I grew up running in the Chicago area and ran my first trail race as a college student in central Illinois on a bit of a whim.
What I figured was some kind of fast training run on rural dirt roads turned out to be an exhilarating, 7.5-mile race on mildly rolling singletrack that meandered through the trees, around small ponds and along a smooth flowing river in the Kickapoo State Recreation Area. I came to the quick and sudden realization that trail running was a whole different type of endurance fun.
What I’m here to say is that the Midwest doesn’t get nearly enough credit for its great trail running opportunities. There might not be big mountains in the Midwest, but there is an embarrassment of beautiful, accessible, and often surprisingly stunning (and challenging) terrain that will humble anybody from anywhere: rolling grasslands, deep sandstone canyon systems, glacier-carved moraine country, relentless hardwood ridgelines, raw, rocky shorelines, and impressive towering bluffs.
Plus, the trail running community in the Midwest is as tight-knit and welcoming as any in the country, and the summer racing calendar is loaded with races of all distances—including fun and festive 5Ks and 10Ks, competitive trail marathons, challenging 50-milers, legitimate 100-mile sufferfests, timed multi-hour events, and quirky-fun backyard ultras.
What follows is a selection of just some of the great Midwest trail running races that deserve your attention this summer. (If you have more suggestions and story ideas about Midwest trail running, please drop me a line at bmetzler@ultrasignup.com.)
In addition to the great Midwest races described below, be sure to check out these races, too: Kettle Moraine Endurance Races (June 2027, La Grange, Wisconsin), The Strawberry Solstice Run (June 20, Prairie du Chien, Wisconsin), Dawn to Dusk Endurance Run (June 27-28, Valders, Wisconsin), Akron Trail Marathon (July, 11, Akron, Ohio), Pinetum Mind Games Endurance Event (July 17, Dixon, Illinois), Quail Ridge Farm Backyard Ultra (July 18, Albion, Illinois), Lake McBride Trail Races (July 18, Solon, Iowa), Madder than a Wet Hen 5K (July 25, Charleston, Illinois),
Buckeye Moon Trail Runs (Aug. 8, Lewis Center, Ohio), White Oak Fest 5K (Aug. 8, Dodgeville, Wisconsin), Mines of Spain Trail Races (Aug. 8, Dubuque, Iowa), Bad Dawg (Aug. 15, Waynesville, Missouri), Camden Trail Races (Aug. 22, Lynd, Minnesota), Gristmill Grind, Wiley Canyon Ultra (Aug. 29, Lexington, Nebraska), (Sept. 5, Franklin Grove, Illinois), Temptation 200 Ultras (Sept. 5, Forest City, Illinois), SISU Backyard Ultra at Lake Rebecca (Sept. 5, Rockford, Minnesota), Hocking Hills Trail Run (Sept. 12, Logan, Ohio), Prairie on Fire Backyard Ultra (Sept. 12, Noblesville, Indiana), and the Cowboy 200 (Sept. 25-28, Norfolk, Nebraska).
Plus, you can search for more Midwest races in Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Nebraska, Missouri, Ohio, and Wisconsin or any place you plan to visit.
Dizzy GOAT 3/6/12 Hour Trail Runs
June 27, Omaha, Nebraska
3-hour, 6-hour, 12-hour timed runs
Timed events don’t always get the respect they deserve on race lists, but the Dizzy GOAT earns its spot with a well-designed 3-mile loop course at Chalco Hills Recreation Area in Omaha that rewards both competitive runners chasing big miles and first-timers using the forgiving format to dip a toe into trail ultrarunning for the first time. The 12-hour format can see the fastest runners hit 50, 60, or 70-plus miles, but the median finisher is someone doing something meaningful on their own terms — which is exactly the spirit the event is built on. Limited to 250 runners, it’s intimate, well-stocked, and one of the better arguments for why Nebraska’s trail community punches well above its weight.
Information and registration: Dizzy GOAT 3/6/12 Hour Trail Runs
Dark 2 Dawn Night Trail Races
June 27-28, Foristell, Missouri
9 hours, 6 hours, 10K
Dark 2 Dawn offers runners a chance to experience the trails in an entirely different way, beginning under the stars and continuing into the first light of morning at Indian Camp Creek Park west of St. Louis. The event features a 10K, as well as six-hour and nine-hour timed races held on a roughly 6.7-mile loop that blends open meadows with wooded singletrack, mostly on dirt with occasional rocky sections and gentle rolling terrain. The nighttime setting transforms an otherwise runnable course into a memorable adventure, where headlamp beams, nocturnal sounds, and the anticipation of sunrise create a uniquely immersive atmosphere.
