Thanks to Nat King Cole, it’s the most famous road in the United States, spanning 2,451 miles from Chicago to Santa Monica and serving as the backdrop for that All American road trip you and your pals have been meaning to go on. Yes, y’all, we’re talking about the “Mother Road” of the red, white, and blue—also known as “The Will Rogers Highway.” With broad and curvy roads meandering through popular cities from St. Louis and Albuquerque to Amarillo and L to the A, Route 66 truly captures the essence of Americana at its best. It may no longer be a part of the U.S. highway system, but that doesn’t make it any less of “America’s Main Street.” Even a century later, the scenic wonder continues to capture the hopeful hearts and souls of road trippers driving westward in search of the American Dream.

It really is a storied path to say the least—a phenomenally iconic stretch of dirt road that’s perfect for those wanting to snooze, cruise, and absorb a broad cultural cross-section of our mighty fine country. So buckle up those kids in the back of that SUV or maybe strap on a helmet and some boots while revving up your shiny new Harley. There’s a lengthy list of unique attractions all along this magnificent motor way. Drive safe and have yourself a quirky (and kind of kitschy!) but truly quintessential American road trip to remember. Here are fourteen must see places to explore along Route 66.

Plan the Ultimate Route 66 Road Trip

1. Chicago, Illinois

Sitting smack dab on Lake Michigan, this quintessentially American city serves as the

starting point of “The Main Street of America.” Yes, that’s right, the open roads of Route 66 officially start at the edge of Grant Park (a.k.a. “Chicago’s front yard”), a large and centrally located urban wonderland that’s been host to the 1893 World’s Fair, as well as the honored site of Lollapalooza and Barack Obama’s 2008 election acceptance speech.

Make sure to begin that grand tour of the infamous Route by fueling up at Lou Mitchell’s, a more than popular eatery founded in 1923 that sits next to Chicago’s Union Station. It’s been hailed as "the First Stop on the Mother Road,” has long been a destination for presidents and prominent politicians on the campaign trail, and is the only spot in America that doles out millions of fresh donut holes and complimentary Milk Duds to customers waiting in line. This iconic Chicago fave is the perfect spot for hungry drivers to load up with energy before hitting the open road. So after gobbling up some classic dishes such as meltaway pancakes, a skirt steak sandwich, and some of "the world's finest coffee,” head on over to the entrance of Grant Park to start that long awaited journey. Don’t forget to sneak a peek at that “End Historic Route 66” sign at the intersection of Jackson Boulevard and Michigan Avenue!

2. Northern Arizona

It’s safe to say that most of Route 66’s allure doesn’t always come from its infinite amount of 1950s and 60s American kitsch. Instead, it comes from the gorgeous nearby Western United States landscape that you’ll be passing through, especially in Northern Arizona, one of the most beautiful parts of the open road. You’ll cruise past memorable destinations such as the stunning Painted Desert, the 225 million-year-old Petrified Forest, the iconic Grand Canyon, as well as the the thirty-seven-mile-wide Meteor Crater. All these spectacular sites are picture perfect and postcard worthy indeed—the ultimate spots to take in all that Mother Nature has to offer.

3. Santa Fe, New Mexico

Nestled in the foothills of the Rocky Mountains, the capital city of New Mexico is no doubt the “Land of Enchantment.” It’s a magical land filled with breathtaking natural beauty, Native American culture, and a whole bunch of folk festivals, delicious Southwestern food, friendly locals, and world renowned art galleries—such as the Georgia O’Keeffe Museum, which houses more than 3,000 works of art and more than 1,000 paintings by its namesake. It opened up shop in 1997, just eleven years after the artists’ death, and is also the site of the Georgia O’Keeffe Museum Research Center, which is dedicated to advancing the study and knowledge of American Modernist Art.

Go buy a pair of hard-to-find Native American turquoise earrings, have a drink in the Dragon Room at the Pink Adobe, and catch some live music at Santa Fe Plaza at this Pueblo-style hotspot offering crooked roads, adobe landmarks, and powdery white winter snows from the Sangre de Cristo Mountains. What are you waiting for?

4. Gallup, New Mexico

While you’re at it, why not road trip on over to another New Mexico favorite in McKinley County—the populous city of Gallup?! It sits right in between Flagstaff and Albuquerque along the historic road, and because of all the rugged terrain nearby, was a popular filming location for 1940s-50s Hollywood Westerns.

