A large group of cyclists in summer at the starting line of a bike ride in the country.

Bike in groups! Calendar of organized and charity rides, big events

by Neil Holdway | Posted on

This is a calendar and list of the prominent organized rides run by community and charity organizations in the Chicago suburbs or nearby. By no means is it all-inclusive. I’ll be regularly updating it. I’d be happy to add yours if I don’t have it.

Corrections made May 18: Pedalpalooza in McHenry County was really May 30; Feb. 22: Everybody Rides was really May 31, not June 21.

Ride Illinois’ redesigned events calendar: For more rides and events throughout the suburbs and Illinois, check out Ride Illinois’ redesigned calendar.

Also see Northern Illinois Cycling’s index of rides and races near us in the Midwest.

Click on links below (usually the date) to get each organized ride’s details, such as registration and costs.

Ongoing open rides, spring to October

Wheeling Wheelmen “Bakery Rides”

  • First Tuesday of every month from April to October.
  • Routes of 20, 30 or 40 miles. Downloadable.
  • Start at Willow Stream Park in Buffalo Grove
  • Not a supported ride
  • “Pick your route. Pick your pace.”

Crank Revolution rides starting in Hoffman Estates

  • 5 p.m. Wednesdays starting from this Hoffman Estates bike shop off Paul Douglas Trail
  • Rides of usually around 30 miles into South Barrington and Barrington Hills
  • Varying speeds: A (20 mph variety) and B groups
  • Not supported

Monthly community rides

Pedal & Spoke Ltd. rides starting in North Aurora

  • Monday Night Saw Wee Kee Group Rides: Organized mountain bike group ride starts at Saw Wee Kee Park in Oswego every Monday (weather and trail permitting). Riders start gathering in the second lot at the park around 5:30 p.m. and roll out at 6 p.m. The ride typically splits into two groups based on rider comfort and speed, and goes for about an hour and a half or however long the sun allows.
  • Tuesday Night Pedal & Social Rides: Rides will typically consist of a 20-25 mile mixed-terrain route connecting some of the surrounding trail systems. Pace typically averages a 10-12 mph social pace. Riders meet in front of the shop every Tuesday night (weather permitting) at 6 p.m. and roll out around 6:30. Call Graeme if you have any questions.

November

Bull Valley Run 200K ACP Brevet

  • Sunday, Nov. 1
  • By the Chicago Randonneurs club. Membership and check-ins required.
  • 124 miles (with time limit)
  • Starts at Double Clutch Brewing Company in Evanston
  • Route is west to Bull Valley, comes back through suburbs like Barrington and Wauconda

2027

Janesville Morning Rotary Club Pie Ride

  • Saturday, June 19. Tentative info:
  • Routes of 20K (12 miles), 50K (31 miles) or 100K (62 miles), plus a Family Fun Ride. Downloadable on Ride with GPS, Garmin and PDF.
  • Starts at Janesville, Wisconsin, Town Square, 65 S. River St.
  • Routes open 7 a.m. to 2 p.m.

Past 2026 rides

March

International Women’s Day Together We Ride

Wheeling Wheelmen St. Patrick’s Day Ride

  • Sunday, March 15
  • By the Wheeling Wheelmen club
  • 17- and 21-mile loops
  • Starts at Wauconda High School

April

Envision 2050 Open House, Lake County

  • Tuesday, April 14, 4-6 p.m.
  • Lake County is holding this public meeting about its project to outline its long-range for investing in transportation projects through 2050, including roads, paths and transit.
  • 2007 N. Civic Center Way, Round Lake Beach

MS Tour de Farms 2026 Spring Kickoff

Illinois Prairie Path Cleanup Day

Major Taylor Trail Cleanup Day

  • Saturday, April 25, 9 a.m. to noon
  • The Major Taylor Trail Keepers are leading a workday to trim trees and weeds and pick up trash.
  • Starts at 1630 W. 95th Street, Chicago
  • Registration required.

May

National Bike Month events: See separate article

Seeds & Stone Roubaix

  • Saturday, May 2, in Waterman
  • Benefiting the Hinckley Area Food Pantry and the Waterman Lions
  • Routes of about 25, 50 and 75 miles, all about three-fourths gravel
  • Kind of a race, but not if you don’t want to

MS Tour de Farms 2026 Spring Kickoff

  • Sunday, May 17
  • Part of Bike MS Tour de Farms fundraiser June 27-28 (below), but this is open to the public with registration for that ride available
  • 12 to 25 miles on Centennial Trail (paved) and I&M Canal Trail (gravel)
  • Details and RSVP via Facebook event
  • Starts at Imperial Oak Brewing, 501 Willow Blvd. Suite 100, Willow Springs. Pizza afterward.