Organized by Terrain Trail Runners, the race is known for its welcoming community vibe, overnight camping, sustainability initiatives, and enthusiastic volunteers who help make even the longest hours of the night feel a little brighter. Whether you’re tackling your first trail race in the dark or chasing mileage in the timed events, Dark 2 Dawn delivers a fun and refreshingly different ultrarunning experience.
Information and registration: Dark 2 Dawn Night Trail Races
Afton Trail Run
July 4, Afton State Park, Minnesota
50K, 25K
Founded in 1994, the Afton Trail Run is one of the oldest and most beloved trail races in the Twin Cities, and after 32 editions it has lost exactly none of its character. Afton State Park sits above the St. Croix River Valley near Hastings, and the course earns every foot of its reputation through relentless short, steep climbs up ravines and back down again — a style of trail running that’s harder on the quads than any single big mountain. The 50K draws a genuinely competitive field and has produced some memorable course records (the current 50K record of 3:26:52 was set in 2024), but the race is equally beloved by first-timers drawn in by the tight community and the spectacular river valley views. Hosted on UltraSignup by Rocksteady Running, one of Minnesota’s most respected race organizations.
Information and registration: Afton Trail Run
Eugene Curnow Trail Marathon
July 11, Duluth, Minnesota
26.2 miles
The Eugene Curnow Trail Marathon is one of Minnesota’s oldest and most cherished trail races, sending runners on a rugged point-to-point adventure from the Lake Superior Zoo in Duluth to Carlton. The 26.2-mile course traces a scenic stretch of the famed Minnesota Voyageur Trail, weaving through rocky singletrack, dense Northwoods forests, and nearly 3,000 feet of cumulative climbing. Along the way, participants are rewarded with expansive views of Duluth and Lake Superior and a memorable crossing of the iconic Swinging Bridge over the St. Louis River. Originally designed as a stepping stone to the Voyageur 50 Mile and later renamed in honor of trail-running pioneer Eugene Curnow, the race blends old-school toughness, stunning scenery, and a welcoming community spirit that has drawn runners back year after year for more than three decades.
Information and registration: Eugene Curnow Trail Marathon
Waugoshance Trail Run
July 11, Cross Village, Michigan
50K, 26.2 miles, 13.1 miles
Set along a spectacular stretch of the North Country Trail, Waugoshance showcases some of Michigan’s most underrated scenery. Runners traverse rolling bluffs overlooking Lake Michigan, coastal forests, inland lakes, and remote wilderness. With more than 90 percent singletrack, the race feels wild without becoming overwhelmingly technical. It’s the perfect northern Michigan summer adventure.
Information and registration: Waugoshance Trail Run
Cray Me a River Trail Races
July 17, Chilicothe, Illinois
100 miles, 50miles, 50K, 13.1 miles
Don’t let Illinois fool you—Cry Me a River packs a surprising amount of climbing into its wooded loops along the Illinois River bluffs near Peoria. Held at Camp Wokanda, the event offers distances ranging from a half marathon to 100 miles, with the longest race dishing out an eye-opening 18,500 feet of elevation gain through steep ridges, shaded forests, and relentless rolling terrain. Summer heat and humidity often become as formidable an opponent as the course itself, turning the race into a true test of patience, grit, and endurance. Despite its toughness, CMAR retains a distinctly Midwestern vibe, with enthusiastic volunteers, welcoming aid stations, on-site camping, and a tight-knit trail community that makes even first-timers feel like regulars. It’s equal parts sufferfest and summer camp—and one of the Midwest’s most underrated ultrarunning experiences.
Information and registration: Cry Me a River Trail Races
Minnesota Voyageur Trail Ultramarathon
July 25, Carlton, Minnesota
50 miles
One of the oldest trail ultras in the country, the Minnesota Voyageur has been sending runners from Carlton through Jay Cooke State Park to Duluth and back since 1982. The out-and-back course follows rough, rooted woodland trails northeast before climbing to sweeping overlooks above Lake Superior and the iconic Swinging Bridge over the St. Louis River — some of the most dramatic scenery in the Midwest, and it earns it on the way there. At 50 miles on genuine North Shore terrain, the Voyageur is a legitimate proving ground and a right of passage for Minnesota ultrarunners, but it also draws runners from across the country who understand what 43 years of race history means. A small but mighty community of volunteers keeps the course stocked and the culture warm.