To get even more star struck, mosey over to El Rancho Hotel, a classic abode that’s played host to Hollywood stars from John Wayne to Clint Eastwood. The landmark hotel is listed on the National Register of Historic Places and has even been fully preserved to retain its classic Southwestern charm—it’s got simply decorated Western-style furnishings featuring wagon-wheel headboards as well as an entire room named for the late Ronald Reagan. Giddy on up!

5. Tucumcari, New Mexico

If you just so happen to be craving even more New Mexico, follow the iconic "Tucumcari Tonite" signs along the open road to get the feel of a seriously way-out-there vibe. With curio shops and dazzling diners dating back to the glory days of Route 66, this Quad County city is one of the highway’s most well-preserved towns—a favorite overnight stopping point for all road trippers.

Start off at the historic coral-and-sky-blue Blue Swallow Motel, a twelve-unit space with a cozy courtyard that’s great for taking in massive orange sunsets. It’s the best spot in town to sit, talk, wine, dine, and listen to the neon buzz with your closest pals before sneaking in some Zzzzz’s (Another fluorescent-light-laced motel to that tops the list would be Motel Safari). And for the ultimate date night with your sweetie-pie, head over to the just renovated Odeon Theatre on South 2nd Street. According to owner Robert Lopez, a cotton farmer, "It's the only place you can go” for Friday night fun!

6. St. Louis, Missouri - Chain of Rocks Bridge, Meramec Caverns

Spanning the Mississippi River, this major Missouri port and city is literally the “Gateway to the West.” On the north end, there’s the infamous Chain of Rocks Bridge which features a prominent twenty-four-degree turn at its midsection (which was necessary for boats navigating the river). This Route 66 landmark opened in 1929, but was closed for repairs in 1968 and has never been reopened to automobile traffic since. Fortunately, the span was renovated for pedestrian and bike use in 1998. Seriously, before making the drive across the Mississippi into Missouri, you’ve got to walk down this riverfront trail — those beautiful castle-like water intake towers down the stream will have you in awe for sure.

What’s more is that at the Illinois-Missouri border, there’s also the 400 million-year-old Meramec Caverns, a destination that attracts more than 150,000 Route 66 trip visitors on a yearly basis. Another spot is The Delmar Loop located just off the road--- it’s transformed in the past four decades from a drug den to an entertainment district with an eye for the past. The go-to hub is probably Blueberry Hill, a buzzing, pub-style restaurant and music club featuring vintage jukeboxes, original Beatles dolls, and some of the best local burgers.

7. Amarillo, Texas

It’s not every day that you see a bunch of old Cadillac automobiles buried nose-down into the dirt road in a tidy little line facing West. But in Texas’ fourteenth most populous city, it’s actually a normal everyday site, a true ode to the quirky and weird Americana kitsch that’s often found on Route 66.

Known as Cadillac Ranch, this Amarillo hotspot has welcomed fans of public art, cars, and the infamous Route 66 since its creation in 1974 by a group of artists known as The Ant Farm. Over the years, countless individuals have released their inner artist by using the junker cars as a graffiti canvas. Go spray paint to your heart’s content at this Mother Road beauty-- it really is the ultimate art-infused roadside “carscape.”

8. Claremore, Oklahoma

Who doesn’t love themselves some Will Rogers? The infamous newspaper columnist, cowboy, vaudeville performer, humorist, social commentator, motion picture actor, political pundit, radio legend, and philosopher is no doubt one of America’s most beloved personalities—he also happened to be a native Okie, hailing from none other than the town of Claremore.

Hence, the state of Oklahoma named the entire northeastern region after the late entertainer (a.k.a. Rogers County). Route 66 shows even more adoration for the guy by having built a museum in his honor at the Will Rogers Memorial Museum. So take a break from all that car-sitting and go explore fine collections of art, artifacts, and memorabilia that bring back to life "Oklahoma's Favorite Son."