Ride of Silence

  • Wednesday, May 20, 7 p.m. or maybe a little earlier
  • International event in memory of bicyclists killed on public roadways. Many suburban events.
  • Arlington Heights
    Contact: Mike Paulson   <–    Send email
    Distance: 10 and 15 miles
    Location: North School Park, N Evergreen Ave & E Eastman St
    RWGPS: Ride of Silence
  • Bartlett
    Contact: Terry Witt   <–Send email
    Distance: 8 miles easy pace of 12 mph on off-road and quiet streets.
    Starting and ending at the Bartlett Library, 800 S. Bartlett Road. Meet at the library 6:45 pm. Parent required for riders under 18.
  • Downers Grove
    Contact: Nanci Gasiel   <–Send email
    Distance: 4.5 mi.
    Place: Downers Grove Civic Center parking lot, 850 Curtiss Street Route: https://ridewithgps.com/routes/50255285
    Notes: Sign in at https://www.dgbikeclub.org/ride-sign-in
  • Elk Grove Village
    Contact: Dave Simmons   <–Send email
    Distance: 10 miles
    Starts and ends at the Al Hattendorf Center, 225 E. Elk Grove Blvd in Elk Grove Village.
    6:10pm – 6:30pm: Waivers and bike checks
    6:30pm – 6:40pm: RoS proclamation and safety discussion
    6:40pm – 8:00pm: Ride of Silence
    8:00pm – 8:30pm: Clean up
  • Elmhurst
    Contact: Kelli Morgan   <–Send email
    Distance: 10 miles
    Location: In front of Elmhurst police station on 1st Street, 125 E 1st St.
  • Evanston/Skokie
    Contact: David Barish   <–Send email
    Distance: 11 miles
    Location: Wheel & Sprocket, 1027 Davis St.
  • Naperville
    Contact: Justin White   <–Send email
    Distance: 10 miles
    Notes: Signup and waivers are at the Naperville Bicycle Club Strava event page.
    Location: 124 W Gartner Rd, Naperville

McHenry County Century Ride

  • Sunday, May 24
  • Routes of 25, 50, 62 and 100 miles
  • Starts at Sunset Park, 5200 Miller Road, Lake in the Hills

Pedalpalooza (McHenry County)

  • Saturday, May 30
  • By the Family Health Partnership Clinic in Crystal Lake
  • Scavenger hunt ride throughout McHenry County at your pace, using McHenry County Conservation District trails
  • Start and finish wherever and whenever you like, with stops at participating establishments
  • Optional fundraising promoting community heart health; registration required

Arlington 500

Everybody Rides

  • Sunday, May 31
  • Fundraiser for Project Mobility
  • Starts at James O. Breen Park, Campton Hills Road & Peck Road, St. Charles
  • Routes range from 1.6 to 62 miles

June

BCLC Ramble

Swedish Days Ride

  • Sunday, June 14
  • By the Fox Valley Bicycle & Ski Club
  • Routes range from 12 to 133 miles
  • Starts at Harter Middle School in Sugar Grove

Janesville Morning Rotary Club Pie Ride

  • Saturday, June 20
  • Routes of 20K (12 miles), 50K (31 miles) or 100K (62 miles), plus a Family Fun Ride. Downloadable on Ride with GPS, Garmin and PDF.
  • Starts at Janesville, Wisconsin, Town Square, 65 S. River St.
  • Routes open 7 a.m. to 2 p.m.

Pat Mac Ride

  • Friday, June 26
  • 100K (62 miles) from St. Barnabas in Chicago to Notre Dame Parish in Michigan City, IN.
  • Fundraising required to fight pediatric brain cancer.
  • The Pat Mac Ride honors the winning spirit and life of Patrick McNamara, who died at the age of 13 from a pediatric brain tumor. He was the child of Tom and Dee McNamara, the organizers of Pat Mac’s Pack.

Bike MS: Tour de Farms

Bike to the Barn – Ride from Anywhere (Naperville Area)

  • Saturday, June 27, 11 a.m.-2 p.m.
  • No single start location: Ride to the Greene Barn, 23W171 Hobson Rd., Naperville
  • Flexible event where you ride, walk, or run from wherever you are to the Greene Barn

July

Joliet Bicycle Club July 4th Ride

  • Saturday, July 4
  • Routes of 20, 30, 50, or 70 miles; downloadable
  • Starts at Kendall County Fairgrounds
  • “All routes on country roads only, no urban roads.”

