Midwest Cycling Clubs

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Cycling clubs are one of the best groups to be involved with for those who love to bike, race, or develop the abilities, knowledge and relationships with people with a similar love for cycling. However, clubs have varied purposes and makeups depending on what one is seeking.

I connected with a few clubs in the Chicagoland area to shine a light on some of the latest happenings, different clubs, as well as to show the diversity that exists in our city. Here are a few cycling clubs you definitely want to know about.

Misfits Cycling Club


Kevin Carter started the club after two years of running Major Taylor Chicago on January 1, 2019 with the mission for Misfits Cycling to ride for fun, health and to push each other to be better. This is a carefully selected group of cyclists with some of the same cycling mindsets.

In 2019, Kevin shares that “we had some fun traveling trips. We went to Dayton, Canada, Atlanta, Detroit, and a few other places. We had some really nice weekend rides at home. Our Tuesday Taco ride became a big hit all year.”

“I think our members like most about our club is we do us! We don’t have a bunch of stuck up rules. Everyone in the club is experienced and we respect each other’s ride. The entire club is about cycling and fun”, Kevin emphasizes.

Misfitscycling@gmail.com is where you can connect with them, however, it is a closed group and if you get in it’s because you add value to the club and the club adds value to your cycling life.

Keep an eye out for them all over the city. They have a team clothing line so you might see them in different uniforms. This is a fun club that keeps it fresh and stylish.

Spidermonkey Cycling


Spidermonkey Cycling is an all-inclusive cycling club based out of Chicago. They have members that are serious about racing as well as those uninterested in racing, and many in between. They encourage riders of all interests and abilities to get on a bike and ride. Their mission is based on completion rather than competition, but our main focus is just to have fun!

They have a number of public rides. On Saturday mornings there is a beginner’s group ride. On Sundays there is a quicker, not for beginners group ride, and Tuesday mornings they have a ladies only ride.

In addition to weekly group rides they are involved in a few events. The two main events are the Montrose Cyclocross race and the Ricky Bobby Charity ride. Montrose CX is a cyclocross race that is part of the Chicago Cross Cup series. It’s the last race of the season and takes place at Montrose Beach towards the beginning of December. Spidermonkey puts on that race and usually draws upwards of 700 racers. The Ricky Bobby ride is a charity ride they put on, taking place in Fennville,Mi at Virtue Cider. The ride is 100 miles and benefits Urban Initiatives here in Chicago.

Last year The Ricky Bobby charity ride raised almost $13,000. Spidermonkey Cycling has raised over $150,000 for charity since the team started in 2007. And they just won the USA Cycling Club of the Year for 2019!!!

“I think what people like about the team is we are the like the Swiss Army knife of teams, there’s something for everyone. We’ve had elite racers who race road, track, cyclocross, and mountain . We have Ironmen, triathletes, ultra-runners and swimmers. We also have people that just enjoy riding for fun and fitness!” states David Donnelly.

The best way to get in contact is through our website www.spidermonkeycycling.com or contact@spidermonkeycycling.com

Training Wheels Optional (T.W.O.) Cycling


In August of 2018, as a result of hypertension (high-blood pressure) and the need to get it under control, the cycling that Alan Homan once just did for fun developed into him doing longer rides. On a vacation, a cycling jersey he designed became popular within a small group of friends and led to the formation of Training Wheels Optional (T.W.O.) Cycling Club.

With Caliph Jackson and Kathy Gray soon on-board to help with the structure and organization, over 40 members joined in the first 4 months along with a social media following of over 100 local and out of state riders and cycling clubs.

T.W.O.’s mission is to get as many people on bikes as we can and to show those people through training and mentoring that almost ANYONE can ride their bike for a hundred miles. It’s not a speed thing. It’s not even an expensive bike thing. It’s just a matter of keeping the pedals moving.

Between May and September 2019 they completed over 13 rides of 40 miles, 7 rides of 60 miles or more and completed 4 century rides. They helped 18 riders complete their first century rides, which included one rider successfully completing her first real IRONMAN Triathlon race in Arizona.

For 2020, by late March or early April, there will be some training for their first wave of riders that want to complete their first Century Ride. By early June they should be in full swing and should have a ride calendar schedule published for the 2020 summer and fall seasons.

Part of their calendar will include rides from other local clubs as well as clubs out of state, as well as continuing to holding rides in Chicago, Naperville, Lansing, Alsip, Chesterton, Hobart and, in Union Pier, Michigan. Additionally, for 2020 they are scouting routes and rides for the Elgin, Aurora, Marseilles and Joliet areas.

Alan expresses that “People who ride with us say that they like all of the encouragement we give on our rides. If a weaker rider falls back there is always someone to drop back and ride with them for moral support. We try to make people feel welcome. The people we ride with become our friends and these friends bridge the spectrum of what Chicago has to offer.”

People can contact T.W.O. via email at: twocyclingchicago@gmail.com. They hold club meetings at Goodspeed Cycle in Homewood, IL.

Black Girls Do Bike


Black Girls Do Bike (BGDB) Chicago Chapter is one of 85 chapters throughout the USA and Antigua, with more than 15,000 members and a local chapter of approximately 750 members. They are a cycling organization with an interest in growing and supporting a community of women who share a passion for cycling. They seek to engage/introduce ALL women to the joys of cycling but especially women of color.

The Chicago BGDB chapter offered 9 standing rides to our members, during the 2019 cycling season (five of which occurred weekly). The rides ranged from developmental rides to intermediate to advanced and took place in Chicago, the western suburbs, the southern suburbs and Indiana. They participated in rides that supported a variety of initiatives including Ride of Silence (in memory of people who have been killed/injured while riding a bike), the Ovation Cancer Research Alliance indoor spin fundraiser and a Breast Cancer Awareness ride. They also supported local cycling clubs by participating in Joliet 4th of July Ride, North Shore Century, Folks on Spokes Easter Ride, Wright Ride, as well as, several out of state rides.

For 2020, the Chicago BGDB chapter is hosting the annual National Meetup, during the 2020 Memorial Day weekend and have invited members from all over the country to participate in the city’s signature Bike the Drive. During the May 22-25 weekend, they will host several activities including a ‘Welcome to Chicago Dinner’, a Bike Tour of Chicago, the Meetup Party (with dinner, a DJ and plenty of giveaways from our sponsors) and a Memorial Day bike ride.

BGDB co-lead, Celeste Adams expresses, “We provide a comfortable place where female cyclists can advise, support, promote learning opportunities and participate in group rides at all levels. We are a friendly group of women who value any time that we get to hop on a bike and ride.”

You can find more information and contact BGDB on the national website https://www.blackgirlsdobike.com/ or on the BBGD Chicago Facebook page, https://www.facebook.com/groups/BlackGirlsDoBikeChicago/ or through email at BGDBChicago@gmail.com.

Other cycling clubs in the Chicagoland area include:
Major Taylor Cycling Club: http://www.majortaylorchicago.com/
Half Acre Cycling: http://halfacrecycling.org/

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