2 Week Route 66 Road Trip Itinerary

It’s America’s Main Street, the Mother Road. The legendary Route 66 has captured travelers’ imaginations for nearly a century and it’s topped my personal bucket list for years. My solo round-the-world trip left me very well traveled internationally, but I’d still seen so little of my own country! Add in an early dating conversation with my now husband where we dreamed up a Route 66 road trip covering the full span from Chicago to Los Angeles, there was no way I was honeymooning anywhere else. Consider this your battle-tested 2 week Route 66 road trip itinerary!

History of Route 66

Established in 1926 as part of the United States’ first major highway development, Route 66 originally stretched over 2,400 miles from Chicago, Illinois to Santa Monica, California. Over the course of the 20th century, it played pivotal roles in westward migration following the Dust Bowl, mobilization during World War II, and the postwar boom of tourism when cross country road trips became the ultimate dream for classic family vacations.

Driving Route 66 has never been about getting from point A to point B. All those cliches about the journey mattering more than the destination? The Mother Road rules at this! Even though the official highway was decommissioned in 1985 and largely replaced by bigger interstates, that spirit of wandering exploration among America’s small towns and diverse landscapes is still very much intact.

Some sections of the original Route 66 have been preserved and even when you do have to take slightly different driving directions, you can still piece together attractions and landmarks that celebrate the essence and nostalgic charm of Route 66.

When is the Best Time of Year to Road Trip Route 66?

My 2 week Route 66 road trip took place in late May and early June and this was a great time of year. Temperatures are warm, but there are relatively fewer mega hot days, and we beat schools being out of session so destinations were not crowded with vacationing families.

I would wager a guess though that the actual best time to visit Route 66 is in the fall. In October, you would get a little fall foliage in the Midwest and a chance to plan your trip around the International Balloon Fiesta in Albuquerque.

Do You Really Need 2 Full Weeks to Travel Route 66?

Yeah, you really, really do. While you could technically drive Route 66 in a shorter period, you would hardly have time for anything but driving. When I planned our itinerary, I wanted to ensure we wouldn’t have to hit the road any earlier than 10 am and that we wouldn’t need to spend more than about 6 hours driving in a single day. This gave us an easier pace to the trip and honestly… it still wasn’t enough!

I think the ideal length for a Route 66 road trip would be a month. There were still lots of stops we missed out on and, with only one exception, we never spent more than one night in a single city. An itinerary longer than 2 weeks would have allowed us to have full days in major cities like Chicago, Tulsa, and Los Angeles, as well as more time to explore small towns and “ooh I wonder what that is?” roadside attractions.

As is, a 2 week Route 66 road trip itinerary is just enough to experience the whole road from tip to tail and get an introduction to everything it has to offer.

How to Navigate While Traveling Route 66

Navigating Route 66 can be a bit of an adventure in itself, since a lot of the original highway has been replaced by the interstate system or simply fallen into disrepair after its decommission.

Important Note: Google Maps will almost always default you to interstate heavy directions. The point of Google Maps is to efficiently get you from point A to point B and we have already covered that this isn’t the spirit of a Route 66 road trip. This 2 week Route 66 itinerary relies on a balance of faster interstate travel and classic Route 66 driving.

I highly recommend getting a set of Ghost Town Press’ Route 66 maps. There is one for each state along the Mother Road and they’re illustrated by Route 66 legend Jerry McClanahan to be kind of like a treasure map. In addition to detailed written instructions on how to stick to the original Route 66 highways still in existence, there are these great illustrations of the road and its attractions. There are quite a few stops we made that didn’t come up in my advance research at all and we never would have known about them without these maps!

(Disclaimer: I am an Amazon affiliate, so I may earn a small commission from anyone that uses that link to make a purchase. All opinions are my own and I only link to products I actually use or consider trustworthy. These really are the exact maps I used to navigate Route 66.)

While you drive, there are also frequently brown signs for Historic Route 66 that can help you stay on track.

