Jun
13
Horribly Hilly Hundreds 2026
The Horribly Hilly Hundreds 2026 is the Midwest’s premiere sufferfest and is worth putting on your season’s bucket list. Chosen…
Presented by Race Day Events
Midwest Events
44 upcoming events
Jun
13
Pine Island Gravel Odyssey 2026
The Pine Island Gravel Odyssey 2026 was formerly known as the Gold Rush Gravel Grinder and is rated by Strambecco…
Presented by Ridge Rider Racing
Jun
13
Kettle Moraine 100 2026
This classic ultra marathon, the Kettle Moraine 100 2026 Endurance Trail Races was started in 1996. It is the second…
Presented by Western States 100 Qualifier
Jun
20
Solstice Gravel Grinder 2026
The Solstice Gravel Grinder 2026 is an annual gravel cycling event held in the southeastern region of Nebraska. Now in…
Presented by Solstice Gravel
Jun
20
Lumberjack 100 2026
The Lumberjack 100 2026 Mountain Bike event is an annual race that draws experienced mountain bikers from all levels, including…
Presented by Team Barry-Roubaix
Jun
27
Lutsen 99er 2026
The Lutsen 99er 2026 movement continues high above the shores of beautiful Lake Superior. This 99-mile course (69-, 49-, and…
Presented by Life Time Events
Jul
18
The Crusher 2026
Held annually in Munising, Michigan, The Crusher 2026 offers a unique blend of adventure, community, and a true test of…
Presented by 906 Adventure Team
Jul
18
Ride Across Indiana – RAIN 2026
The Ride Across Indiana – RAIN 2026 is a premier cycling event that encapsulates the spirit of adventure, endurance, and…
Presented by Bloomington Bicycle Club
Jul
18
RAGBRAI (Ride Across Iowa) 2026
The RAGBRAI (Ride Across Iowa) 2026 is the Register’s Annual Great Bicycle Ride Across Iowa, an eight-day ride across the…
Presented by Ventures Endurance Events
Jul
25
Burning River Endurance Run & Relay 2026
The annual Burning River Endurance Run & Relay 2026, produced by Western Reserve Racing, offers 100-mile, 50-mile, and Marathon solo…
Presented by Western Reserve Racing
Aug
8
Ore to Shore (O2S) 2026
Ore to Shore (O2S) 2026 Mountain Bike Epic is touted as Michigan’s largest mass-start, point-to-point mountain bike race in the…
Presented by Team O2S
Aug
14
Marquette Trail 50 2026
The Marquette Trail 50 2026 in Michigan’s Upper Peninsula is an event that stands out for its challenging courses and…
Presented by North Country Trail Association
Aug
19
Gravel Worlds 2026
Gravel Worlds 2026 will celebrate its annual event and as a testament to the quality of the event, Lauf is…
Presented by Pirate Cycling League
Aug
30
Dakota Five-O 2026
In early autumn, the town of Spearfish, South Dakota, is overtaken by the Dakota Five-O 2026. This adrenaline-pumping mountain bike…
Presented by Ridge Rider Racing
Sep
4
Run Woodstock Hallucination 100 2026
Set against the backdrop of Michigan’s luscious forest, meandering dirt tracks, and the shimmer of a beach, the Run Woodstock…
Presented by Western States 100 Qualifier
Sep
5
Glenwood Superbloom 2026
The Glenwood Superbloom 2026 is a Women Only gravel cycling event is a thrilling and empowering experience that celebrates the…
Presented by Prairie Bloom Cycling Club
Sep
12
Ironbull Ultra Trail 2026
Ironbull Ultra Trail 2026 invites all trail runners to gather in Rib Mountain State Park for 3-course options at the…
Presented by Ironbull
Sep
12
Chequamegon MTB Festival 2026
An extremely popular event that attracts thousands of off-road enthusiasts, the 41st edition of the Chequamegon MTB Festival 2026 takes…
Presented by Life Time Events
Sep
19
Marji Gesick 50/100 2026
The 2026 event has not been confirmed yet… The Marji Gesick 50/100 2026 is one of the best long-distance endurance…
Presented by National Ultra Endurance Race Series (NUE)
Sep
20
North Shore Century 2026
In September, the streets of Evanston and its surrounding areas come alive with the rhythmic hum of bicycle tires at…
Presented by Evanston Bicycle Club
Sep
25
Birkie Trail Run 2026
Welcome to the heart-pounding Icebug Birkie Trail Run 2026, an exhilarating adventure set in the enchanting landscapes of northwest Wisconsin.…
Presented by American Birkebeiner Ski Foundation
Oct
10
Indiana Trail 100 (IT 100) 2026
The final leg of the Midwest Grand Slam of Ultrarunning and a qualifier event for the famed Western States 100,…
Presented by Ignite Trail Series
Oct
10
Ironbull Red Granite Grinder 2026
Winding its way through beautiful central Wisconsin is the Ironbull Red Granite Grinder 2026, a premier US gravel event rated…
Presented by Ironbull
Oct
17
Spotted Horse Gravel Ultra 2026
Nestled in the serene landscapes of St. Charles, Iowa, the Spotted Horse Gravel Ultra 2026 is more than a race;…
Presented by Relentless Events