Route 66 Road Trip and the American Southwest

May 23, 2012 by

North America, Places to Go, Suggested Itineraries, Things to Do

Road Tripping

Road Tripping

Road tripping is a form of travel that has been romanticized by generation after generation. There’s nothing that says “freedom” quite like the rumble of an engine and the open road.

And, when it comes to epic road trips, the United States might just be one of the best countries in the world to hit the road in. Not only is travel by car extremely easy here, but America is also so vast and varied that you can see a lot between Point A and Point B without even trying.

Road trip routes abound in the U.S., but one of the most popular has to be a Route 66 road trip. This stretch of road (now just a historic byway) has been memorialized in everything from songs to TV shows – it doesn’t get much more “American” than Route 66; Main Street of America; the Mother Road.

So, even though the Interstate system made the original Route 66 essentially obsolete (with I-40 largely replacing it), those road trippers looking for a taste of the historic highway can still get it by following the path of the former road. Even though it’s been replaced in many areas by newer, updated highways, the attractions that made Route 66 so popular are mostly still there.

Here, then, is a suggested summer road trip itinerary through the American Southwest that features Historic Route 66.

Chicago, Illinois

Cloud Gate Sculpture in Millenium Park

Cloud Gate Sculpture (also known as “The Bean”) in Millenium Park

Route 66 originally began up in Chicago, and therefore that’s where our journey begins. The Windy City is a great place to spend a few days exploring, with plenty to keep you busy. There’s a reason why some locals refer to Chicago as “the Little Apple.”

Before hitting the road, consider getting a taste of what Chicago has to offer: stand on the glass ledge at the top of the Willis Tower, visit “The Bean” in Millennium Park, devour some deep dish pizza, take an architecture boat cruise on the Chicago River, watch a baseball game at Wrigley Field, ride the Ferris wheel at Navy Pier, or catch an improv comedy show downtown.

After a day or two in Chicago, turn yourself toward the open road and the beginning of your American road trip.


St. Louis Arch

Gateway Arch in St. Louis

From Chicago, Route 66 traversed south through the state of Illinois, passing through cities like Bloomington and Springfield on the way to Missouri.

St. Louis – Missouri’s state capital makes a great first stop after Chicago, and is worth spending at least 2 nights in. Grab a burger at landmark Loop restaurant Blueberry Hill, check out the imaginative City Museum, and be sure to visit the Gateway Arch within the Jefferson National Expansion Memorial. At 630 feet tall, the blue-tinted arch is the tallest man-made monument in the United States. For $10, you can ride in a pod-like tram to the top of the Arch, where you can look out over downtown St. Louis and the slow-moving Mississippi River.

Meramec Caverns

Meramec Caverns

Meramec Caverns – Located a little over an hour from St. Louis in Stanton, Missouri, this cave system is now considered one of the primary attractions along former Route 66. There are billboards for miles advertising the Meramec Caverns, and they really do live up to the hype. Take a break from the Missouri heat and head underground for a guided tour through stalagmites, stalactites, and rock formations that are tens of thousands of years old. Admission is $19.50 for adults.


Oklahoma City

Oklahoma City

Oklahoma certainly is “where the wind comes sweepin’ down the plain,” as evidenced by the multitude of windmills that line the flat highways here. Many would suggest to just skip through Oklahoma altogether, but there are a couple of stops worth making:

The Blue Whale of Catoosa – If it’s quirky roadside attractions you’re after on this road trip, then you can’t skip the Blue Whale, located in Catoosa, Oklahoma. Chances are, if you’ve seen photos of the “top” Route 66 roadside attractions, you’ve seen photos of this famous whale.

Oklahoma City – As far as state capitals go, Oklahoma City is pretty standard. But it has a unique and moving National Monument that is worth visiting: the Oklahoma City National Memorial & Museum, which honors those lost in the 1995 bombing of the Alfred P. Murrah Federal Building. The outdoor Memorial is serene and thought-provoking, while the Museum is one of the very best you will visit. Admission is $12 for adults, and you should allow 3-4 hours to fully experience the site and museum.


Cadillac Ranch in Amarillo

Cadillac Ranch in Amarillo

From Oklahoma, it’s on to Texas – the Panhandle of Texas, to be exact. Historic Route 66 does not delve very far into the Longhorn state, but that doesn’t mean there aren’t stops worth making here. In fact, two of the most iconic Route 66 attractions can be found in this small slice of Texas.

Amarillo – Whatever you do, do not miss out on Amarillo. This city, located about halfway between the Oklahoma and New Mexico borders, is so full of Route 66 kitsch that you definitely want to stay overnight here and give yourself plenty of time to soak it all in. The two main attractions here include the Cadillac Ranch (a kooky art installation that consists of 10 Cadillacs buried nose-down in the desert, which you are encouraged to spray-paint) and the Big Texan (a steakhouse with a 72-ounce steak challenge and a ton of character).

Palo Duro Canyon – If you feel like making a detour off Route 66, consider a quick trip down to Palo Duro Canyon, not far from Amarillo. You may have never heard of it, but it’s actually the second-largest canyon in America, and is often referred to as “The Grand Canyon of Texas” both for its size (120 miles long) and its geological features, which are similar to those of the Grand Canyon.