We also frequently hacked our Google Maps use by plugging in lots of specific towns and attractions for a multi-stop itinerary that made it easier to select the scenic route option.

I’m also going to throw out one final tip: sometimes the “original” road is a service road running directly parallel to the interstate. You could be driving the interstate and have the “real” Route 66 in your sights the entire time, or vice versa, so it’s often not a big difference and you might as well embrace the higher speed limit and smoother ride of the interstate. Those Ghost Town Press maps will help you visualize when the road is parallel and when you really do need to be on Route 66 proper.

What to Pack for a Route 66 Road Trip

I’ll share a complete packing list elsewhere, but here’s a quick overview of how to pack for a Route 66 road trip.

You’ll need clothes for varying climates. Your starting point in Chicago will be much cooler and nights in the desert could also get pretty chilly, while desert daytime temps could hit triple digits even in early June. Don’t forget a rain jacket!

Consider whether you’d like to have any fancier nights out, particularly in Chicago and LA and include reasonably dressy shoes.

This 2 week Route 66 itinerary does include some hiking, but you don’t necessarily need heavy duty hiking boots. I’m a big fan of trail runners or any sneaker with decent traction for day hikes.

This itinerary is also built around flying into Chicago, renting a car, and flying out of Los Angeles. I’m a huge proponent of carry-on only travel, but remember that you’ll have a rental car for the actual itinerary to help you spread out. You can stock up on items like toothpaste, sunscreen, and snacks on the road.

How Much to Spend on a Route 66 Road Trip

Like the packing list, I’ll have a more detailed budget breakdown available soon, but here are some essentials to plan for. Fair warning: between U.S. prices, more comfortable and private travel than my budget backpacking days, and paying for 2 people, my Route 66 road trip is the most expensive trip I have ever taken!

How much does a one-way car rental cost? One-way car rentals are typically more expensive than rentals where you are returning the vehicle to its original location. I spent a little under $100 per day for a mid-size SUV from Alamo, and offset about half of that ultimate cost using credit card points and miles. 

Obviously, you also need to budget for gas. Route 66 is a loooong road trip. We gassed up a total of 9 times, but those weren’t all full tank refills, some were top ups.

Motels are a classic standby for any Route 66 road trip and typically run about $100 to $150 per night. There were some hotels we spent more like $200 a night on and the final hotel in Santa Monica on this itinerary is a doozy at $500 a night… but we paid for this in full with credit card points and miles.

We typically spent $15 to $30 per person on meals, but there were some where we splurged more. We cut costs on dining by stocking up on breakfast items at grocery and convenience stores, so we weren’t going out for every single meal.

Definitely plan on getting an annual National Parks pass for $80. (If you’re a U.S. military veteran, you can get this pass for free!)

And of course you want some money for museums, parks, other attractions, souvenirs, etc.

In total, a two-week Route 66 road trip can cost anywhere from $3,000 to $5,000. Without a nice big cache of points and miles, this trip probably would not have been possible for me, and even with that help, there’s a reason I saved this trip for my honeymoon. It’s a true special occasion trip!

Full 2 Week Route 66 Road Trip Itinerary

Day 1: Arrive in Chicago

Your Route 66 adventure kicks off in Chicago. 

If you have an early flight arrival, you can fill your day with iconic Windy City attractions like the Cloud Gate (aka “The Bean”) in Millennium Park, the Art Institute of Chicago, or a deep dish pizza lunch. But I really recommend taking it easy and saving Chicago sightseeing for its own trip.

Save some time in your arrival day for hitting up a Walgreens or other convenience store and stocking up some necessary supplies.

In the evening, grab dinner at Navy Pier. Offshore Restaurant has some nice waterfront views.

Where to Stay in Chicago

The Palmer House is an amazing hotel to start your Route 66 journey. While today it is owned by Hilton, the hotel itself dates back to 1873 so it was well established by the time road trippers took to Route 66 in the 1920s and beyond. The lobby and restaurant/bar area are fabulously ornate and rooms are comfortable. You get such an amazing bang for your buck here too – it’s about $200 a night for a much nicer historic hotel than the average corporate cookie cutter spot.