August

Cowalunga Charity Bike Tour

  • Saturday-Monday, Aug. 1-3
  • By the Respiratory Health Association
  • Significant fundraising required
  • Routes from 18 to 190 miles over one or three days
  • Starts at Gurnee Mills Mall in Gurnee

Fox and Prairie Ride

  • Saturday, Aug. 1
  • By Partners In Mission Africa
  • Fundraiser ($195-$220 entry) for Kamwenge Secondary & Vocational School in Uganda
  • Routes of 28 and 50 miles on Illinois Prairie Path and Fox River Trail
  • Starts at First Presbyterian Church parking lot, 550 N. Main St., Glen Ellyn. Ends at Maplewood Brewery and Distillery, 486 Pennsylvania Ave, Glen Ellyn.

Two Rivers Century

  • Sunday, Aug. 2
  • Hosted by the Kankakee River Bike Club
  • Starts at the Splash Valley Aquatic Center, 1850 River Road, Kankakee
  • Six routes or loops offered of 8 to 26 miles each; can ride up to 101 miles
  • Ride with GPS files available

Raue Center for the Arts Night Owl Bike Ride

  • Saturday, Aug. 8, 9 p.m.
  • Register in advance or starting at 7:30 p.m. Saturday
  • Routes of 10 and 20 miles
  • Starts under the Raue Center Marquee, 26 N. Williams St., Crystal Lake
  • Ends at Raue Center, with an after-party

Naperville Rotary Ride

  • Sunday, Aug. 9
  • Put on by Naperville Sunrise Rotary each year, the second Sunday of August, to support local charities
  • Routes of 21, 43 and 62 miles
  • Starts at 3460 Lacrosse Lane, Naperville

Tour de Cure

  • Sunday, Aug. 9
  • By the American Diabetes Association
  • Significant fundraising required
  • Starts in Pottawatomie Park in St. Charles
  • Metric century, half-metric and “family fun” routes

Roun’da Manure Bicycle Tour

  • Saturday, Aug. 15
  • By the chamber of commerce of Sharon, Wisconsin, just over the border northwest of Harvard
  • Four loops of between 20 and 37 miles offered, available on Ride with GPS
  • Rest stops are at ice cream shops! BBQ lunch afterward at local bar.
  • See the review of the 2025 ride.

Double Eagles 400K ACP Brevet

  • Saturday, Aug. 15
  • By the Chicago Randonneurs club. Membership and check-ins required.
  • 248 miles (with time limit) into north suburbs, Wisconsin, far northwest and west suburbs
  • Passes through bald eagle sighting hotspots in Burlington and Antioch
  • Starts at Illinois Centennial Monument, Logan Square, Chicago

Des Plaines River Trail 160k Gravel Ride

  • Saturday, Aug. 22
  • By the Chicago Randonneurs club. Membership and check-ins required.
  • 100 miles (with time limit)
  • Starts at Robinson Woods-South in Chicago, goes to nearly Wisconsin border and back

Illini 200K, 300K, 400K RUSA Brevets, or 600K ACP Brevet

  • Starts Friday night, Aug. 28
  • By the Chicago Randonneurs club. Membership and check-ins required.
  • Four nighttime-to-daytime routes offered (with time limits), heading toward Champaign and back
  • Starts at the Target store in Oswego

Busse Woods Night Ride

Harmon Hundred

  • Sunday, Aug. 30
  • By the Wheeling Wheelmen Bicycle Club
  • “Non-competitive scenic ride through Lake County”
  • Routes of 25, 50, 75 and 100 miles. Downloadable and on Ride with GPS.
  • Starts at Wauconda High School

Hope Echoes on the River Charity Bike Ride

  • Sunday, Aug. 30
  • Fundraiser for CASA Kane County
  • Routes of 10, 35 or 65 miles
  • Starts at the Kane County Courthouse in Geneva

September

Let’s Ride, Illinois

  • 2026 “Let’s Ride, Illinois,” led by Ride Illinois over the entire month of September, is a series of events to celebrate the joy, freedom and sense of community that riding a bicycle brings to people of all ages and abilities.
  • Features “slow roll” bike rides of 10 miles or less, organized by community members, that are free and open to all.
  • Check the Ride Illinois web page for a calendar of specific events, locations and guidance.

