Gravel & cycling events in Illinois

13 upcoming events in Illinois: gravel rides and races, road events, mountain bike and cyclocross.

October 2026

Big River Gravel Series

Gravel

October 31, 2026Registration Closed

Moline, IL

3.1 mi · $140 · 47 registered

Yellow Chip Road 2026

Gravel

October 31, 2026Registration Open

Kansas, IL

33 / 46 / 72 / 104 mi · $30–$40 · 25 registered

November 2026

Campton Cross - 2026 ChiCrossCup #6

CX

November 1, 2026Registration Open

Campton Hills, IL

45 registered

Bison or Bust! The Tertiary Trek: National Bison Day Ride to Midewin National Tallgrass Prairie

Gravel

November 7, 2026Registration Open

Chicago, IL

43 / 76 / 93 / 125 mi · Free · 4 registered

Groundhog PSI-Clocross Day 1 - 2026 ChiCrossCup #7

CX

November 7, 2026Registration Open

Woodstock, IL

33 registered

Groundhog PSI-Clocross Day 2 - 2026 ChiCrossCup #8

CX

November 8, 2026Registration Open

Woodstock, IL

32 registered

Quarry Cross at The Forge - 2026 ChiCrossCup #9

CX

November 22, 2026Registration Open

Lemont, IL

22 registered

December 2026

Montrose Beach CX - 2026 ChiCrossCup #10

CX

December 6, 2026Registration Open

Chicago, IL

6 registered

May 2027

White Squirrel Roubaix

Road

May 15, 2027Opens 1/1/2027

Olney, IL

12 / 31 / 62 mi · $30–$55

June 2027

Walk & Roll Chicago

Road

June 5, 2027Registration Open

Chicago, IL

9.3 mi · $20

Tour de Chi

Road

June 26, 2027Registration Open

Chicago, IL

150 mi · $30 · 1 registered

September 2027

HMFA’s Tour de Heartland Fundraiser

Road

September 11, 2027Opens 5/10/2027

Greenview, IL

12 / 17 / 45 mi · $35–$45

Dirtworx MTB Fest 2027

MTB

September 17, 2027Opens 6/1/2027

Findlay, IL