Day 2: Small Towns of Illinois (Chicago to Springfield, IL)

Today we start driving Route 66 in earnest, crossing many of Illinois’ small towns and farmland.

Start your day with a hearty breakfast in Chicago. Lou Mitchell’s is a Route 66 icon, open since 1923. Unfortunately, during our trip it was closed for Memorial Day weekend, so I can recommend an alternative: the Pittsfield Cafe. The Pittsfield building opened in 1927, just one year after Route 66 was originally commissioned, and at the time it was the city’s tallest skyscraper. The Pittsfield Cafe inside dates to the 1980s, so it’s not quite as historic, but let’s not forget that the 80s were about 40 years ago – this cafe has its own little sense of diner time capsule.

When it’s time to start driving, there is a sign marking the official start of Route 66 right across the street from the Art Institute of Chicago. Go snap a selfie with the sign and the Sears Tower in the background.

Rialto Square Theater

Your first stop is Joliet, Illinois, about 1 hour from Chicago, home to the historic Rialto Square Theater. Take a moment to admire the beautiful architecture of this 1920s vaudeville movie palace, often referred to as one of the most beautiful theaters in the country.

Burma Shave Signs

By this point, you will be far enough outside Chicago to have less interstate driving and you can enjoy some of the scenic historic Route 66, complete with Burma Shave signs! Burma Shave was a shaving cream brand that had just been founded around the time Route 66 was built and they got famous for these silly roadside signs they set up along the highway. You’ll see little series of red signs detailing rhymes that often include a joke about driving safety. My favorite is: “Don’t stick your elbow out too far. It might go home in another car!”

Muffler Men

One of the most popular Illinois attractions on Route 66 is the Gemini Giant, one of many Muffler Men statues along the highway. As of May 2024, the Gemini Giant had been taken down for restoration and will be moved to a new location within Wilmington, Illinois. You will have a chance to see other Muffler Men statues later in your trip!

Gas Stations

Route 66 is peppered with old gas stations, many of which have been restored and turned into photo ops or small museums packed with Americana kitsch. One of the best ones is in Dwight, Illinois: Ambler’s Texaco Gas Station. This place felt like walking into my grandpa’s garage in the best way.

Why are there so many historic gas stations on Route 66? Back in the early-to-mid 20th century, car’s gas tanks weren’t as big as they are today! You needed to fill up way more frequently, so little stations popped up in every blink-and-you’ll-miss-it town across the Midwest and Southwest.

Murals

I love a good street art destination and I did not expect to find one in a small Midwestern town. But it turns out Pontiac, Illinois is a little famous for its murals! It was really nice to have a long break to stretch our legs and check out murals celebrating Route 66. There is another cute street art project they have with small painted car sculptures on street corners. My fave brings together Van Gogh’s most famous paintings on one miniature truck.

Black History on Route 66

Make sure you time your itinerary to arrive in Springfield, Illinois by 5:00 pm so you can tour the Route History museum. This was quite possibly the best attraction we visited on our entire trip, in large part because nobody else is doing this. Route History specifically explores the history of Black people along Route 66, digging into the history of the Green Book and sundown towns, using a virtual reality headset. Route 66’s heyday overlapped with the days of segregation and the museum’s virtual reality experience highlights so many aspects of segregation that get overlooked, as well as historic figures we really ought to know and celebrate for their community work.

Lincoln History

Even though Route History is, I believe, the best thing to do in Springfield, this city is better known as the hometown of Abraham Lincoln. His home is actually within walking distance right down the street from Route History. One of the nice things about this historic site is the National Park Service has preserved not just Lincoln’s home but the entire neighborhood, so it makes for a lovely, peaceful walk. There are also other historic homes in this area, such as the home of Julius Rosenwald, who provided lots of funding for African American schools between 1913 and 1932.