The Midwest Tandem Rally

  • Friday, Sept. 4, to Monday, Sept. 7 (Labor Day weekend)
  • In Kalamazoo, Michigan
  • Ice cream ride Friday afternoon, sag-supported rides Saturday and Sunday, doughnut ride Monday morning
  • Saturday and Sunday rides start at 25 miles, with additional loops for those who want more

Bike the Drive

  • Sunday, Sept. 6
  • On a closed-to-autos Lake Shore Drive in Chicago
  • By the Active Transportation Alliance
  • Can ride the drive from 6:30 to 10:30 a.m.
  • Ride all or part of 30-mile loop, or ride it multiple times
  • Read a review of the 2025 ride.
  • See how it looks on this video, or what the wind sometimes is like in this video.

North Shore Century

  • Sunday, Sept. 20
  • By the Evanston Bicycle Club
  • Routes from 25 to 100 miles
  • Starts at Lakeview Center at 800 Gillson Park Drive in Wilmette and runs north

Tour of Scenic Ogle County Bike Ride

  • Saturday, Sept. 26
  • By the Village of Progress charity for people with disabilities
  • Routes of 10, 32 and 62 miles
  • Starts at the Village of Progress, 710 S. 13th St., Oregon

Apple Cider Century

  • Sunday, Sept. 27
  • Popular ride (like 4,000 riders) out of Three Oaks, Michigan
  • Routes of 15, 25, 37, 50, 62, 75, or 100 miles

Past 2025 rides

March

International Women’s Day Together We Ride: Anybody can ride anywhere, any distance March 8-11 (especially Saturday, March 8) to celebrate the achievements, persistence and future of women and girls all around the world. Started in 2020 by Dawn Piech. Here’s a list of rides in the suburbs on March 8 (thanks to Ralph Banasiak).

Wheeling Wheelmen St. Patrick’s Day ride

May

Rock River Madness

  • Saturday, May 3, in Dixon
  • By the Rock River Valley Bicycle Club
  • Routes of 6, 10, 13, 55 and 100 miles
  • Starts at Dixon Park District facility, 1312 Washington Ave.

Seeds & Stone Roubaix

  • Saturday, May 3, in Waterman
  • Benefiting the Hinckley Area Food Pantry and the Waterman Lions
  • Routes of 25, 55 and 75 miles, all about three-fourths gravel
  • Kind of a race, but not if you don’t want to

Pastry-Bike-Pastry 2025

  • Sunday, May 4
  • Self-supported, mixed-terrain ride featuring several checkpoints stocked with doughnuts from local bakeries
  • By Pedal & Spoke Ltd. Bicycles in North Aurora
  • 25, 65 or 100 miles. 32mm tires recommended

Pedalpalooza (McHenry County)

  • Saturday-Sunday, May 17-18
  • By the Family Health Partnership Clinic in Crystal Lake
  • Scavenger hunt ride throughout McHenry County at your pace, using McHenry County Conservation District trails
  • Start and finish wherever and whenever you like, with stops at participating establishments
  • Optional fundraising promoting community heart health; registration required

Tour de Farms 2025 Spring Kickoff

  • Sunday, May 18
  • Part of Bike MS Tour de Farms fundraiser June 21-22, but this is open to the public with registration for that ride available
  • 12 to 25 miles on Centennial Trail (paved) and I&M Canal Trail (gravel)
  • Details and RSVP via Facebook event
  • Starts at Imperial Oak Brewing, 501 Willow Blvd. Suite 100, Willow Springs. Pizza afterward.

Everybody Rides

  • Sunday, May 18
  • Fundraiser for Project Mobility
  • Starts at James O. Breen Park, Campton Hills Road & Peck Road, St. Charles
  • Routes range from 1.6 to 62 miles

Ride of Silence

McHenry County Century Ride

  • Sunday, May 25
  • Routes of 25, 50, 62 and 100 miles
  • Starts at Sunset Park, 5200 Miller Road, Lake in the Hills

June

Arlington 500

  • Sunday, June 1
  • By the Arlington Heights Bicycle Club
  • Routes range from 20 to 101 miles
  • Starts at Lake Zurich High School

Ride for the Troops

  • Sunday, June 1
  • By Trek Bicycle Store of Naperville and Downers Grove, and Webb Chevy Plainfield
  • Benefits the troops via USO, with entry fee and raffle
  • Routes of 10 or 20 miles
  • Starts at Webb Chevy Plainfield, 16140 S. Lincoln Hwy.

BCLC Ramble

  • Sunday, June 8
  • By the Bicycle Club of Lake County
  • Four different loops with distances totaling 25-100 miles
  • Starts at Wilmot Mountain Tubing Chalet, just over border in Wisconsin
  • Routes open 6 a.m. to 4 p.m.

