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MOTHER ROAD

The Herald

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July 08, 2026

HANNAH STEPHENSON and her daughter celebrate 100 years of Route 66 and discover quirky giants, dazzling diners and classic cars on the first section of the road

- HANNAH STEPHENSON

IF you love the open road, Americana, neon, retro murals, classic cars and carb-heavy historic diners, you'll need at least three weeks to enjoy Route 66 - the most famous road trip of them all - in its entirety.

In the Mother Road's centennial year, historic towns in the 2,448 miles over the eight states it crosses - from the skyscrapers of Chicago, Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico and Arizona to the sunny Californian pacific pier of Santa Monica - are holding their own celebrations, from car rallies and museum exhibitions, to 100th anniversary drone shows and community festivals.

But if your time is limited it’s easy to just do part of the route and I’ve opted for a city/Route 66 combo exploring the first leg from Chicago, Illinois to St Louis, Missouri, on a girls’ road trip with my daughter, Grace, a Gen-Z-er keen to temporarily step out of her digital-driven age and into a freedom-filled road of vintage Americana.

Route 66 was created in 1926 to stimulate economic growth via a direct, continuous commercial highway between the towns of the industrial Midwest and the agricultural Southwest, but also served the Great Migration of African Americans venturing to the Midwest after fleeing the Deep South. At the time, Chicago was considered a key gateway in the east for travellers heading west.

From the 1920s to the 1950s, as the automobile industry flourished, dozens of repair garages, tyre suppliers and car dealers set up shop along the route, along with motels and diners looking for passing trade.

While the Route 66 was decommissioned in 1985 and replaced by the quicker, more direct Interstate 55, travellers can follow the old historic route to see the highlights - over 90% of the original 301 miles in Illinois is still driveable.

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