Drive-In Movies

For dinner, one of the classic Route 66 stops is the Cozy Dog Drive-In, home of the original corn dog. (This too was closed for Memorial Day weekend, so if you want or need an alternative, I can point you to Obed & Isaac’s Brewery.)

Here’s the real reason you want an overnight stop in Springfield, though: drive-in movies! This feels like such an essential road trip activity and Springfield is home to just one of two continuously operating Route 66 drive-in movie theaters. The movies are new releases, but the experience is a classic.

Where to Stay in Springfield

This is one of the few places along Route 66 that doesn’t really have an historic place to stay. Book any basic hotel room in your budget. We stayed at a Hilton Garden Inn and it was fine.

Day 3: Gateway to the West (Springfield, IL to Cuba, MO)

Today you’ll cross from Illinois into Missouri, complete with time at the Gateway Arch.

Lunch Stop in Litchfield

Litchfield is about 45 minutes south of Springfield and home to one of the oldest restaurants on Route 66, the Ariston Cafe. It’s not the most special dining stop you’ll make, but it’s convenient. You can skip the free Route 66 museum across the street – it’s mostly whitewashed local nostalgia and not a view of Route 66 as a whole.

World’s Biggest…

A classic gimmick for quirky roadside attractions along this stretch of Route 66 is the “world’s biggest.” Drive past the world’s biggest catsup bottle in Collinsville, Illinois.

Cahokia Mounds Side Trip

This is not a traditional Route 66 stop, but the Cahokia Mounds State Historic Park is just a few miles from the big catsup bottle in Collinsville.

Cahokia was a Native American metropolis around the 12th century and today, as a UNESCO World Heritage Site, it’s famous for its mounds. There is a great augmented reality app you can use as you walk around these constructed hills that will help you appreciate just how sophisticated the engineering of this expansive site truly was.

Sweet Treat

St. Louis, Missouri is just 15 minutes away and after a long outdoor walk around Cahokia Mounds, you’ll probably be ready for an ice cream break. Ted Drewes Frozen Custard has been serving up treats since 1929 and is a Route 66 must-stop. They have lots of St. Louis inspired flavors and their “Concretes” are basically what inspired the turn-it-upside-down Blizzards at Dairy Queen.

Gateway Arch

Soaring 630 feet over the St. Louis riverfront, the Gateway Arch is a longstanding icon of westward travel in the United States. If you want to take a tram to top, you will definitely need to plan way ahead and possibly get an earlier morning start. But even if you just go for the free museum and some photos in the park, this is a worthy stop. The gift shop here is also where you can buy a National Park pass if you don’t have one already.

Dinner in Cuba

Rather than stay overnight in St. Louis, I recommend moving a little further into Missouri to Cuba. Cuba, Missouri is another unexpected mural city and there are a few restaurants where you can get dinner. Frisco’s Grill and Pub is train themed with the most amazing wing sauce on their Gruffalo chicken sandwich.

Stay at the Wagon Wheel Motel

Here’s why you really want to stay in Cuba: your first historic motel. The Wagon Wheel is the oldest continuously operating motel on all of Route 66! Even better, its owner has painstakingly renovated it to one of the cutest motels on Route 66. They are so nice and welcoming and it’s a great start to the motel-heavy leg of your trip.

Day 4: Crossing Missouri (Cuba, MO to Tulsa, OK)

This is a heavy driving day and – I’ll be honest – the day when you are probably going to miss out on the most Route 66 attractions. It’s not because Missouri doesn’t have things worth seeing! But this 2 week Route 66 itinerary prioritizes more time in the Southwest than in the Midwest and some things had to get cut.

America’s First Drive Thru

A two-hour drive will get you to your second Springfield: Springfield, Missouri. Stop for lunch at Red’s Giant Hamburg. Though this is no longer at its original location, Red’s was the very first drive thru restaurant in America. The diner interior has just the right amount of kitsch and while the fries are a little soggy, their chicken and burgers are really good. (Fun Fact: It’s called “Hamburg” because they had to cut the “er” off their sign to fit it underneath power lines.)

