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Cruising Route 66

America’s iconic Route 66 isn’t just for backpackers and neon-snappers. The classic road trip is also flush with cultural and artistic finds, writes Marie Barbieri.


Grab the RV and travel the Mother Road.

By the shores of Lake Michigan at 5.07am, I stand before ‘The Bean’ until the crack-of-dawn sun projects me onto Chicago’s skyscrapers. Cloud Gate, Sir Anish Kapoor’s 100-tonne stainless-steel sculpture theatrically mirrors the city, until I walk beneath its concave belly, where warped reflections turn the artwork abstract.

Chicago is the starting point for Route 66, an epic 3,940-kilometre road trip spanning eight states from Illinois in the Midwest, to California (Santa Monica) on the Pacific Coast. While the hallowed highway is a showreel of fast food and supersized statues, it also hides a trove of historical finds and cultural curios. In the lead-up to November 2026, when The Mother Road (so described in John Steinbeck’s The Grapes of Wrath) celebrates its centenary, I slowed to cruising speed to find some of its lesser-known treasures.

Illinois

From modern art to ancient artefacts, Illinois is a state of many faces. Cahokia Mounds World Heritage and State Historic Site in Collinsville preserves the vestiges of an ancient Mississippian civilisation. The pre-Columbian Native American settlement was home to an agricultural chiefdom society. Wandering the archaeological site’s wetland-surrounded earthen mounds, I pause by a 30-metre-tall grassy knoll. Named Monks Mound, the site hides ancient, terraced gardens that were once tended by Trappist monks.

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