Kidical Mass Chicago
Kidical Mass Chicago Photo: Oren Miller

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.

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.

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.

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.

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.

Bike Commuter Challenge
Bike Commuter Challenge Photo: Active Transportation Alliance

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.

World Naked Bike Ride
World Naked Bike Ride Photo: Mikey Brick

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.)

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.

Green Music Fest
Green Music Fest Photo: Courtesy of Green Music Fest

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).

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.

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.

Ride for AIDS Chicago
Ride for AIDS Chicago Photo: Kelly Allison

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.

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.