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Route 66 is the quintessential American highway journey — a 2,500-mile odyssey throughout eight states from Chicago to Santa Monica.
And with 2026 being the route’s a hundredth birthday, this 12 months is the proper time to find what’s now a cultural icon.
Right here, we reveal the best way to do it effectively, with a information that steers you in the direction of an genuine Route 66 expertise.
We clarify how the highway acquired legendary standing, the diner in Chicago you must have breakfast at earlier than setting off and the risks of over-reliance on Google Maps for the journey.
Route 66 isn’t a race, and within the following part, we break down how a lot time to permit for the journey.
From there, it’s the not-to-be-missed sights that assist make the journey so splendidly eccentric, and among the finest motels to e-book into for a “good previous days” vibe.
The end comes at Santa Monica Pier, the place there are a handful of rituals to undertake to mark the top of a highway journey of a lifetime.
Route 66 highway journey information
The beginning of a legend
Route 66 was commissioned in 1926 and by the point it was completed and totally paved within the late Thirties, it stretched 2,448 miles throughout Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, from Chicago to Santa Monica — and it shortly attained legendary standing, regardless of not even being the primary long-distance freeway, or the busiest.
The route’s journey to cultural icon started with a whole lot of 1000’s of farmers from Oklahoma, Texas, Arkansas and Missouri utilizing it to succeed in California looking for work, a plight immortalized within the nice John Steinbeck’s highly effective 1939 novel The Grapes of Wrath, during which he dubs Route 66 the “Mom Highway.”
When automobile possession exploded after the Second World Struggle, Individuals found en masse that this highway of alternative was additionally a journey of journey that took them by bewitching desert landscapes and previous neon-lit motels and diners that may come to represent traditional highway journey tradition.
By the point the highway was decommissioned in 1985 and changed by the Interstate Freeway System, it was ingrained in standard tradition, that includes in songs comparable to Bobby Troup’s (Get Your Kicks on) Route 66, recorded by artists from Nat King Cole to the Rolling Stones, and making appearances in numerous highway journey motion pictures.
Sarcastically, its dying made it much more well-known, with preservation actions rising to keep up and restore motels, diners and roadside points of interest that have been now bypassed — as we speak Route 66 is a patchwork of historic sections.
Learn extra: How a lot of Route 66 stays after a century?
Begin in Chicago — the normal starting
Chicago is the normal launchpad — it’s the historic gateway to the west, and also you’ll principally have the solar behind you — and the ceremonial place to begin is amid the skyscrapers of the Windy Metropolis’s downtown district, on Adams Road, close to the Artwork Institute of Chicago.
There, you’ll discover a modest brown-and-white “Start Route 66” signal. Nevertheless, earlier than you drive previous it, custom dictates that you just head to close by Lou Mitchell’s restaurant and bakery on W. Jackson Boulevard, which has been serving breakfast to westbound road-trippers since 1923.
The menu is traditional diner fare, from espresso and pancakes to omelets and corned beef hash. And whilst you look forward to a desk, the serving employees hand out complimentary donut holes and Milk Duds.
When you set off, you’ll end up in one other world in little greater than an hour.
Excellent place to remain: Silversmith Resort Chicago Downtown is only a three minute stroll from the Route 66 and options rooms with mini-refrigerators, espresso makers and wifi.
Learn extra: Why your subsequent metropolis break needs to be to Chicago
Route planning (watch out for Google Maps)
Navigation-wise, it might be tempting to kind “Route 66” into Google Maps and take it from there.
However that may be a serious mistake. It’s value laboring the purpose that Route 66 is now not one lengthy steady freeway, however a mishmash of surviving segments jammed in amongst newer highways. Some authentic sections are fairly lengthy and scenic, others final for just some miles earlier than disappearing (and generally making a comeback a bit additional alongside).
Ask Google Maps for the route and also you’ll doubtless find yourself driving alongside interstates 40, 44 and 55, which changed giant sections of Route 66, and miss among the most fascinating roadside points of interest.
The secret’s to comply with the “Historic Route 66” indicators, which is able to lead you to among the most compelling sights and surroundings.
Learn extra: 5 under-the-radar highway journeys that get to the center of America
How lengthy you must enable for Route 66
Excellent: 14 days
At the moment, Route 66 isn’t a way to an financial finish — it’s the primary attraction, and driving at your leisure will imply you possibly can totally savor its delights. The Goldilocks timeframe? Two weeks, or 150-200 miles a day, when you’re dedicated to all the Route 66 Chicago-Santa Monica pilgrimage.
