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Group Rides & Bike Routes in Chicago

Looking for group rides in Chicago? Checking for USA CYCLING clubs and BIKE SHOPS are a great starting point in any big city. Here are a few well known rides and routes we recommend starting with:

xXx Racing-Athletico Saturday Team Ride info: xxxracing.org/ride
xXx-Racing Athletico is nationally recognized as having won USA CYCLING’s “Club of the Year” award multiple times for good reason – while their cycling kits might look fast & intimidating, they are one of Chicago’s largest cycling teams for all ages & ability levels from youth to masters. From social “donut rides” to “practice crits” to teach people about racing, you can find a little bit of everything in their club. Their Saturday “team ride” is open to all as one of Chicago’s largest group rides, and a great place to start to meet and learn about cycling communities in Chicago. Typical Saturday Route: https://www.strava.com/routes/17547819

BFF Bikes Shopbffbikes.com/events – They typically rotate alternating weekends of “beginner” friendly rides and longer/faster “endurance” rides. Here is their typical “Endurance” Ride Route: tinyurl.com/bffride

The Chainlink – a generally good resource for all things cycling related in chicago. Check their resources page for links to bike shops, routes, etc.: thechainlink.org/page/useful-links

Additional Rides, Routes, and Events – For additional routes, maps, and century ride events, visit our old “TriMonster Rides” google doc below (but note that some of the information here might be out dated). Some great “hidden gem” ride routes to “explore” if you’re looking for a first “cycling adventure” to ride heading out of the city, includes the “North Branch Trail“: https://fpdcc.com/places/trails/north-branch-trail-system/

Chicago Virtual Cyclists (CVC) – follow, meet, and connect with other cyclists around Chicago virtually through our open and free “CVC” community! This is a great place to ask for recommendations, and even meet others to ride with outdoors (after surviving the Chicago winters on your trainer!). Learn more at 4starendurance.com/cvc

Lakeshore Landsharks – join our beginner-friendly triathlon community that feature “brick” workouts and “triathlon clinics” on the weekends, typically starting around Foster Ave on the lakefront on Saturday mornings. Learn bike handling skills, transition skills, and even how to fix a flat tire! Learn more and join at 4starendurance.com/landshark

If you know or would like to share ride and route information here – simply contact us and we’re happy to add more to this page!

FYI: If you’re a triathlete, please be aware that most “group rides” in Chicago imply riding close to other athletes on city streets and bike lanes that require you to react quickly to braking and shifting gears. Most “time trial” or “triathlon” specific bikes are not as safe in group ride settings (or on the lakefront trail) where quick reaction time is important for safety for both yourself and others around you, because these types of bikes typically do not have shifters+brakes “integrated” like road bikes do – they typically have the brakes (on handlebars) and shifters (on aero bar ends) separated, thus preventing you from quickly reacting to both shifting and braking without having to move your hand position. Most group rides will not welcome “TT” bikes like this for these safety reasons, even if you may have electronic shifting and the ability to shift easily from the brake hoods, because “time trial” bikes are not as agile on city streets. Please check with group ride leaders in advance for “time trial” and “triathlete friendly” group rides – as some may ask and require you to ride “at the back” or ride “off the front”. Check for USA Triathlon certified clubs and coaches for recommendations on triathlete-friendly group rides and routes.

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