Information and registration: Minnesota Voyageur Trail Ultramarathon
Oakadoke Trail Runs
Aug. 1, Valparaiso, Indiana
18 miles, 9 miles, 4 miles
Set amid the winding Creekside Trails near Valparaiso, Oakadoke highlights the unexpectedly engaging terrain of northwestern Indiana. The courses traverse shaded singletrack, snaking switchbacks, rolling hills, and a series of picturesque bridge crossings over Salt Creek. There may not be towering peaks on the horizon, but the constantly changing terrain and technical footing demand attention from start to finish. The race is also celebrated for its warm, welcoming atmosphere and festive post-race gathering that reflects the strong sense of community within Indiana’s trail-running scene.
Information and registration: Oakadoke Trail Runs
Badger Trail Races
Aug. 1-2, Belleville, Wisconsin
100 miles, 100K, 50 miles, 50K, 26.2 miles, 13.1 miles
The Badger Trail Races by Ten June Miles Racing are rail-trail racing done right. The course runs along the Badger State Trail from Belleville, Wisconsin up to Orangeville, Illinois on the Jane Addams Trail—a scenic, soft-surface corridor through rolling farm country with trestle bridges and a genuine sense of wide-open Midwest distance. The 100-miler starts August 1 with the shorter distances following on August 2, and the generous cutoffs make this a welcoming race for first-timers while the Badwater 135 qualifier status keeps it serious for veterans. The signature finishing hardware—a hand-tooled belt and the coveted Badger Buckle for 100-mile finishers—has become legendary in the region, and five-time finishers earn a “500 Mile Megabuckle” that takes the tradition to another level. (Also, the Badger 100 has been acknowledged as an official qualifier of the Badwater 135.)
Information and registration: Badger Trail Races
Marquette Trail 50
Aug. 14-15, Marquette, Michigan
50 miles, 50K, 1 mile
The Marquette Trail 50 has earned a reputation as the Upper Peninsula’s premier trail-running event, showcasing the rugged beauty and surprisingly technical terrain surrounding the southern shore of Lake Superior. Held on the renowned Noquemanon Trail Network, the race sends runners across rocky ridgelines, twisting forest singletrack, exposed granite slabs, and root-covered descents that demand constant focus and nimble footwork.
A relentless sequence of short, punchy climbs and descents gradually wears on the legs, making the course feel tougher than its elevation profile might suggest. Yet the challenge is balanced by spectacular scenery, including dense Northwoods forests, overlooks of Lake Superior, and the distinctive rock formations that define Michigan’s Upper Peninsula. Just as memorable is the enthusiastic local support: Marquette’s vibrant outdoor community embraces the event with contagious energy, creating an atmosphere that feels equal parts race, reunion, and celebration of the region’s trail culture. For runners looking to combine a serious athletic test with a quintessential Great Lakes adventure, few Midwest races offer a more complete experience.
Information and registration: Marquette Trail 50
Run the Hawk Trail Run
Aug. 22, Middleton, Wisconsin
12 Hour, 6 Hour, 3 Hour + Kids Fun Run
This timed event packs a serious punch onto a compact ski hill course. Each lap includes steep climbs beneath the historic Blackhawk Ski Club jump and through towering pines. The relay option adds a festive feel, while solo runners test their endurance over 3, 6, or 12 hours. Set in the rugged, unglaciated landscape in southwestern Wisconsin, the Driftless Area is defined by steep, forested bluffs, deeply incised river valleys, and cold, spring-fed streams. Unlike much of the Midwest, it was bypassed by the last Ice Age glaciers, leaving behind none of the glacial “drift”—the gravel, sand, and silt deposits that blanket much of the surrounding region.
Information and registration: Run the Hawk Trail Run
Shawnee Hills Trail Races
Aug. 22-23, Ozark, Illinois
100K, 50K, 25K, shorter options
Southern Illinois is one of the most underrated trail running destinations in the country, and the Shawnee Hills Trail Races make the strongest possible case for that argument. Based out of Camp Ondessonk in the heart of the Shawnee National Forest, the course winds through sandstone canyon systems, past towering rock formations, and alongside some of the most dramatic waterfalls in the Midwest — including Pakentuck Falls, the tallest free-falling waterfall in Illinois, and Jackson, Horseshoe, and Cedar Falls. The figure-eight loop course is roughly 80 percent singletrack on dirt trails through oak-hickory and maple-beech forest, and it’s the kind of terrain that surprises people who only know Illinois as flat farm country. For anyone who grew up running roads in this part of the state and never knew this terrain existed. Consider yourself in the know now.
