Gravel & cycling events in the Midwest, June 2027

17 events in the Midwest in June 2027.

Gordon Pine Barrens 50

• Gravel

Sat, Jun 5, 2027Open

Gordon, WI

25 / 50 mi · $45 · 16 registered

Walk & Roll Chicago

• Road

Sat, Jun 5, 2027Open

Chicago, IL

9.3 mi · $20

Fort4Fitness Spring Cycle

• Road

Sat, Jun 5, 2027Opens Dec 29

Fort Wayne, IN

22 / 36 / 50 / 63 mi +1 more · $30–$35

MCMBA MILFORD BIKE FEST AND TRAIL CHALLENGE

• Road

Sat, Jun 5, 2027Closed

Milford, MI

Happy Soles 5k Run/Walk/Bike & Virtual Challenge

• Road

Sun, Jun 6, 2027Opens Dec 6

Taylor, MI

3.1 mi · $35

Refo24

• MTB

Sat, Jun 12, 2027Opens Jan 1

Suamico, WI

Pedal Putnam 2027

• Road

Sat, Jun 12, 2027Opens Nov 25

Greencastle, IN

13 / 43 / 62 mi · $30–$70

Cogs and Kegs

• Road

Mon, Jun 14, 2027Opens Mar 19

Birmingham, MI

10 / 30 mi · $45–$55

2027 - National 24 Hour Cycling Challenge (N24HCC)

• Road

Sat, Jun 19, 2027Open

Hastings, MI

2 registered

Horribly Hilly Hundreds

• Road

Sat, Jun 19, 2027Opens Feb 6

Blue Mounds, WI

Loop the Lake - A bike ride to benefit our lakes

• Road

Sat, Jun 19, 2027Open

Madison, WI

Pedal Across Lower Michigan (PALM)

• Road

Sat, Jun 19, 2027Opens Jan 1

TBD, MI

325 mi · $210

Michigan's Coast to Coast Gravel Grinder 204-Miler & Coast Loop 100-Miler

• Gravel

Sat, Jun 26, 2027Open

Au Gres (204 start) to Ludington (204 and 100 finish), MI

100 / 204 mi · $70–$190 · 93 registered

Tour de Chi

• Road

Sat, Jun 26, 2027Open

Chicago, IL

150 mi · $30 · 1 registered

KeyBank Gran Fondo

• Road

Sat, Jun 26, 2027Open

Grand Rapids, MI

8.9 / 20 / 38 / 81 mi · $49–$209

Flat 50 (Adams County, IN)

• Road

Sat, Jun 26, 2027Opens Dec 16

Berne, IN

50 mi · $35

Lutsen 99er

• MTB
• Gravel

Sat, Jun 26, 2027Opens Dec 1

Lutsen, MN

31 / 47 / 60 / 97 mi · 5,105 ft