Organized Bike Rides in Illinois


2022 update some dates TBD

One of my favorite past times is riding my bike on the lakefront in Chicago and participating in organized bike rides in Illinois. 

Right now, I haven't been biking in the house to get ready for the cycling season. I'm really out of cycling shape. Every Sunday and one time during the week, I would train on my stationary bike to prepare my lungs and legs for spring, summer, and fall. I will start today but with that said, below are some of my favorite organized rides around the state.

September 4, 2022   May Bike the Drive (Chicago)
*This bike ride has moved to the fall season.
This is my first bike ride of the season and it is a big one. Every year the city of Chicago closes down the iconic Lake Shore Drive to cars to allow a morning of biking the drive. It starts at 5 am and you can start anywhere on the lakefront or at the starting line which is in Grant Park, downtown Chicago. It is open to anyone from children to advanced cyclists. The total miles are 30 but some people will do it twice to get in longer mileage. You can also do less than 30 miles, you can stop anytime you like. Register online 

July 10, 2022   Swedish Days Ride (Maple Park IL)
This year will be the Fox Valley Bicycle and Ski Club's 50-year anniversary. Most of the tour is on quiet, scenic, paved country roads. Bring extra cash because they will be selling their 50th-anniversary moisture wicking t-shirts and cycling jerseys. Routes include 25-Miles, 50-Miles, 62-Miles (Metric Century), 100-Miles (Century), and 124-Miles (Double Metric). All distances are approximate and subject to change until early June. Register online

July 4, 2022    Fourth of July Century (Plainfield IL)
The fourth of July Century is my favorite thing I do on holiday. It is also in the country and you are cycling on quiet small town roads. This year's course has been finalized and it is 30, 50, 75, and 100-mile routes. One of the best ways to start on the 4th of July is before you check out any picnics or barbeques. Register online 

July 17, 2022     Biking with Beanzie ((DeKalb IL)
This bike ride also consists primarily of flat rural roads but with some rolling terrain. I think I have done it one time a while ago but as I remembered it was enjoyable. Routes go through scenic DeKalb, Ogle, and Lee County windmill farms and the Beanzie offers 3, 5, and 8-mile family-friendly, community bicycle pathway routes as well.  The longer routes are 25, 64, 80, and 101 miles  Register online 

August 7, 2022    Two Rivers Century (Kankakee IL)
I haven't done this one but I heard a lot about it. If you would like to see a two Frank Lloyd Wright homes, two rivers the Kankakee and Iroquois, barn quilts and more then this is the one you must do. Miles: 22-128  Register online

August 18, 2022    Bike Psychos Century (Coal City)
Like many of the above bike rides, the Bike Psychos Century is a majestic journey through the fertile fields and back roads of America's small country towns. I have always wanted to do this one too but something always came up that week. Routes: 35, 50 75 100, 124-mile route to choose from.   Register online 

September 17, 2022   Amish Country Bicycle Tour
Choose routes approx. 20, 42, or 60 miles through small rural villages of Arthur, Atwood, and Arcola. You will be on route choices that are well marked. Register online

September 18, 2022   North Shore Century (Evanston IL)
This one I have done twice. It is through some of the most scenic and ritziest neighborhoods north of the city of Chicago. However, when I did it years ago there was no fundraising commitment to the tour. If you don't mind raising money for The Leukemia & Lymphoma Society, a noble cause, then you should do this one especially to see some of the magnificent homes that are in the North Shore.  $1,600 - Entry Fundraising  Routes: 25, 50 62, 100 miles Register online 

(TBD) October?  Pumpkin Pie Bicycle Ride (Ottawa IL)
The last time I did this one, they promised hot chocolate, chili, and some comfort food to keep you warm for this autumn ride. However that day, it was hot as hades and I stopped after 15 miles. It was in the nineties and I don't think it has been that hot for that ride since. Anyway, I think this will be my last ride of the season. Ride to see the start of the changing of the leaves. Routes: 27, 42, 63, or 103 miles   Register online 


  1. I love the one that they have every year where you can bike on Lake Shore Drive!


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