Route 66, the quintessential American road trip spanning 2,500 miles from Chicago to Santa Monica, celebrates its 100th birthday in 2026. This year is the perfect time to discover the cultural icon, with a guide that steers you towards an authentic experience. The route, commissioned in 1926 and fully paved by the late 1930s, quickly attained legendary status despite not being the first or busiest long-distance highway.
The journey to cultural icon began with hundreds of thousands of farmers using it to reach California during the Dust Bowl, immortalised in John Steinbeck's 1939 novel 'The Grapes of Wrath', where he dubbed it the 'Mother Road'. After the Second World War, car ownership exploded and Americans discovered the road's bewitching desert landscapes, neon-lit motels and diners that symbolised classic road trip culture. By its decommissioning in 1985, it was ingrained in popular culture through songs and films.
Chicago is the traditional launchpad, with the ceremonial starting point on Adams Street near the Art Institute of Chicago. Before setting off, tradition dictates breakfast at Lou Mitchell's restaurant on W. Jackson Boulevard, serving westbound road-trippers since 1923. The menu offers classic diner fare, and staff hand out complimentary donut holes and Milk Duds while you wait. A recommended stay is the Silversmith Hotel Chicago Downtown, just three minutes' walk from Route 66.
Navigation is key: typing 'Route 66' into Google Maps is a major mistake, as the route is no longer one continuous highway but a patchwork of historic sections. Following 'Historic Route 66' signs leads to the most compelling sights and scenery, avoiding interstates that replaced large sections. The ideal timeframe for the journey is two weeks, or 15 days, allowing leisurely enjoyment of the road's delights.