Information and registration: Shawnee Hills Trail Races
Midwest States 100
Aug. 29-30, Chequamegon-Nicolet National Forest, Wisconsin
100 miles, 100K, 50K
This is the grassroots trail race that serious Wisconsin trail runners whisper about—a small-field, intentionally low-key event run on a lightly traveled section of the Ice Age Trail inside Chequamegon-Nicolet National Forest, one of the largest national forests east of the Mississippi. The majority of the course follows the Ice Age Trail, a 1,000-mile National Scenic Trail carved by ancient glaciers across rocky terrain, open prairies, and deep forest with lakes appearing regularly around nearly every bend. The race has a community-built feel that bigger events can’t replicate, and the option to stop at the 100K turnaround or continue on for the full 100 speaks to the kind of race direction that trusts runners to know their own limits.
Information and registration: Midwest States 100
Mindy Creek Trail Races
Aug. 29, St. Croix Falls, Wisconsin
26.2 miles, 13.1 miles, 10K
Mindy Creek Trail Races delivers a little bit of everything in an approachable, low-key package that perfectly captures the spirit of Midwest trail running. Held near St. Croix Falls, Wisconsin, just south of the Minnesota border, the race sends runners through a diverse mix of wooded singletrack, gravel paths, creek crossings, bridges, and gently rolling terrain that keeps the experience engaging without becoming overwhelming. The trails are scenic and varied, winding through forests and along the picturesque St. Croix River Valley, offering plenty of natural beauty along the way. Unlike some of the region’s larger marquee events, Mindy Creek maintains an intimate, community-driven atmosphere where volunteers know your name and post-race conversations linger long after the finish. For runners seeking a relaxed late-summer race that balances challenge, scenery, and small-town hospitality, Mindy Creek is one of the Midwest’s hidden gems.
Information and registration: Mindy Creek Trail Races
Superior Fall Trail Race
Sept. 11-12, Lutsen, Minnesota
100 miles, 50 miles, marathon
If you only run one race on this list, make it the Superior Fall Trail Race—and then clear your schedule for a week of recovery. Run on the Superior Hiking Trail along Minnesota’s North Shore above Lake Superior, the Superior Fall is the most technically demanding, scenically spectacular race in the Midwest by a considerable margin. The 100-mile course covers over 100 miles of rocky, rooted trail through boreal forest with enough climbing to make mountain runners from other regions take notice, and the views of the lake from the ridgeline are the kind that make you briefly forget how much your legs hurt. Hosted by Rocksteady Running (the same organization behind Afton and Zumbro), it’s a lottery entry race with fierce competition for spots — and every runner who’s ever stood at the start knows exactly why.
Information and registration: Superior Fall Trail Race
Hawk Hundred
Sept. 12, Lawrence, Kansas
100 miles, 50 miles, 26.2 miles
Put on by the Lawrence Trail Hawks—one of the most active and community-minded trail running clubs in the central Plains—the Hawk Hundred is the marquee trail race in Kansas and a genuine pilgrimage for Great Plains ultrarunners who’ve been quietly building one of the more underrated trail scenes in the country. The course runs a 25-mile loop on the technical, rolling singletrack of the North Shore Trails at Clinton State Park, looping around Clinton Lake with enough climbing, creek crossings, and tight turns through oak and cedar to make the word “Kansas” feel inadequate as a terrain descriptor. Four loops gets you the hundred, two gets you the 50, and the marathon adds a nature center out-and-back before sending you through one full circuit—which means runners across the experience spectrum have a reason to show up. The Lawrence Trail Hawks have built a race-day culture that’s welcoming without being soft, and the volunteer and crew support across all distances reflects a club that has been doing this long enough to know exactly what runners need at mile 60 in the Kansas heat.
Information and registration: Hawk Hundred
Pleasant Creek Trail Run
Sept. 12, Palo, Iowa
50K, 25K, 15K
Part of the No Coast Trail Series, the Pleasant Creek Trail Run has built a loyal Iowa following over more than a decade of low-key, well-organized racing on the equestrian trails of Pleasant Creek State Recreation Area near Palo. The course runs the outer loop of the equestrian trail—a rolling, grassy, and dirt mix with small water crossings that makes for fast times if conditions cooperate and character-building miles if they don’t. The Eastern Iowa Trail Alliance, a 501(c)(3) nonprofit, puts on the race with the kind of volunteer and community support that defines the best grassroots trail events. For Iowa runners building their trail racing resume, this is a home-state staple worth returning to year after year.
