Stop #8 in our “run every run club in Chicago” series, and this one’s got it all right there in the name: Casual Trails.
Casual Trails
They’re a mostly trail-running crew, but don’t let the “city-based” part fool you, this group shows up. They run trails together, they show up at races together, and yeah, they still do city runs too. We caught up with them out at their signature event: Hills Pay the Bills. Because if you’re trail running in Chicago, you know the one thing this city doesn’t hand you for free is vert. So Casual Trails just… makes their own. They post up at a hill, and everyone runs it up and down, over and over, together. It’s simple, it’s a little masochistic, and it’s honestly a great time.
Everyone we met was super, super friendly. This isn’t a group that’s just tolerating new people — they’re actively rooting for you. They lean hard into education, especially for folks who are newer to trail and ultra running, and they don’t just talk that talk. They’ll show up at your races. They’ll cheer you on. They’ll be in your corner.
Good for: the curious trail runner — someone newer to trail and ultra who wants a friendly, education-first crowd that genuinely wants to see you succeed.
Also good for: the experienced trail and ultra runner stuck in the city, who still wants to hang out with their fellow trail weirdos and get some vert in without leaving town.
Vibe: casual. Unserious. Unbothered. A genuinely good time.
Five out of five stars. We love Casual Trails.
CUSS Running hosts trail races, offers coaching, and spreads good vibes across Chicagoland. Everyone belongs on the trails, yes, even you
