Gravel & cycling events in the Midwest, September 2027

9 events in the Midwest in September 2027.

Firefly Trail Festival

• MTB

Sat, Sep 4, 2027Open

Fort Wayne, IN

6.2 / 12 / 19 mi · $20

HMFA’s Tour de Heartland Fundraiser

• Road

Sat, Sep 11, 2027Opens May 10

Greenview, IL

12 / 17 / 45 mi · $35–$45

PEDALS

• Gravel
• Road
• MTB

Sun, Sep 12, 2027Opens Dec 31

Cannonsburg, MI

10 / 20 / 32 / 62 mi · $65

Dirtworx MTB Fest 2027

• MTB

Fri, Sep 17, 2027Opens Jun 1

Findlay, IL

Marji Gesick

• MTB

Fri, Sep 17, 2027Open

Ishpeming, MI

15 / 50 / 100 mi · $150–$195

Mora Bike Tour and GraveLoppet Race

• Gravel
• Road

Sat, Sep 18, 2027Open

Mora, MN

4.5 / 25 / 50 / 100 mi · $10–$50

Chequamegon MTB Festival

• MTB

Sat, Sep 18, 2027Opens Dec 1

Hayward, WI

16 / 40 mi

IWP Ride Against Suicide 2027

• Road

Wed, Sep 22, 2027Opens Jan 15

Forest Lake, MN

73 / 86 / 300 mi · $100

Fall Color Festival

• MTB

Sat, Sep 25, 2027Opens Feb 28

Whitewater, WI

5 / 13 / 18 / 31 mi · $25–$35