Road tripping Route 66

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Completed in 1938, legendary Route 66, which once served as the primary course between Chicago and Los Angeles, serves today as a place to experience the freedom of the open road and many of America’s iconic sights. It’s over 2,200 miles long and features countless attractions, ranging from classic diners to somewhat strange places that you can only experience in the U.S., like Cadillac Ranch, basically just a bunch of old junker Cadillacs planted in the ground, and all sorts of kitschy roadside museums.

Route 66 is no longer part of the U.S. highway system, and many of its sections have fallen into a state of disrepair, or are dirt roads. In fact, parts that haven’t been absorbed into other roadways can’t even be found on a map anymore. That said, there are still plenty of major portions of the route that are still there, allowing you to experience its highlights. Want to check Route 66 out for yourself? We offer a fantastic 15-night self-drive of Route 66, or if you prefer escorted tours we have a great 14-night Chicago to Golden Gate tour that includes the Route 66 landmarks.

So, are you ready for an iconic road trip?

Chicago

The journey begins in Chicago and travels through St. Louis, Oklahoma City, Amarillo, Santa Fe, Albuquerque and Las Vegas, before culminating in Santa Monica on the California coast.

Spend some time exploring the Windy City before taking off on your adventure. Chicago has something for everyone, from food and shopping enthusiasts to theatre and museum lovers, and more. The possibilities are practically endless. Head to the Magnificent Mile to do some shopping for your trip, or visit Grant Park, home to one of America’s top museums. The one-million-square-foot Art Institute of Chicago displays one of the finest collections of Impressionist paintings on Earth, along with remarkable works from the likes of masters Picasso, Dali and Warhol.

One must-do here is The Ledge Experience, which has transformed the way visitors view the city. An unmatched view of Chicago is enjoyed while standing on The Ledge from 103 floors over Wacker Drive and the Chicago River. If that heart-pounding experience woke up your appetite, dine at the Angry Crab, which offers family-style Cajun-spiced seafood and an experience that’s been called one of the “most fun and messiest eating experiences in town.” You’ll eat at communal tables that are set among fish, anchors, netting and walls signed by previous customers.

In the morning, there is one last thing to do before you go, fuel up with breakfast at Lou Mitchell’s in the heart of The Loop, a Chicago institution since 1923, renowned for providing a delicious send off to travellers that are headed out on historic Route 66.

On the road in Illinois

Your first stop is in Wilmington to see the Gemini Giant, a space age Muffler Man, named after the Gemini space program. If you’re into the quirky, and perhaps the downright weird, this 30-foot-tall statue holds a silver rocket while wearing a space helmet and looks a bit like a creepy serial killer, particularly because of the look on his face. Take a selfie with him and show it off to all your friends so they can get a glimpse of you taking in some of America’s most truly bizarre.

Make time for at least a quick visit to one of America’s most charming towns, Pontiac, home to the Route 66 Association Hall of Fame & Museum, home to thousands of historic memorabilia items from the glory days of the road. Hearing the tales about life here during the time it was at its peak, and learning about its history, will set you up for an even more rewarding experience, and you can capture of photo of your car in front of the largest Route 66 shield mural too.

St. Louis

If you need to get out and stretch your legs, this old Route 66 town is a great place to do just that. St. Louis is home to the Gateway Arch, an iconic symbol of the city that marks the spot Lewis and Clark set out on their historic expedition. Take one of the eight lifts that run 630 feet up to the observation deck sitting at the highest point of the arch, for a spectacular bird’s-eye view. At the Victorian-era Missouri Botanic Garden. the oldest botanical garden in the U.S. and a National Historical Landmark, stroll through 79 acres, viewing a wide array of plants, trees and shrubs, including an astounding collection of rare orchids.

The Chain of Rocks Bridge is yet another great spot for a walk. It spans the Mississippi, from Illinois to Missouri, but what makes it unique is that it has a dramatic 22-degree bend halfway across the river. While Route 66 drivers once crossed it, today it’s open to foot and bicycle traffic only, in addition to offering a fabulous view of the famous Arch.

Before reaching Oklahoma, pay a visit to Meramec Caverns, a popular tourist attraction for more than 80 years, and possibly the oldest stop on the route. Take a guided tour to see this seven-level natural underground wonder and pick up a treat at the candy store.

Oklahoma

Oklahoma boasts more driveable miles along the Route 66 than any other state, and it even offers the chance to see a whale. Admittedly, this one is more than a little out of place, but when you’re driving along and reach a pair of side-by-side bridges in Catoosa, that’s just what you’ll see. The smiling, blue beached whale was an odd anniversary gift from a man to his wife. The 80-foot-long creature rests in a pond that was once part of a park that featured an animal reptile kingdom. While the park shut down in 1988, the toothy whale makes for another must-stop, as well as a good place for a picnic.

In Clinton, another Route 66 museum awaits, this one chronicling the part of the Mother Road that bisects Oklahoma. Check out the neon sign and the cherry-red ’57 Chevy in the front window before stepping inside and walking the “Main Street of America,” to view displays that reveal tidbits about the places along the route that no longer exist.

