May
28
Unbound Gravel 2026
Born in 2006 as Dirty Kanza with just 34 participants, Unbound Gravel has evolved into the most prestigious gravel race…
Presented by Life Time Events
Midwest Events
40 upcoming events
May
30
Mohican Trail 100-50-Marathon 2026
The fifth-oldest ultra race in North America winds 95% on trail through the lush 5,000-acre Mohican Memorial State Forest. As…
Presented by UTMB World Series
May
31
Ride Across South Dakota 2026 (RASDak)
This week-long journey traverses South Dakota’s diverse terrain from the Black Hills to the Badlands, covering approximately 330 miles over…
Presented by RASDak
Jun
13
Horribly Hilly Hundreds 2026
The Horribly Hilly Hundreds lives up to its name as the Midwest’s most notorious cycling sufferfest. This Wisconsin classic draws…
Presented by Race Day Events
Jun
13
Pine Island Gravel Odyssey 2026
Formerly the Gold Rush Gravel Grinder, this South Dakota gravel event operates under special use permit in the Black Hills…
Presented by Ridge Rider Racing
Jun
13
Kettle Moraine 100 2026
This classic ultra marathon launched in 1996 serves as the second leg in the Midwest Grand Slam of Ultrarunning Series…
Presented by Western States 100 Qualifier
Jun
20
Solstice Gravel Grinder 2026
Now in its eighth year, the Solstice Gravel Grinder has evolved from a grassroots initiative into one of the Midwest’s…
Presented by Solstice Gravel
Jun
20
Lumberjack 100 2026
The Lumberjack 100 takes riders through 100 miles of Michigan’s Manistee National Forest, combining technical singletrack with the mental challenge…
Presented by Team Barry-Roubaix
Jun
27
Lutsen 99er 2026
The 99-mile mountain bike course starts at Lutsen Ski Resort in Minnesota’s Sawtooth Mountains, immediately challenging riders with a Category…
Presented by Life Time Events
Jul
18
Ride Across Indiana – RAIN 2026
This 160-mile journey across Indiana follows the historic National Road (US 40) from Saint Mary-of-the-Woods College in Terre Haute to…
Presented by Bloomington Bicycle Club
Jul
18
The Crusher 2026
The Crusher stands out for its ever-changing routes and raw, self-supported format that attracts gravel cycling purists. Starting as the…
Presented by 906 Adventure Team
Jul
18
RAGBRAI (Ride Across Iowa) 2026
Now in its 51st year, RAGBRAI stands as the longest recreational bicycle tour in the world, drawing thousands of cyclists…
Presented by Ventures Endurance Events
Jul
25
Burning River Endurance Run & Relay 2026
The Burning River Endurance Run follows the valley carved by the Cuyahoga River through Northeast Ohio’s most scenic terrain, including…
Presented by Western Reserve Racing
Aug
8
Ore to Shore (O2S) 2026
Michigan’s largest mass-start, point-to-point mountain bike race transforms Marquette County’s stunning terrain into an epic adventure from iron country to…
Presented by Team O2S
Aug
14
Marquette Trail 50 2026
This ultramarathon in Michigan’s Upper Peninsula delivers one of the most challenging and scenic trail running experiences in the Midwest.…
Presented by North Country Trail Association
Aug
19
Gravel Worlds 2026
Founded in 2010 by the Pirate Cycling League, Gravel Worlds has grown from a humble gathering of friends into Nebraska’s…
Presented by Pirate Cycling League
Aug
30
Dakota Five-O 2026
This 50-mile mountain bike race in early autumn delivers 90% singletrack through the Black Hills with over 6,500 feet of…
Presented by Ridge Rider Racing
Sep
4
Run Woodstock Hallucination 100 2026
Set against Michigan’s forest trails and lake country, the Run Woodstock Hallucination combines ’60s counterculture vibes with serious ultrarunning. This…
Presented by Western States 100 Qualifier
Sep
5
Glenwood Superbloom 2026
This women-only gravel cycling event has carved out a distinctive place in the Midwest cycling scene through its focus on…
Presented by Prairie Bloom Cycling Club
Sep
12
Ironbull Ultra Trail 2026
The Ironbull Ultra Trail transforms Rib Mountain State Park into an exceptional trail running experience with three challenging distances: 15K,…
Presented by Ironbull
Sep
12
Chequamegon MTB Festival 2026
Born in 1983 with just 27 riders on the American Birkebeiner ski trail, the Chequamegon MTB Festival has grown into…
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 surrounding areas come alive with the rhythmic hum of bicycle tires at this…
Presented by Evanston Bicycle Club
Sep
25
Birkie Trail Run 2026
The Icebug Birkie Trail Run transforms the legendary American Birkebeiner ski course into a challenging trail running experience through northwest…
Presented by American Birkebeiner Ski Foundation