The Best Trail Races in Chicagoland (And Yes, Ours Are Obviously the Best)

Posted by the CUSS Running crew

Let’s be real for a hot minute – we’re obviously going to tell you that our Fancy Nonsense race on October 25th is the crown jewel of Chicago trail running. I mean, we’ve got 5-mile, 25k, and 50k options, plus enough good vibes to power the entire city grid. But here’s the thing: we’re not the only game in town, and that’s actually pretty damn awesome.

Why Grassroots Trail Running is the Real MVP

Before we dive into our favorite local sufferfests, let’s talk about why grassroots trail running is the unsung hero of our sport. These aren’t your massive, corporate-sponsored mega-races with $200 entry fees and porta-potties that smell like… well, you know. These are the races run by people who genuinely love this ridiculous sport we’ve all gotten ourselves mixed up in.

Grassroots races are where you’ll find aid stations stocked with actual food (not just gels that taste like sadness), race directors who know your name by your third race, and post-race parties that feel more like family reunions than corporate networking events. They’re the backbone of trail and ultra running, and they deserve your muddy shoes and your annual registration fee.

Our Top Picks for Chicago Area Trail Races

CUSS Running’s Fancy Nonsense (Obviously)

October 25th, 2025 | Chicago, IL | 5 miles, 25k & 50k

Look, we had to start with ourselves – it’s our blog! But seriously, Fancy Nonsense isn’t just a race; it’s a celebration of everything silly and wonderful about running through the woods. We’ve got distances for everyone from “I’m new to this trail thing” to “I’ve clearly lost my mind and want to run 50k.” Plus, our aid stations are legendary, our volunteers are the absolute best, and we promise the post-race vibes will make your Instagram followers jealous.

Universal Sole Races

These folks have been putting on quality trail races in our area for years, and they know their stuff. Universal Sole events are consistently well-organized, fairly priced, and attract the kind of runners who high-five strangers and share their snacks. They’ve got a variety of distances and locations throughout the year, making them perfect for building your racing resume or just getting out there to suffer beautifully with fellow trail nerds.

Lakefront 50k/50 Miler

If you’re looking to test your limits against Lake Michigan’s stunning (and sometimes brutal) backdrop, this is your race. The Lakefront series offers both 50k and 50-mile options, because apparently some people think 31 miles isn’t quite enough punishment. The flat, fast course is perfect for first-time ultra attempts or chasing that elusive PR, and running along the lakefront provides scenery that almost makes you forget how much your legs hurt. Almost.

Paleozoic 25k/50k

Named after an era when life was simpler (and probably involved less voluntary suffering), the Paleozoic races bring serious trail running energy to the Chicago area. With 25k and 50k options, these races attract runners who appreciate both geological humor and well-marked courses. The community at these events is tight-knit and welcoming, which is exactly what you want when you’re questioning all your life choices around mile 20.

Ornery Mule Racing & Des Plaines River Trail Race

Here’s a shout-out to our friends at Ornery Mule Racing who, while primarily regional race directors, have blessed the Chicago area with the Des Plaines River Trail race. This is a fantastic event with multiple distances that showcases some beautiful trail running right in our backyard. Ornery Mule knows how to put on a quality event, and the Des Plaines River Trail race is proof that sometimes the best races come from directors who’ve honed their craft across different regions. These folks understand that trail running is about more than just the miles – it’s about the experience, the community, and having a damn good time while your legs slowly revolt against your life choices.

The Golden Rule of Local Trail Racing

Here’s the thing about grassroots trail races: they only exist because passionate people pour their hearts (and often their own money) into making them happen. So here’s our plea – find a local race, run it, and then run it again next year. And the year after that. Make it a tradition.

These race directors aren’t getting rich off your entry fees. They’re doing this because they love our weird little community and want to give back. The best way to support them? Show up. Consistently. Bring friends. Volunteer when you can. Buy the t-shirt even if you already have 47 running shirts.

Why You Should Run Local (Besides the Obvious Reasons)

You’ll actually know people: Instead of being anonymous runner #4,847 in a sea of strangers, you’ll start recognizing faces, making friends, and building a genuine community.

The competition is real: Don’t let the smaller field size fool you – local races often attract seriously fast runners who just prefer the intimate atmosphere.

Your money stays local: Supporting grassroots races means supporting local trail access, conservation efforts, and the people who maintain the trails we all love to destroy our legs on.

Less stress, more fun: Smaller races mean easier parking, shorter lines, and more opportunities to chat with fellow runners instead of just surviving the logistics.

The Bottom Line

Chicago’s trail running scene is thriving, and it’s not because of one race or one organization (even though we’re pretty awesome). It’s because we have a community of race directors, volunteers, and runners who show up year after year to support each other’s crazy dreams and questionable life choices.

So mark your calendars, start training, and remember – the best trail race is the one you actually sign up for. Whether that’s our Fancy Nonsense (highly recommended, obviously), a Universal Sole event, or any of the other fantastic local races happening throughout the year, your legs will hate you and your soul will thank you.

Now quit reading blogs and go run some trails. Those trees aren’t going to high-five themselves.

Ready to join the CUSS Running community? Check out our race schedule, sign up for coaching, or just follow us for daily doses of trail inspiration and the occasional existential crisis about why we choose to run through the woods for fun.

Questions? Text us at 773-633-8986 or email ally@cussingrunner.com[/vc_column_text][/vc_column][/vc_row]