The Ultimate Guide To Route 66

The Ultimate Guide To Route 66

Boss Hunting
Boss Hunting


Brand USA Vist The USA Logo

This article is part of a series celebrating Boss Hunting’s favourite corners of the United States. Click here to see more.

Route 66, the great American road trip, has long been immortalised by pop culture; and equally formed in the daydreams of travellers longing for a taste of freedom. You know, the kind you get when you’re throttling it down the highway, summer breeze whipping through your hair and hopping across the hardy roadside taverns of Arizona and New Mexico.

Starting from downtown Chicago and snaking to California’s Santa Monica Pier, Route 66 is a dream journey for many and a reality for a few. You’ll need to dedicate at least two weeks on the road; and as long as a month, if you want to do it justice. Yet the investment of your time and money is worth it for the USA’s most profound and exciting road trip.

John Steinbeck once famously used Route 66 as a metaphor for escape, loss, and the hope of a new beginning — dubbing it the “Mother Road” for its role in the USA’s changing cultural identity at the time. 

The drive, which opened in 1926 and has been an icon ever since, will take you through eight states — Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California — and around 20 major stops. Diverse landscapes, cuisines, cultures, as well as communities are given, offering up a legendary range of experiences threaded together by a 3,940-kilometre highway.

Below, you’ll find the quintessential stops that make driving Route 66 such a life-changing experience; one that will help you understand just why the USA prides itself on this arterial American icon.


The ultimate road trip starts on the shores of Lake Michigan, in the windy city of Chicago, in the USA’s midwest.

Spend a day or two getting all the logistics sorted while exploring what is consistently voted one of the country’s best big cities. Grab a bite at Girl & the Goat or, better yet, carb load with Au Ceval’s show-stopping burgers.

Maybe you’ll want to catch some live jazz at The Green Mill, browse the comprehensive Art Institute of Chicago, or just take an architectural tour of the Chicago River to enjoy some relaxation before the enormous undertaking ahead.

Gemini Giant and Springfield will be your first two stops. The former is most notable for its procession of oversized fibreglass statues called Muffler Men, which were originally used to advertise roadside businesses.

Springfield will be of more interest to history buffs, as this is where US President Abraham Lincoln was born and raised. You can visit his house on South Eighth Street, his eponymous library and museum, as well as his gravesite at Oak Ridge Cemetery.

Missouri & Kansas

Located 4.5 hours southwest of Chicago, St. Louis is Missouri’s second-largest city and your first major stop along Route 66. Get ready to bunker down for the night in the Mound city.

Pass through the emblematic Gateway Arch and splurge on a stay at the swanky Ritz-Carlton St. Louis. Head to Charlie Gitto and try the kitchen’s signature toasted ravioli. Or sample some Kansas-style BBQ at Pappy’s Smokehouse.

Before you leave the state, follow the signposts for Meramec Caverns. The 4.6-mile cave system in the Ozarks is home to some epic illuminated cave formations and is also one of Missouri’s best contributions to the USA’s spoil of natural wonders.

Kansas’s piece of Route 66 was actually the first to be paved, making it a historical part of the iconic route. The “tiny towns” of Galena, Riverton, or Baxter Springs are perfect pitstops for a  quick bite, while the Rainbow Bridge — built in 1923 over Bush Creek as a part of the historic old Route 66 — is well worth the quick detour. 

Oklahoma & Texas

Continue southwest for 6 hours, past the Mark Twain Forest, through Springfield, then onwards until you reach Oklahoma. The state is a big part of the experience, given it has more original sections of Route 66 than any others along the highway.

Clinton’s Route 66 Museum celebrates the fact proudly so drop in before landing in Tulsa, a city most known for its rich collection of Art Deco buildings. Stay in celebrity-favourite The Mayo Hotel and drive north to the town of Sperry the day after for the award-winning Buffalo’s BBQ. 

Texas doesn’t claim as much of Route 66 as one might assume, but you’ll still pass through a number of ghostly towns and roadside attractions in the Texas Panhandle region. Palo Duro Canyon is a must for nature lovers with its dramatic rock formations. Art lovers might prefer the eccentric Cadillac Ranch, a public art installation of 10 vintage Cadillacs wedged into the ground and covered with graffiti. 

Amarillo’s Big Texan Steak Ranch has been around since 1960 and is one of Route 66’s signature roadside diners. Hop off I-40 and get some protein in you before heading to New Mexico.

