The starting stretch of the route curves between Illinois’ golden cornfields to link Chicago in the north with St Louis in the south. Both dazzle with sky-high architecture, from Chicago’s stratosphere-bothering Willis Tower to St Louis’ 192-metre Gateway Arch, but the two cities are united by their love of live music. These plains were once home to legends of the 20th-century music scene like Miles Davis, Scott Joplin and Tina Turner, and the tradition is just as strong today. Catch a jazz show in downtown Chicago or a blues night in St Louis and transport yourself back to a time when the music was raw, the drinks were cheap and the dancing was scandalous.
Next up is Missouri, as the road takes a 300-mile meander through the lowlands. If you’re keen to get off track and explore the wilds, this is the place to do it. The rolling Ozark Mountains are packed with opportunities for hiking and camping, and you’ll also find some of Route 66’s oldest tourist attractions, including the Meramec Caverns – the most over-the-top, underground cave experience out there, and reputedly a one-time hangout for notorious outlaw Jesse James. The 90 -minute tour covers more than a mile of subterranean scenery and treasure hunting.
Route 66 slices across the southeast corner of Kansas for a blink-and-you’ll-miss-it 13 miles. It’s a short stretch, but one of the best preserved on the entire route, with original signage and roadside advertising, and buildings that date back to the ’20s.
The Sooner State has played home to Native American tribes like the Kiowa, Apache and Comanche, and you can explore their heritage each June at the Red Earth Festival in Oklahoma City, where Native Americans celebrate their culture through dance, crafts and performing arts. These days OKC, as the locals know it, is far more than a cow town, but the cowboy life can be explored in depth at the National Cowboy & Western Heritage Museum.
As you head outstate, stop off in El Reno, affectionately known as Hamburger City. Robert’s Grill, on South Bickford Avenue, has been serving them up since 1926, but to truly understand the burger obsession you need to visit in May, when the whole town gets together to cook one of the world’s largest hamburgers, a 750-pound behemoth that’s the centrepiece for an all-day burgerfest.
Route 66 crosses just the northernmost tip of the Lone Star State, but in an area the size of Texas, that’s still a considerable distance. The road snakes through ghost like old cowboy towns like McLean (where you can still get a good steak – this is Texas, after all), and onwards to Amarillo. Make sure to stop on Western Avenue to pickup some antiques and kitsch cowboy memorabilia, and don’t miss the Big Texan Steak Ranch. Amarillo can claim to be the beef-producing capital of the world; the steaks are beautifully fresh and of a size in keeping with the state’s dimensions.
Buddy Holly may have been born over the state line in Texas, but it was New Mexico that turned him into a star. The bespectacled rocker recorded That’ll Be The Day and more at Norman Petty Recording Studios in Clovis, and you can still tour the famous studio. Just make sure to call and make an appointment-first. Outside of Clovis, the state’s open roads and cactus-dotted desert make for an exhilarating drive. As well as glitzy highlights like the Route 66 Casino in Rio Puerco, look out for Lightning Field, a land art installation by Walter De Maria made up of 400 steel poles designed to attract lightning strikes. If you’re lucky enough to pass during a storm, the sight is electrifying.
The Grand Canyon State’s big draw is obvious, and the route provides you plenty of opportunities to see the world’s most famous hole in the ground. To truly take in its grandeur, make a few diversions and try to see it from different angles, and at different times of day. Don’t forget to nip over the border to Las Vegas, either. Nevada’s Sin City is as thrilling, fun and in-your-face as its reputation suggests.
The Sunshine State’s stretch of the route is the most varied, and possibly the most scenic, with the barren but beautiful Mojave Desert melting into densely forested valleys and clean white beaches as you approach your final stop of Los Angeles. After the small towns of the last 2,000-plus miles, the mass of LA may come as a shock, but don’t neglect the huge amount to do and see. As well as Hollywood Boulevard and sunset strolls across Venice Beach, the city’s museums are world class, particularly the Los Angeles County Museum of Art, which owns a giant collection of European, American and Asian pieces. Finish at Route 66’s traditional endpoint, the pier at Santa Monica, and sip a cool cocktail as you dip your toes in the sea. After the road trip you’ve been on, you might just deserve it.