Historic Highway Hustle - Rt. 66

Experience Route 66 like never before with an expanded adventure that blends athletic challenge, rich history, and roadside Americana. The Historic Highway Hustle – Rt. 66, a one-of-a-kind series of 6.6K races set along some of Illinois’ most iconic Route 66 landmarks, invites runners to step into the past as they take on a trio of immersive events, each celebrating a legendary stop along the Mother Road. Feel the adrenaline as you weave through the imposing grounds of the Old Joliet Prison, where towering limestone walls echo with stories of another era. Let your stride fall in rhythm with the quirky, retro charm of the Gemini Giant in Wilmington—one of the highway’s most photographed icons. Then soak in the vintage ambiance of Ambler’s Texaco Gas Station in Dwight, an immaculately preserved slice of Americana that transports you to the golden age of American road travel.

Every race offers participants collectible swag, lively local entertainment, and the chance to explore three communities that proudly keep the spirit of Route 66 alive. Join fellow runners, history lovers, and adventure seekers as you journey through time, town by town. The Historic Highway Hustle isn’t just a series of races—it’s a celebration of culture, endurance, and the open road. Lace up and make your mark on history!

Join fellow runners on May 3, 2026 for the Historic Highway Hustle - Rt. 66. It's a fantastic 6.6K featuring a flat and fast course in Joliet.