For the Cars Fans

Another 90 minutes or so will take you into Kansas. Even though only a few miles of Route 66 cross through Kansas, they are a really packed few miles! Galena is a teensy former mining town that was one of the big inspirations for Radiator Springs in Pixar’s Cars. My little nieces were pretty delighted to get a pic from us with the “real” Tow Mater at Cars on the Route, a restore Kan-O-Tex service station.

Galena is also home to Gearhead Curios which is a worthwhile stop not just for souvenirs, but mainly to meet people who are passionate about Route 66 and get their tips.

A little ways down the road is Riverton, Kansas where a picturesque general store is a popular stop. The interior is honestly nothing special, but they have great prices if you need a bottle of water or a snack restock.

The Blue Whale

90 more minutes of driving stands between the Kansas leg and your next stop, the iconic Blue Whale of Catoosa. Though it is no longer used as a swimming hole, this big sculpture remains one of the most popular attractions on Route 66.

Dinner in Tulsa

Tulsa, Oklahoma is only 20 minutes from Catoosa. If you can make into the city by 5:00 pm, I definitely recommend a little souvenir shopping at Buck Atom’s curio shop. This is also where you’ll find one of the classic Route 66 Muffler Men statues!

For dinner, if you’re looking for an eatery with Route 66 history, you’ll find a classic diner at Tally’s Good Food Cafe. If you don’t mind something more modern, the Mother Road Market is Tulsa’s first food hall with a variety of local vendors offering everything from BBQ to international cuisine. 

Neon Sign Scavenger Hunt

Tulsa is famous for its old school neon and here’s why: they actually have a special citywide grant for the restoration of historic neon signs! It gives much of the city a very classic Route 66 feel. There is a small collection of signs in a weird tiny park down by the railroad tracks, but you can also drive down a long stretch of the actual historic Route 66 and see tons of neon. The giant Meadow Gold sign is – to my surprise – super cool in person.

Where to Stay in Tulsa

You’ll also find great neon at Desert Hills Motel, one of the nicest historic Route 66 motels in all of Oklahoma. Other good accommodations in Tulsa include The Campbell Hotel, a nicely restored boutique hotel right on Route 66 proper, and The Mayo, which is located in the city’s downtown Deco district.

Day 5: Neon Lights to Open Skies (Tulsa, OK to Amarillo, TX)

Brace yourself: this is the longest driving day of the entire Route 66 road trip. That’s because even though my own Route 66 itinerary included an overnight stop in Shamrock, Texas for the sake of less driving, that was a huge mistake. Our motel in Shamrock was not only really uncomfortable, but my poor spouse got devoured by bedbugs! (I don’t know how I escaped this fate and we took precautions to not carry any little insect hitchhikers.) So after crossing Oklahoma, I recommend only the briefest of stops in Shamrock and pushing on to a little more driving so you can enjoy a more comfortable stay in Amarillo. Route 66 road trip itineraries really require planning around where you want to stay and everything else fits in around that.

Lunch at the Rock Cafe

From Tulsa, you’ll drive to Stroud, Oklahoma for your lunch stop. The Rock Cafe has been serving travelers since 1939 and its owner was a big inspiration for Cars character Sally Carrera. We happened to visit on a day when their special was a frybread taco.

Barns & Soda Bottles

There are two great Route 66 stops in Arcadia, Oklahoma, which is less than an hour from Stroud. First on your right, you’ll spot the red Round Barn. This was constructed in 1898 and is highly lauded as an unusual piece of architecture. Like many other Route 66 attractions, it is much cooler in person than it sounds on paper.

A minute or two down and across the street is a newer addition to Route 66. Pops 66 is a modern gas station with a giant soda bottle sculpture nodding to a fun gimmick inside. They’ve collected a huge array of classic and quirky soda pops. Think bottles with vintage designs and every flavor imaginable from good old standards like root beer and cherry cola to really out there stuff like ranch dressing soda.