*And now here is where we deviate somewhat from Route 66 for a while to take in some of the amazing sights of the American Southwest.

New Mexico

Pecos National Historic Park

Pecos National Historic Park

Don’t let anyone tell you that New Mexico isn’t worth visiting on your American road trip – if they do, tell them they are wrong (that and it’s impossible to drive the length of Historic Route 66 and skip New Mexico…)

Santa Fe – Route 66 technically ran through Albuquerque, but if you’re in search of a less-urban alternative to the state’s largest city, veer off and head for Santa Fe instead. Santa Fe is the capital of New Mexico, but don’t expect it to feel like any other state capital you’ve ever visited. This is a city of art galleries and farmer’s markets; of Spanish-style buildings and a slower pace of life. Pick a kitschy motel for the night (like the Silver Saddle), and spend the next day wandering around the little city of 70,000.

Pecos National Historic Park – About 25 miles outside of Santa Fe in the Sangre de Cristo Mountains, you’ll find Pecos National Historic Park, a former settlement site of local pueblo Indians. Walk through rust-colored ruins and marvel at the beautiful scenery of northern New Mexico. With an admission charge of only $3, this is definitely a stop worth making.

Four Corners Monument – As you make your way westward, consider another detour north to the Four Corners Monument – the spot where the corners of New Mexico, Arizona, Utah, and Colorado meet. This is the only spot in the United States where 4 states meet, and makes a fun stop. The Four Corners region is also chock-full of beautiful places to visit (more on some of these later).


Monument Valley

Monument Valley

After winding through the colorful buttes and big skies of northern New Mexico, Arizona should be your next stop – or, should I say, series of stops. If it’s amazing, natural beauty you’re searching for, you can find plenty of it here in northern Arizona. While not all of these suggestions are exactly along Route 66, that shouldn’t stop you from making a long detour.

Page – This town near the Utah border is an ideal location to base yourself for a few adventure-filled days. The town is small and touristy (definitely book accommodations well in advance), but so close to so many things that its proximity makes up for its price tag. Page’s claim to fame is Antelope Canyon – the Upper portion of the canyon is famous for its narrow slot canyon walls and dazzling midday light beams – and the town is also close to Lake Powell and Glen Canyon National Recreation Area. If a hotel in Page doesn’t sound appealing, consider renting a houseboat on the lake.

Monument Valley – Roughly two hours from Page on the Arizona/Utah border, Monument Valley lies in an area that probably would be a national park if it weren’t located on Navajo lands. Consider a day trip to Monument Valley from Page. Take a hot air balloon ride over the buttes and mesas, sign up for a back-country tour of arches and famous movie sites, or simply drive the 17-mile road through the park.

Grand Canyon North Rim

Grand Canyon North Rim

Grand Canyon North Rim – Also about 2 hours from Page, the North Rim of the Grand Canyon must appear on your list. Only about 10% of all visitors to the Grand Canyon visit the North Rim, which means it’s usually much quieter and less crowded – but no less breathtaking.

Grand Canyon South Rim – Once you decide it’s time to return to Route 66, consider doing so by driving around the Grand Canyon, adding in a stop on the South Rim. While much more “touristy” than the North Rim, the South Rim is still stunning and has many more viewpoints.

Sedona, Arizona

Sedona, Arizona

Sedona – If you’d like an alternative to Flagstaff (which is actually along old Route 66) head half an hour south to Sedona for a night or two. Explore Red Rocks country in style, slip down a natural water slide at Slide Rock State Park, and visit one of the area’s mystical vortexes.

*If you decide you want to stick to a true Route 66 route, skip everything listed here after Santa Fe and substitute Albuquerque and Petrified Forest National Park in Arizona before heading to Sedona/Flagstaff.


Las Vegas, Nevada

Las Vegas, Nevada

Unfortunately, Nevada does not fall along old Route 66 either. A true route would go straight into California from Arizona… but where’s the fun in that?

Las Vegas – No American road trip would be complete without at least a night or two in Sin City itself – Las Vegas. Located less than 5 hours from Sedona, Vegas can (and should) be a fun addition to your trip. You can usually score great deals on hotel rooms too – perfect for road trippers on a budget. And on the way to Las Vegas, be sure to make a stop at the impressive Hoover Dam.


Santa Monica, End of the Trail

Santa Monica, End of the Trail

The last state your journey will take you through is California. Taking the historic route through the state will see you passing through ghost towns, the Mojave Desert, and more. Be sure to stop off in Barstow to visit Elmer Long’s Bottle Tree Ranch – a “folk art forest” in the desert – and spend a night at the Wigwam Motel in San Bernadino. (If you’re coming from Las Vegas, you will likely still come through Mojave and will catch back up with Route 66 near Barstow.)

And last, but not least, you’ll have to visit Venice Beach and the Santa Monica Pier – the End of the Road when it comes to Route 66.

This one-way route could be done in about 2 weeks, but definitely allow more time if you’re prone to exploring and impulsive stops at roadside attractions.

-Amanda Williams

All photos provided by Amanda Williams.

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One Response to “Route 66 Road Trip and the American Southwest”

  1. Jennifer Says:

    It sounds like a road trip down Route 66 is the best way to visit all of the top cities in the U.S.