9. Chelsea, Oklahoma

Speaking of Rogers County and the great Mister Rogers, here’s another cannot miss place just about three miles off of Route 66. Ed Galloway’s Totem Pole Park, which holds the record for the world’s largest concrete totem pole, spans over fourteen acres and is the oldest and largest example of a folk art environment in Oklahoma. The site consists of eleven objects and one building that’s merely ten miles north-east of Claremore. Plus, while cruising along Route 66 to the park, you can also see some other iconic sights such as the Blue Whale or the Route 66 Museum. The latter is operated by the Oklahoma Historical Society and is the best space entirely devoted to the fabled highway, featuring retro exhibits, vintage cars, as well as an indoor “drive-in theatre” where you can see how the route became an indelible part of American history.

What’s more is that there are quite a handful of 66-era motels and diners all along Oklahoma Route 66—you can even grab some tasty beef jerky from the oversized shack at Jiggs Smokehouse in Clinton. There’s no better place to experience true American mobility and the freedom of the wild road!

10. Oklahoma City, Oklahoma

Even more Oklahoma and classic Route 66 kitsch can be found at the state’s capital, a city that’s full of cowboy culture, working oil wells, world-class shopping and dining, as well as a giant milk bottle crowning a tiny, triangular former grocery store that’s not known as Saigon Baguette. Yes, the site of The Milk Bottle Grocery is definitely one of those icons you just have to see for yourself. Plus, if the sight of all that milk leaves your tummy grumbling, you can always stop in for some pho and boba milk tea at the Vietnamese sandwich shop that now stands in all its glory.

11. Amboy, California

Who would’ve ever guessed that there are seventy-six shoe trees in America? Sure, it’s a weird quirk, but it’s also a nice little tradition that’s worth preserving-- which is why you’ll find yourself face to face with the famous Route 66 Shoe Tree in Amboy, an unincorporated community in California’s Mojave Desert.

There’s also Roy’s Motel and Café, a now-defunct Route 66 landmark that’s owned by a preservationist named Albert Okura who plans to reopen it. It's well-known for its “Googie” architecture, a type of futuristic style from the 1950s that can be most famously seen in the “Welcome to Fabulous Las Vegas” sign in Nevada.

12. Amboy, California

Not too far from the Grand Canyon on Route 66, you’ll find one of three remaining Wigwam Motels on the Mother Road (the others are in Rialto, California and in Kentucky). From the seven original Wigwam Villages, there’s a spot in Holbrook where you can stay in teepees made of concrete and steel, as well as brag that you’ve dared to dangerously-- no one really has to know that all the tall and cone-shaped rooms in the hotel chain actually contain all of the amenities of any regular motel (i.e. bathrooms, carpeting, and air conditioning)! Plus, for animated movie fans, the motels were a Route 66 inspiration for the movie “Cars,” in which characters sleep in giant traffic cones at the Cozy Cone Motel.

So get yourself a nice helping of original handmade hickory furniture, classic cars, and kooky Route 66 memorabilia dating all the way to the 1930s—and don’t you dare ignore that infamous "Do it in a teepee" sign as you continue trekking west. What’s better than sleeping in a well kept-up teepee that faces a palm-dotted lawn with a pool? Nothing, really.

13. Amboy, California

Kansas may have the shortest section of the legendary highway at only thirteen miles in all, but there’s a nostalgic little sandwich and gift shop housed in a restored service station on the road that lets you step back in time to enjoy a classic slice of Americana—and some good old apple pie.

Four Women On The Route features all the amenities that would have been seen along the route half a century ago, and even displays a 1951 mining boom truck right outside that inspired the character “Tow Mater” in the 2006 animated movie Cars.

14. Santa Monica, California

There couldn’t be a better way to end that road trip than by heading on over to the Santa Monica Pier, a classic American boardwalk along the mighty Pacific Ocean that’s filled with local beach bums and flocks of international tourists all coming together to unwind and enjoy everything from arcade games, historic carousels and hippodromes, a trapeze school, and a light-up Ferris wheel, to street performers, endless cotton candy, and some truly dazzling summertime fireworks.

The sunny SoCal landmark opened up in 1909 and was officially designated as the “western terminus” of Route 66 in 2009— it even features a big old sign declaring that you’ve reached the “End of the Trail.” It’s the perfect way for road-weary travelers to refresh and rejuvenate after a long trek across the states. So finish off that journey with some gorgeous sights of sand, surf, sun, and sea—the amazing beauty and energy of Cali will warm your heart, mind, and soul.

This article was written by Pamela Chan.