New Mexico

Tucumcari, roughly 1.45 hours drive west of Amarillo, will be your first step upon crossing the border into New Mexico.

Here is a town that prides itself on being Route 66’s most vibrant time capsule with offbeat 1950s diners, Art Deco motel signs, and large-scale murals embodying the Mother Road. 

You might want to stop by Santa Rosa for the Route 66 Auto Museum, but otherwise spend most of your time in New Mexico in the fascinating city of Santa Fe. The country’s oldest capital city also contains some of the USA’s oldest buildings, including the first house and first church. Give these a visit before browsing Canyon Road, where more than 80 galleries are carved into low, historic abode homes.

The multicultural city of Albuquerque is your tail-end of the New Mexico part of Route 66. Check into the atmospheric El Vado Motel on the edge of Old Town and spend a night or two exploring the city. New Mexico is the oldest wine-growing region in the USA, so you’ll want to visit Casa Rondena Winery, or stick closer to Downtown and try old-school steakhouse Antiquity Restaurant or the award-winning Campo at Los Poblanos.


Arizona means you’ve reached the last few days of your road trip but it’s worth saving some time to enjoy all the fascinating stops and detours. 

The most memorable is Petrified Forest National Park, the only national park on Route 66 and an easy 3-hour drive west of Albuquerque. The enchanting landscape features a prehistoric, fossilised forest so go for a hike and find the perfect view of the Painted Desert, Arizona’s most recognised badlands.

Also off I-40 is one of Arizona’s eeriest ghost towns, Two Guns, where you’ll find the skeletal remains of stone buildings, rogue tumbleweeds, roaming donkeys, and not much more.

Continue west for 1.45 hours and spend a night in Flagstaff to recharge. Outdoor activities are aplenty here but if you’re too exhausted, spend a night at Bespoke Inn and grab some dinner at fine-dining restaurant Atria. 

Stop by Williams and check into one of the town’s many retro diners and roadside motels, before heading off to Grand Canyon National Park the following day. The American icon isn’t officially part of Route 66, though the South Rim is only a short detour, so it’s worth the side quest. 

Prior to capping your time in Arizona off with a night in Kingman, might we suggest visiting the colourful town of Seligman for lunch at Gelgadillo’s Snow Cap? The quirky fast-food joint was built from scrap lumber in 1953 and feels like a proper movie set, complete with various memorabilia and classic American diner food. 

Kingman is the retro heart of Route 66, so spend a night or two here to reflect on your journey. Take your pick of a number of mid-range motels and have some fun at The Sundowner Saloon. If you want to fit in one more ghost town, then the charming enclave of Chloride City is only an hour’s ride from Kingman’s Downtown. Or you can go for a spot of fishing on Lake Mohave.

Finally, if you’ve got spare time, scoot on over to the historic town of Oatman and watch a staged shootout for some Old West flavour.


California is when you start to leave most of Route 66’s vintage components behind and edge towards Santa Monica pier, which is a 5.5 hour drive away.

One of your first stops will be Needles, less than an hour’s drive from Kingsman. Save this one for lunch and grab a bite at the kitschy Wagon Wheel Restaurant. After a further 2.5 hours Barstow will be up next, so either stop to check out the Mother Road Museum or continue on for dinner at the classic Emma Jean’s Cafe in Victorville.

San Bernardino has some of the most authentic Mother Road atmosphere; stop by here and check in to the charming Wigwam Motel for something a bit different. Alternatively, keep going to the penultimate stop: Pasadena.

The city, which is part of greater Los Angeles, is a great place to stay so check into the five-star hotel, The Langham Huntington, and choose either Italian at Union Restaurant or French at Perle Restaurant for dinner.

Leaving Pasadena, you’ve got a 40-minute drive to reach Santa Monica pier which is where you’ll find the “End of the Trail” sign to signify the official end of Route 66. You deserve to take a moment; not many people have conquered the entire Mother Road in one fell swoop. 

Fortunately, Santa Monica has plenty to cradle exhausted travellers. Spend a full day on the beach and then treat yourself to a night at the historic Hotel Casa Del Mar and cap the night off with a meal at The Terrazza Lounge. You’ve earned it.

This article is sponsored by and is part of a series celebrating Boss Hunting’s favourite corners of the United States. Click here to see more, and thank you for supporting the brands that support Boss Hunting.

Boss Hunting



Share the article