Strambecco rates the best trail running events in the Midwest for 2025 based on various factors, including reputation, route quality, location, runner feedback, and the overall uniqueness of the event or race. Spanning Michigan, Wisconsin, Illinois, Kansas, Iowa, South/North Dakota, Nebraska, Indiana, and Minnesota, the Midwest terrain features of Strambecco’s best list is generally flat or rolling.
The Midwest is home to many prominent and well-organized events. Strambecco’s list of best trail running events in the Midwest 2025 includes events that are components or qualifiers for prestigious regional, national, and international race series, including the Midwest Grand Slam of Ultrarunning Series, Western States 100, and UTMB World Series.
Strambecco does not list every event. We strive to identify and review events that are special and noteworthy. If you have suggestions on other events we should consider or review, don’t hesitate to contact us here or send us a note at editors@strambecco.com.
The Glacial Esker Trail Race offers a unique timed loop format where participants choose between 6, 12, or 24-hour challenges on a 3.55-mile course through Chain O’Lakes State Park. This distinctive approach…
One of the oldest continuously-running ultras in the country, the Ice Age Trail 50 offers a uniquely diverse Wisconsin landscape that showcases the region’s glacial history. The course winds through dense deciduous…
The fifth-oldest ultra race in North America winds 95% on trail through the lush 5,000-acre Mohican Memorial State Forest. As the opening leg of the Midwest Grand Slam of Ultrarunning, Mohican has…
This classic ultra marathon launched in 1996 serves as the second leg in the Midwest Grand Slam of Ultrarunning Series and qualifies runners for the Western States 100. Beyond the signature 100-mile…
The Burning River Endurance Run follows the valley carved by the Cuyahoga River through Northeast Ohio’s most scenic terrain, including Cuyahoga Valley National Park, Summit Metro Parks, and Stow Parks. As a…
This ultramarathon in Michigan’s Upper Peninsula delivers one of the most challenging and scenic trail running experiences in the Midwest. The course tackles four prominent peaks through demanding single-track trails, rewarding runners…
Founded in 2010 by the Pirate Cycling League, Gravel Worlds has grown from a humble gathering of friends into Nebraska’s premier gravel celebration while maintaining its grassroots spirit. The event operates without…
Set against Michigan’s forest trails and lake country, the Run Woodstock Hallucination combines ’60s counterculture vibes with serious ultrarunning. This groovy weekend serves as the fourth leg of the Midwest Grand Slam…
The Ironbull Ultra Trail transforms Rib Mountain State Park into an exceptional trail running experience with three challenging distances: 15K, 25K, and 50K. What sets this event apart is its unique start…
The Icebug Birkie Trail Run transforms the legendary American Birkebeiner ski course into a challenging trail running experience through northwest Wisconsin’s glacial terrain. This event stands out for its unique course composition—80%…
Founded in 2013 as Indiana’s first 100-mile ultramarathon, this event has evolved into a world-class race that serves as both the final leg of the Midwest Grand Slam of Ultrarunning and a…
The Ignite Trail Marathon takes place on a challenging 13.1-mile loop through Chain O’Lakes State Park that runners complete twice. The course weaves through diverse terrain including rolling grass pastures, technical singletrack,…