The Best Route 66 Museum

There are tons of small town Route 66 Museums along your road trip – at least one in every state. This is the best one to visit: The Oklahoma Route 66 Museum in Clinton. (And be careful about that location! There is another Oklahoma Route 66 Museum in Elk City.) The museum in Clinton has an excellent immersive experience covering the whole history of the Mother Road. Each room is themed around a certain decade. You’ll explore construction tools from the 1920s to diners from the 1950s and way, way more. Make sure you time your driving to arrive by 4:00 pm for enough time in the museum.

Jail Cell on the Border

Here’s a stop we wouldn’t have found without good paper maps and a heads up from a fellow traveler. Right on the Oklahoma-Texas border is a tiny town called Texola. Along a field off the beaten path, there is this little one-cell jail. Our friendly traveler claimed that this exact jail cell held Butch Cassidy and a number of other famed outlaws – I don’t really think that’s true, but it’s still a frickin’ cool photo op!

Dinner in Shamrock

While you should not bother staying overnight, Shamrock is still worth a stop for the Conoco Tower Station, an Art Deco gem that has been beautifully restored. Unfortunately, the attached U-Drop Inn Cafe is only open for breakfast and lunch most days, but there are a few other places to eat in Shamrock if you can’t make it all the way to Amarillo before dinner. Many of Shamrock’s restaurants are steakhouses, or you can grab a thin crust pizza at Rusty’s on 66.

Where to Stay in Amarillo

The Big Texan is a popular western-themed place to stay in Amarillo, but I would plan my own overnight stay at The Barfield hotel.

Day 6: Greeting the Desert (Amarillo, TX to Tucumcari, NM)

After all that driving across the beautiful plains of Oklahoma, you’ll be firmly in the desert for your first full day in Texas.

Barbed Wire Galore

Your itinerary actually starts with backtracking along Route 66 so you can visit the Devil’s Rope Museum in McLean, Texas. There’s no way to get all the way across Oklahoma on Day 5 in time to visit this museum between Shamrock and Amarillo, but it’s one of the best museums on Route 66! And you have plenty of time to head about an hour east of Amarillo to visit it.

I expected a quirky roadside attraction, but this museum is actually huge! As Americans settled the Wild West and set up ranches, barbed wire was an absolute necessity and cowboys developed so many different kinds of custom tools for creating it. There may have been more patents registered in this period of American history than any other time, all because of barbed wire taming the desert.

Lunch in Amarillo

Head back to Amarillo for a lunch break. Yellow City Street Food came highly recommended by local friends.

Palo Duro Canyon Side Trip

Just 20 minutes south of Amarillo is the second largest canyon in America. (The largest is of course the Grand Canyon.) The state park makes a nice drive to appreciate the scenery as part of your afternoon.

Cadillac Ranch

I was admittedly underwhelmed by this popular Route 66 attraction, a public art installation featuring ten half-buried Cadillacs covered in paint. You can bring or buy your own spray paint to add to the graffiti. Unfortunately, I find that the freewheeling nature of the attraction seems to empower people to be inconsiderate of one another and there are not any safety precautions taken around the spray paint. I saw one child who couldn’t have been more than 2 years old sent off to spray willy nilly without supervision. I’ve worked in immersive art before and this attraction ain’t it. Great pics, but not a genuine fun and creative experience.

The Oldest Diner on Route 66

The Big Texan gets a lot of attention, but there are other options for where to eat in Amarillo. The Goldenlight Cafe is on Amarillo’s historic 6th Street and is the oldest continuously operating diner on all of Route 66. It is just the right amount of divey and if you want an extra Texas spin on your meal, go for a buffalo patty on your burger.

Stay at One of America’s Last Motor Courts

Knock out one last long leg of driving after dinner so you can stay somewhere truly special to Route 66 history: the Blue Swallow Motel in Tucumari, New Mexico. The Blue Swallow is a little different to other motels – it’s actually a motor court. This special type of accommodations features enclosed garages next to each room. There are only five motor courts left in the United States!

