prairie School of architecture is one of America’s indigenous art forms and the most iconic modern architectural style, and it originated in and around Chicago. Commonly identified for wide, low slung forms with overhung roofs, horizontal scale and elements and natural earth toned colors, the building style mimicked the environs from where it was born. Its greatest practitioners including Frank Lloyd Wright, Walter Burley Griffin, Dwight Perkins, George Maher and other giants of Prairie design left stunning examples of Prairie School architecture in institutional, commercial, religious and residential buildings throughout Chicago.  This is a brand new tour focusing on the Prairie School of Architecture found on Chicago’s northeast side including sections of the original Indian Boundary.

Tour of West Ridge – November 5

West Ridge is Community Area #2, 9 miles northwest of the city’s Loop. The tour begins at the National and Chicago Landmark Park, Indian Boundary Park at 2500 W Lunt Ave in front of the recently fire-damaged Clarence Hatzfield designed Tudor fieldhouse with Native American motifs. The park is part of the northern boundary of the area that the Potawatomi seceded to the U.S. in 1816. West Ridge sits on a natural ridge, remnants of the glacial path that shaped the Great Lakes region. Following centuries of use by indigenous people, West Ridge was settled in the 1830s by immigrants who came to the region to farm the land. It is a popular and comfortable locale with jaw dropping mansions and a fleet of sturdy and tiny worker’s homes. Come join us on a leisurely bike ride to get to know the community, its history and architecture.


You need to be a member of The Chainlink to add comments!

Join The Chainlink


© 2008-2016   The Chainlink Community, L.L.C.   Powered by

Disclaimer  |  Report an Issue  |  Terms of Service