Texas

As you enter Texas, be sure to save up a big appetite for what awaits this evening – a steak dinner at the Big Texan Steak Ranch in Amarillo, home to the whopping 72-ounce steak. Even better is that it’s free. There is a catch, you’ll have to down the whole thing in under an hour. Once you’re fed, rested and ready to get back on the road, just outside of Amarillo check out Cadillac Ranch. This public art installation created in 1974 features ten sets of perfectly aligned graffiti-covered tail fins that are buried at the same angle as the Great Pyramid, standing as a tribute to the American Dream. Not only is contributing your own graffiti legal, but it’s welcomed. Spray paint your initials, or your hometown like many others do, or come up with your own creative work.

New Mexico

When you reach Santa Fe, New Mexico, the oldest capital city in the nation and the stunning jewel of the Southwest, you’ll be about three-and-a-half hours past the midway point of the trip. This is a great place to take a break from being behind the wheel for a couple days or more, with lots to see and do. The city claims to host the oldest public building in the U.S., the Palace of Governors, built in 1610, and the oldest community celebration, the Santa Fe Fiesta, which started back in 1712. Start at The Plaza, browsing the handmade jewellry and impressive works of art, before wandering through the winding streets lined with adobe-style buildings that house boutiques, art galleries, historic sites and museums.

Sample some of the best of Santa Fe’s diverse and exciting food scene by joining a food tour. Starting in the heart of downtown, they offer the chance to try lots of delicious local specialties, including red and green chili peppers as well as a range of popular Southwestern dishes.

In Albuquerque, famous for its colourful hot-air balloon fiesta, discover a multitude of cultural attractions including film, arts, music, dance, literary, and craft organisations as well as museums and all sorts of other festivals, while the picturesque Sandia Mountains provide a welcome backdrop. Stick around long enough to take the world’s longest aerial tramway, the Sandia Peak Aerial Tramway which climbs 2.7 miles up the steep western face of the mountains. From the observation deck at the 10,378-foot summit, you’ll see Santa Fe to the northeast and Los Alamos to the northwest.

Plan to stop often for photo-ops along the section of roadway from Albuquerque to Gallup, one of the route’s most scenic sections. You’ll quickly find out just why this state is known as The Land of Enchantment.

Arizona

Just over the border into Arizona near the town of Holbrook, the Petrified Forest National Park is another must-experience, offering the opportunity to view one of the largest and most vibrantly-hued collections of petrified wood, along with archaeological sites and historic structures that are set among the striking natural beauty of the Painted Desert. The trees are actually ancient, 250-million-year-old fossilized logs, and many are gigantic, up to six feet in diameter, boasting an array of colours, in shades of blue, red, amber and purple, with at least one spanning a ravine to form a natural bridge. If you’re up for a hike, you’ll find a number of short treks, ranging from less than a half-mile to three miles, each promising an amazing view.

A short drive further west is the town made famous after being featured in the Eagles’ hit song “Take It Easy.” Its line “I’m standing on a corner in Winslow, Arizona,” made it a popular stop along the route, and it since built a park to memorialise it. The park offers the chance to stand on a corner in Winslow yourself, and also features a statue of a man with a guitar and a mural of scenes from the song.

One of the highlights of any Route 66 trip is Grand Canyon National Park, one of the Seven Wonders of the World, and one of America’s most popular attractions, thanks to its brilliant shades of colours and unforgettable panoramas. Something that must be seen in person to be believed, the canyon measures in at an average width of ten miles, a depth of one mile and length of 277 miles, but those numbers won’t really prepare you for that first impression that’s practically guaranteed to literally take your breath away. Don’t just experience one view point, walk around the rim to see it at all angles for a variety of stunning perspectives.

Try to tear yourself away from those vistas in time to reach downtown Williams by 7 p.m., when you can catch the nightly Old West shootout, featuring cowboys and the classic outlaws of the world famous Cataract Creek Gang.

Nevada

About 30 miles before reaching Las Vegas, AKA the “Entertainment Capital of the World,” pay a visit to Hoover Dam on the border of Nevada and Arizona. At the time of the dam’s completion in 1936, it was one of the largest manmade structures in the world, and a true marvel at the time. At 726-feet-tall and 1,244-feet-long, its vast size can only truly be appreciated by seeing it person.

Once in Sin City, you can enjoy the things it’s famous for, including trying your luck at gambling, or even swimming with sharks. But the one must-do is catching a show – whether you attend a Cirque du Soleil performance, see the Blue Man Group or something else, it’s sure to be a highlight of your driving tour.

California

The last leg of your journey brings you to Santa Monica. Celebrate the experience by taking a ride on the world’s only solar powered Ferris wheel on the Santa Monica Pier, a staple in the Los Angeles area for more than a century. Sink your toes in the sand at the beach, and when you’re ready to get back in your car again, you’ll be perfectly situated for visiting all of those famous sights, from the Hollywood Walk of Fame to the shops in Beverly Hills and Disneyland.