Janesville Morning Rotary Club Pie Ride

  • Saturday, June 14
  • Routes of 20K (12 miles), 50K (31 miles) or 100K (62 miles), plus a Family Fun Ride. On Ride with GPS.
  • Starts at Janesville, Wisconsin, Town Square, 65 S. River St.
  • Routes open 7 a.m. to 2 p.m.

Pat Mac Ride

  • Friday, June 20
  • 100K (62 miles) from St. Barnabas in Chicago to Notre Dame Parish in Michigan City, IN.
  • Fundraising required to fight pediatric brain cancer.
  • The Pat Mac Ride honors the winning spirit and life of Patrick McNamara, who died at the age of 13 from a pediatric brain tumor. He was the child of Tom and Dee McNamara, the organizers of Pat Mac’s Pack.

Bike MS: Tour de Farms

  • Saturday-Sunday, June 21-22
  • By the National MS Society
  • Significant fundraising required
  • 25, 62 or 100 miles
  • Starts at Kuipers Family Farm, Maple Park

Swedish Days Ride

  • Sunday, June 29
  • By the Fox Valley Bicycle & Ski Club
  • Routes range from 12 to 133 miles
  • Starts at Harter Middle School in Sugar Grove

July

Joliet Bicycle Club July 4th Ride

  • Friday, July 4
  • Routes of 20, 30, 50, or 70 miles
  • Starts at Kendall County Fairgrounds (new this year)
  • “All routes on country roads only, no urban roads.”

August

Cowalunga Charity Bike Tour

  • Saturday-Sunday, Aug. 2-3
  • By the Respiratory Health Association
  • Significant fundraising required
  • Routes from 18 to 135 miles over one or two days
  • Starts in Gurnee

Fox and Hound Bike Ride

  • Saturday, Aug. 2
  • By PIM Africa
  • Fundraiser ($195 entry) for vocational program at a school in Uganda
  • Routes of 25 and 50 miles on Illinois Prairie Path and Fox River Trail
  • Starts at First Presbyterian Church parking lot, 550 N. Main St., Glen Ellyn. Ends at Two Hound Red, 486 Pennsylvania Ave., Glen Ellyn.

Raue Center for the Arts Night Owl Bike Ride

  • Saturday, Aug. 2, 9 p.m.
  • Register in advance or starting at 7:30 p.m. Saturday
  • Routes of 10 and 20 miles
  • Starts at Crystal Lake city hall, 100 W. Woodstock St.
  • Ends at Raue Center, with an after-party

Tour de Cure

  • Saturday, Aug. 9
  • By the American Diabetes Association
  • Significant fundraising required
  • Starts in Pottawatomie Park in St. Charles
  • Routes between 5 and 63 miles last year

Naperville Sunrise Rotary Ride

  • Sunday, Aug. 10
  • By the Naperville Sunrise Rotary Club
  • Starts in Commissioners Park in Naperville
  • Routes of 20, 40 or 60 miles

Roun’da Manure Bicycle Tour

  • Saturday, Aug. 16
  • By the chamber of commerce of Sharon, Wisconsin, just over the border northwest of Harvard
  • Four loops of between 17 and 36 miles offered
  • Rest stops are at ice cream shops! BBQ dinner afterward.

Busse Woods Night Ride

Bike the Drive

  • Sunday, Aug. 31
  • On a closed-to-autos Lake Shore Drive in Chicago
  • By the Active Transportation Alliance
  • Can ride the drive from 6:30 to 10:30 a.m.
  • Ride all or part of 30-mile loop, or ride it multiple times
  • See how it looks on this video, or what the wind sometimes is like in this video.

September

Let’s Ride, Illinois!

Harmon Hundred

  • Sunday, Sept. 7
  • By the Wheeling Wheelmen Bicycle Club
  • “Non-competitive scenic ride through Lake County”
  • Routes of 25, 50, 75 and 100 miles. Downloadable and on Ride with GPS.
  • Starts at Wauconda High School

North Shore Century

  • Sunday, Sept. 21
  • By the Evanston Bicycle Club
  • Routes from 25 to 100 miles
  • Starts on the Wilmette lakefront and runs north

Apple Cider Century

  • Sunday, Sept. 28
  • Popular ride (like 4,000 riders) out of Three Oaks, Michigan
  • Routes of 15, 25, 37, 50, 62, 75, or 100 miles

October

Tour de Proviso

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Comments

  1. Hi Neil,

    Thanks for another great issue of your blog. I am in the process of finalizing the date of our Ramble ride, which will likely be Sunday, June 7. If I let you know once it is finalized will you add it to your list of rides for 2026? Thanks

    Mitch Jones
    Ramble Chair
    BCLC

    Reply

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