Kidical Mass Chicago
When: Third Sunday of every month
Where: Lincoln Square
Got a pintsize pedaler? This series of family-friendly rides returns from its winter hiatus with events in neighborhoods all over town, rain or shine. chicagokidicalmass.org
Chicago Critical Mass
When: Last Friday of every month
Where: Loop
Annoying evening commuters for more than a decade! Critical Mass is the huge bike ride on the last Friday of every month that you’ve always wanted to join but never got around to. This is your month. facebook.com/chicagocriticalmass
Chicago Velo Prairie Tour
When: May 14
Where: Old Irving Park
Sure, the architectural boat tours are great for showing tourists around, but why not go off the beaten path to explore some of Chicago’s hidden Prairie gems up close—and get a little exercise in the process. chicagovelo.com
Ride of Silence
When: May 18
Where: Loop
Ever passed a white “ghost bike” memorial at a busy intersection? This slow and silent ride honors those injured or killed while cycling. rideofsilencechicago.weebly.com
MB Bike the Drive
When: May 29
Where: Lake Shore Drive
Experience the sunrise from the spot of your choice on the usually gridlocked Lake Shore Drive, with start times as early as 5:30. Register soon: The much-loved event (now in its 15th year) is expected to attract more than 20,000 cyclists. bikethedrive.org
Bike Commuter Challenge
When: June 10 to 17
Join thousands of riders from more than 500 Chicago-area organizations as they compete to log the most bike mileage in a week. New for 2016: an app to track your mileage. Proceeds benefit the Active Transportation Alliance. bikecommuterchallenge.org
World Naked Bike Ride
When: June 11
Where: TBA
Yes, it’s exactly what it sounds like. “But why?” you ask. To promote “people-powered transport” and body positivity. (And because sometimes the wind in your hair just isn’t enough.) chicagonakedride.org
Grand Illinois Trail and Parks Bike Tour
When: June 12 to 17
Where: Coal City
Now in its 14th year, this six-day ride showcases the state’s Route 66 Trail and draws visitors from around the world. Pitch a tent in parks along the way or get on the lengthy waitlist (now!) for a motel. rideillinois.org/events/gitap
Green Music Fest
When: June 18 to 19
Where: Wicker Park
Summer festival season reaches critical mass with Green Music Fest, which takes over a stretch of Damen between North and Schiller. The south stage is powered entirely by a fleet of stationary bikes, operated by volunteer riders (read: you). greenmusicfestchicago.com
Tour de Fat
When: July 9
Where: Palmer Square
Part circus sideshow, part beer release event, part fundraiser. Join New Belgium Brewing’s joy-filled bike parade through Chicago for a suggested $5 donation, which benefits West Town Bikes’ youth cycling programs. newbelgium.com/events
Un Tour des Femmes
When: July 9
Where: Normal
Looking for a ride free from the oppressive headwind of the patriarchy? Ladies, this one’s for you. Choose the 25- or 50-mile course, with plenty of estrogen-fueled encouragement along the way. thechainlink.org/events/un-tour-des-femmes
Ride for AIDS Chicago
When: July 9 to 10
Where: Evanston
This two-day, 200-mile trek to Elkhorn, Wisconsin, and back is demanding, but that thigh burn will be a righteous one: The $1,000 minimum that riders must raise goes to the Test Positive Aware Network’s local programs. tpan.com
Wright Ride
When: August 21
Where: Oak Park
The course ambles through the town’s picturesque streets and beyond (a 68-mile option goes way beyond, to Western Springs). Along the way, you’ll take in 12 of Frank Lloyd Wright’s iconic Prairie-style landmarks. oakparkcycleclub.org/wright-ride