Gravel & cycling events in the Midwest, May 2027

12 events in the Midwest in May 2027.

The Bear 100

• Gravel

Sat, May 1, 2027Opens Jan 1

Laona, WI

18 / 31 / 61 / 103 mi · $0–$69

The Steel Dynamics Garbage Mountain Gravel Grinder

• Gravel

Sat, May 1, 2027Open

Terre Haute, IN

35 / 63 mi · $40

Mud, Sweat & Beers - The Lumberjack 17!!!

• Road
• MTB

Sat, May 1, 2027Opens Nov 30

Traverse City, MI

4 / 12 / 14 / 25 mi +1 more · $15–$70

Hungry Bear Gravel

• Gravel

Sat, May 8, 2027Open

Cable, WI

28 / 60 / 100 mi · $49 · 73 registered

Calvins Challenge 2027

• Road

Sat, May 15, 2027Open

Springfield, OH

7 / 16 / 50 / 100 mi · $45–$100

Custer’s Last Stand

• MTB

Sat, May 15, 2027Opens Jan 1

Augusta, MI

7.5 / 15 / 23 mi · $45

White Squirrel Roubaix

• Road

Sat, May 15, 2027Opens Jan 1

Olney, IL

12 / 31 / 62 mi · $30–$55

Red Eagle Gravel Grinder

• Gravel

Sun, May 16, 2027Opens Jan 1

Geneva, OH

12 / 23 / 44 mi · $50

American Triple-T Multisport Festival

• Road

Fri, May 21, 2027Open

Perrysville, OH

26 / 52 mi · $30–$40

2027 Mohican 100 Mile/100K/50K MTB Race OMBC

• MTB

Sat, May 22, 2027Open

Loudonville, OH

31 / 62 / 100 mi · $80–$180 · 153 registered

Dr. John Seaman Memorial 5k Run/Walk/Bike

• Road

Sat, May 29, 2027Opens Jan 29

Vicksburg, MI

12 mi · $40

KEJ: Gravel 2027

• Gravel

Sat, May 29, 2027

McArthur, OH

11 / 20 / 37 mi