Information and registration: Pleasant Creek Trail Run
Porkies Wilderness Races
Sept. 19, Ironwood, Michigan
50 miles, 13.1 miles
The Porkies Wilderness Races take runners into one of the most genuinely remote trail environments in the entire Midwest—Porcupine Mountains Wilderness State Park in Michigan’s Upper Peninsula, a 60,000-acre expanse of old-growth forest, cascading waterfalls, rocky Lake Superior shoreline, and more than 90 miles of trail including a stretch of the North Country National Scenic Trail.
The 50-mile single-loop course was designed explicitly not for speed or comfort, but to put runners as deep into the wilderness as possible—steep climbs, technical descents, long stretches of muddy, rooted trail, and hours of night running in conditions that feel genuinely remote rather than just scenically inconvenient. Crew and pacer access is limited to a handful of designated points, which means runners spend long chunks of time alone with the forest, the ridgelines, and the sound of water—which is either exactly what you signed up for or a wake-up call about what you signed up for. For trail runners who’ve checked the boxes at every well-organized regional race and are looking for something rawer and harder to categorize, the Porkies is the answer.
Information and registration: Porkies Wilderness Races
Tuscazoar Endurance Race
Sept. 5, Dover, Ohio
100 miles, 75 miles, 50 miles (day and night), 25 miles (day and night)
The Tuscarawas River Valley of eastern Ohio is quiet trail country—the kind of place where you can run for hours without seeing much besides hardwood forest, rolling terrain, and the occasional limestone creek bottom. The Tuscazoar Endurance Race is built for that kind of running: deliberate, scenic, and honest about what it is. The race draws a regional crowd of Ohio trail runners who know this terrain well and a growing number of out-of-staters discovering that the eastern part of the state has more to offer than most trail running maps suggest. If you’re looking for a late-August long effort in atmospheric Ohio country with a field that feels like a community rather than a crowd, Tuscazoar belongs in the conversation.
Information and registration: Tuscazoar Endurance Race
East Fork Trail Runs
Sept. 12, Bethel Ohio
100 miles, 100K, 50K, 15K
Southwest Ohio finally has a hundred-miler it calls its own, and East Fork State Park—just 25 miles east of Cincinnati—turns out to be exactly the right place to build one. The course loops counterclockwise around William H. Harsha Lake on roughly 33 miles of rolling trail per loop, threading through mountain bike trail, hiking singletrack, a stretch of the Steve Newman Worldwalker Perimeter Trail, and a particularly memorable section through a pine forest with a waterfall that earns a genuine double-take at any hour of the day or night.
Runners will cross several creeks along the way, which feel less like obstacles and more like gifts by the time late summer heat settles in. The 100-miler is three loops, the 100K is two, and the 50K gets you one full circuit of terrain that’s more varied and technically interesting than most people expect from this corner of Ohio—which is, at this point, the recurring theme of trail running in this region.
Information and registration: East Fork Trail Runs
O’Brien Trail Races
Sept. 26, Marine on St. Croix, Minnesota
50K, 25K, 10K, 5K
As a late-summer race, the O’Brien Trail Runs carry a particular energy—the feeling of a season winding down, of one last chance to put in a big effort before the calendar turns. For runners chasing a first ultra finish, it’s a welcoming venue with enough challenge to feel earned. For those building out a late-summer racing schedule or exploring a new corner of the Midwest trail scene, it’s a reminder that world-class trail running doesn’t require mountains or coastlines—just good land, good trails, and a community that knows how to put on a race. The O’Brien Trail Runs are a fitting close to the Midwest summer trail season, and they make a strong case that the region’s trail running culture runs every bit as deep as the river valley it calls home.
The rolling terrain of William O’Brien State Park is both beautiful and deceptively challenging, the kind of course that encourages steady, controlled pacing early before quietly extracting its toll in the final miles, when the climbs feel just a little longer and the descents a little steeper than they did at the start. The park weaves together open prairie grasslands, dense hardwood forest, and scenic bluffs overlooking the St. Croix River Valley—a landscape that shifts dramatically from one mile to the next and rewards runners who pay attention to what’s underfoot.
Information and registration: O’Brien Trail Races
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