Rides and Events

Check this page often for updated listings of all types of cycling events in and around our area. Rides require, at minimum, an appropriate bike in good working order, water, and a helmet. We suggest a spare tube, energy food, maybe a little cash in case we stop, and your biggest smile! Many rides are held subject to weather. It's a good idea to confirm dates, time and any specific requirements, too. We'll see you out there — and have fun!

Upcoming Cycling Events

Some of these events require fund-raising to benefit charitable organizations. Call for further information.

Date Event Name Location Description Phone

May 27, 2018

Bike the Drive

Chicago, IL

Catch the view on Lake Shore Drive! Don’t let the cold stop you from planning your summer fun. Enjoy great views of the lake, the city’s stellar skyline and many thousands of other cyclists celebrating two-wheeled freedom.

Jun 3, 2018

The Udder Century

Crystal Lake, IL

Come join us for an udderly good time at the annual Udder Century. Pedal (and steer…) along flat to rolling rural routes of 31, 50, 63, 76, or 100 miles through the dairy land of northern Illinois and southern Wisconsin . Be sure to take breaks along the way at our strategically placed rest stops to refuel, refresh, and chow down on bagels, fruit, cookies and energy drinks. After the ride, swap bike tales with fellow cyclists while enjoying a Heifer-ty Pasta Dinner

Jun 8, 2018

American Lung Association Fight for Air Ride

Crystal Lake, IL to Lake Geneva, WI

Join cyclists of all levels for the Annual Lake Tour Bike Trek. Challenge yourself to ride 50 miles each day for personal achievement, a new cycling experience, or to honor a loved one affected by lung disease. Choose a 2 day ride or a 3 day ride. Participants are treated to a weekend stay including accommodations and catered meals at the fabulous Abbey Resort on Geneva Lake. This is a ride that you can't miss.

(312) 781-1100

Jun 10, 2018

Ramble Recreational Bike Ride

Wilmot, WI

Routes of 25, 46, 62,82, and 100 miles. Your Ramble fee includes marked roads, maps, SAG, rest stop with food and live music, plus post-ride cookout and more

Jun 10, 2018

American Diabetes Association Tour de Cure

Aurora, IL

Chicagoland Tour de Cure is more than just a cycling event. It's a life-changing event. A day full of fun and excitement where riders of all levels join forces in the fight to Stop Diabetes® and raise critical funds for diabetes research, education and advocacy in support of the American Diabetes Association.

Jun 10, 2018

Grand Illinois Bike Tour

Clinton, IL

June 10- 15, 2018 - Daily basic routes range from 44 - 52 miles with longer route options available.

Jun 16, 2018

Janesville Pie Ride

Janesville, WI

Choice of 12.5, 32, 62, or 100 mile routes. All registered riders will receive a delicious pie at the finish line.


Jun 23, 2018

Bike MS: Tour de Farms

Geneva, IL

The Tour de Farms is a 1 or 2 day ride with multiples routes from 35-175 miles. The money that is raised will help create a world free of MS.

Jun 24, 2018

Swedish Days Ride

Hampshire, IL

Options include 29 to 128 mile choices touring quiet, scenic, paved country roads

Jun 24, 2018

2 Wheels for 2 Counties

Kansasville, WI

Choose between 25, 44, 62, or 100 mile routes for your level of enjoyment or challenge.


Jul 15, 2018

Biking with Beanzie

DeKalb, IL

Biking with Beanzie is a recreational ride presented by Kishwaukee Kiwanis Club of DeKalb and sponsored by Kishwaukee Community Hospital. The ride route consists of primarily flat rural roads with some rolling terrain with estimated ride options of 25 to 101 miles. All roads are well-paved, lightly traveled and posted with signs containing ride information and bits of Beanzie humor. Also available are 3-mile 5-mile, & 8-mile family friendly community bicycle pathway route options.

Jul 21, 2018

Venus de Miles

Lake Forest, IL

Venus de Miles is a lot of things – Northern Illinois’ first all-women’s road ride, a celebration of sisterhood, support for Greenhouse Scholars, and crazy fun – but one thing it’s not is a race. So, don’t be afraid to walk your bike up that hill, and, most importantly, enjoy yourself.

Jul 21, 2018

Ride the Shore For a Cure

Mequon, WI

A 2 day ride along the scenic shore of Lake Michigan to support the Leukemia & Lymphoma Society


Aug 5, 2018

Two Rivers Century

Kankakee, IL

Kankakee County boasts both the Kankakee and Iroquois rivers, each a treat to see. Along the route you will see not only the two rivers but many other scenic and historic places. Using our "Loop System" of routing you can ride as short as 22 miles or go as far as 128.

(815) 939-1311

Aug 12, 2018

Napaerville Rotary Ride

Naperville, IL

The ride offers a 1.4 mile family loop, 21, 41, and 62 mile routes.

Aug 18, 2018

Ride Like An Egyptian

DeKalb, IL

Join us for a fun and enjoyable bike ride through DeKalb and Kane counties while supporting the historic Egyptian Theatre. Since the ride starts and ends at the Egyptian Theatre you will have an opportunity to explore this historic landmark.

Aug 18, 2018

CF Cycle For Life

Maple Park, IL

The Cystic Fibrosis Foundation will host its annual Chicago Cycle for Life Ride.Choose from a 10, 30, or a 65 mile route. After the ride stay for the finish line party.

(312) 619-3925

Aug 19, 2018

Wright Ride

Oak Park, IL

The Wright Ride is named for one of Oak Park's most famous citizens, Frank Lloyd Wright. Distances range from 10 to 72 miles.

Aug 19, 2018

Bike Psychos Century

Coal City, IL

The Bike Psychos Century is a majestic journey through the fertile fields and back roads of America's heartland, punctuated by dramatic descents and challenging climbs of the Illinois River Valley

Sep 7, 2018

Capital City Century Weekend

Springfield, IL

One of the oldest cycling events in Illinois and is expanded in to a whole weekend of rides and fun

Sep 9, 2018

Harmon 100

Wilmot, WI

A non-competitive, scenic ride of 25, 50, 75 and 100 miles. Well marked and quiet country roads, cue sheets, SAG support, friendly volunteers and our well-stocked rest stops that receive RAVE reviews every year.

Sep 9, 2018

Easter Seals Bike for the Kids

Elgin, IL

Choose from a 12, 25, 50, or 100 mile route or a 2.5 mile family fun ride for all ages and abilities

Sep 15, 2018

Lorie's Lakeside Century

Chesterton, IN

Experience the beauty of our casual coastal and country. Since we started in 1980 our ride has been known for great routes, friendly volunteers, and tasty food.

(219) 462-4185 x350

Sep 16, 2018

The North Shore Century

Evanston, IL

The North Shore Century offers incredibly scenic biking. You'll experience luxurious neighborhoods, view unique architectural treasures, pedal down tranquil tree-lined streets and feel the refreshing breezes of Lake Michigan. Open it up in the flat to rolling countryside between Chicago and Wisconsin.

Sep 30, 2018

Apple Cider Century

Three Oaks, MI (appox. 60 miles from Chicago)

Apple Cider Century celebrates its 45th annual ride with routes from 15 - 100 miles throught the orchards, forests, and wine country of southeast Michigan.Enjoy fresh Michigan apples and apple cider along the route.

(888) 877-2068

Oct 7, 2018

Pumpkin Pie Ride

Ottawa, IL

Rides from 27 to 103 miles are available. All riders enjoy pumpkin pie after the ride