An extended journey means ample time to discover roadside points of interest, get pleasure from classic motels, and have an additional spherical of pancakes at a traditional diner.
Honest: 10 days
Ten days is a comparatively standard timeframe, that means a tempo of round 240 miles a day.
Nevertheless, some sightseeing will should be sacrificed. One technique could possibly be to select up the tempo within the jap part, then decelerate and 0 in on the extra dramatic surroundings provided by New Mexico, Arizona and California within the west.
Doable, however rushed: Seven days
A seven-day journey would imply a slow-fast-slow method, with sections of interstate used to hyperlink probably the most compelling sights. Stops would should be picked pretty rigorously upfront.
Keep away from: 4 days or much less
Shrinking the journey time to 4 days or much less would cut back the drive to a grueling interstate freeway marathon. If merely reaching the end line is the target, then be aware that the drive time is about 40 hours.
Learn extra: I drove within the US for the primary time – right here’s what shocked me on the 4,000-mile journey
Not-to-be-missed sights
Route 66’s irresistibly eccentric roadside tradition doesn’t take lengthy to emerge after leaving Chicago.
Round 90 minutes away is the city of Wilmington, house to the Gemini Large, a 30-foot fiberglass astronaut holding a rocket, a variation of the “Muffler Man” figures used to promote roadside companies throughout America.
Within the small city of Dwight, round 75 miles from Chicago is the fantastically preserved house-and-canopy-style Ambler’s Texaco Fuel Station, which dates again to the Thirties.
Cadillac Ranch, simply west of Amarillo in Texas, is obligatory. Created in 1974 by the artwork group Ant Farm, it options 10 traditional Cadillacs buried nose-first within the floor on the similar angle because the Nice Pyramid of Giza. They’re coated in graffiti, and guests are inspired to depart their very own spray-painted mark.
In Oklahoma, there’s the cheerful Blue Whale of Catoosa, an 80-foot-long vibrant blue concrete cetacean with a successful smile; and in Arizona you possibly can pull up within the ghost city of Oatman, the place burros wander the streets and “gunmen” stage Wild West shootouts.
Learn extra: Journey trip actions in America to check your health (and bravado)
Keep in a motel, not a series
Skip the chains and e-book into unbiased motels to be rewarded with a way more genuine Route 66 expertise. Household run motels sprung up in enormous numbers throughout the highway journey growth of the Forties and Fifties and there are nonetheless a number of fantastically preserved examples you possibly can keep in for a style of the “good previous days.” Listed below are three of probably the most celebrated choices:
Blue Swallow Motel, Tucumcari, New Mexico
The Blue Swallow Motel has been giving Mom Highway vacationers a cushty place to relaxation since 1939, and its yesteryear charms have been fantastically preserved: the neon signal promoting “100% refrigerated air” nonetheless glows above it and the rooms include Forties-era rotary dial telephones and classic lamps. Rooms from $120.
Wigwam Motel, Holbrook, Arizona
Friends have been staying within the Wigwam Motel’s distinctive concrete teepees for the reason that Fifties — and whereas the 15 models embody mod cons comparable to wifi and satellite tv for pc TV, the unique handmade hickory furnishings has been retained. Rooms from $105.
Boots Courtroom Motel, Carthage, Missouri
When Boots Courtroom Motel opened in 1939, company paid $2.50 to remain in one in all eight rooms accomplished within the “streamline moderne” architectural model. Every room got here with a carport and the property proudly marketed a “radio in each room.” At the moment, there are 13 renovated rooms for Route 66-ers to remain in and a guests heart housed within the former gasoline station. Rooms from $79.
Learn extra: Six epic rides coming to US theme parks in 2026 — together with the fastest-ever dive coaster
End on the Santa Monica Pier
Eight states and almost 2,500 miles of tarmac later, you’ll arrive at Santa Monica Pier the place you’ll discover a signal that merely says “Finish of the Path.”
It’s not probably the most celebratory piece of signage, however the exuberant environment, from road performers to the pier’s amusement park, make the event a fittingly jubilant one.
A well-liked ritual amongst highway trippers is to take a selfie on the signal, then stroll to the top of the pier and look again, inland, on the land mass that’s been tamed, earlier than a dip of the toes within the Pacific Ocean.
Excellent place to remain: The Shore Resort (rooms from $235) is instantly throughout the highway from the pier and provides rooms with balconies overlooking the seashore.
Good to know: Parking across the pier is congested, and whereas there’s a parking deck beneath the pier, it’s really useful to depart your automobile on the resort and stroll to the end line.
Learn extra: A sober information to Napa Valley