Aside from this unique status, the Blue Swallow is one of the best places to stay along Route 66. The owners are so friendly and have made renovating it a passion project, keeping as many original 1939 features as possible from hardwood floors to bathroom tile to bedding and furnishings that resemble popular mid-century items.

Day 7: Side Trip to Santa Fe (Tucumcari, NM to Albuquerque, NM)

Traditional Route 66 paths diverge in this part of New Mexico and I suggest taking the longer northbound side trip up to Santa Fe before heading into Albuquerque. Santa Fe has a lot of historic sites, but if you need a break from all the history, I’ve got just the thing.

Fuel Up in Tucumcari

Before you leave Tucumcari, look for the iconic cow above Del’s Restaurant for a filling breakfast that is clearly popular with some local regulars.

Get Lost in Meow Wolf

Meow Wolf is the Disney World of immersive art and the House of Eternal Return in Santa Fe is where this national phenomenon got started. Embark on your very own portal fantasy as you weave your way in and out of this house through fridges, washing machines, and closets into otherworldly, larger-than-life landscapes. Tickets are super expensive but worth every penny as there is so much to experience and explore.

Early Dinner in Albuquerque

Albuquerque is a big craft beer town so an early dinner at a brewery is a nice introduction to the city. We went with Ponderosa which is very close to the Sawmill Market food hall, for a sweet paleta cap to the meal.

Sunset from Sandia Peak

One more worthy splurge caps off your itinerary today: the Sandia Peak Tramway. This is the longest tram in North America and the second longest in the entire world, spanning 3 miles up Sandia Peak, named for the watermelon pink color it takes on at sunset. Trams run every 15 to 30 minutes and boarding is first come, first served. Buy your tickets for a 5:00 to 8:00 pm arrival time and try to make sure you board close as close to sunset as possible. One more piece of advice: bring a warm sweater or jacket! Even in a light jean jacket, I was pretty chilly up on the mountain after sunset.

Where to Stay in Albuquerque

There are two great historic motels right next door to one another on historic Route 66. The Monterey Motel and El Vado Motel are owned by the same company and either is a nice accommodation for your Route 66 road trip. El Vado is more picturesque outside, but the interior at Monterey is super comfy. If nobody is staffing the check-in desk at one motel, you can go to the other’s office.

Day 8: Full Day in Albuquerque, NM

New Mexico’s largest city is the only one on this itinerary where you’ll spend more than one night. Between the desert scenery, the stellar museums, and the craft beer scene, I hope you’ll agree this is the best spot to slow down just a tad and explore more deeply.

Walk Among the Petroglyphs

Start your day with a little hiking before the desert temps spike. The Petroglyph National Monument is one of the largest petroglyph sites in North America with three big sections spread around Albuquerque. The most accessible is Boca Negra Canyon, which has paved trails, shaded seating areas, and about 100 petroglyphs, ancient Native American rock carvings. Many of the carvings are well labeled and it’s clear the park service worked closely with local tribes to educate visitors in a respectful way.

Tex-Mex Lunch Break

After freshening up at your motel, head across the street to Los Compadres. Out of everywhere I ate on this trip, this was the only restaurant where there was a significant wait thanks to a large crowd of weekly regulars. Get a taste of New Mexico’s famous green chiles with a plate of chiles rellenos and – local’s tip – get it with the red sauce.

Afternoon Museum Hopping

Two weeks isn’t quite enough time to include a pueblo day trip in your Route 66 adventure, but the Indian Pueblo Cultural Center is a fantastic introduction when you’re short on time. Between the museum exhibits written in first person and welcoming weekly dance performances, this center truly feels not like exotic voyeurism but genuine cultural exchange.

Albuquerque is also home to the National Museum of Nuclear Science & History, thanks to its proximity to Los Alamos, where the scientists of the Manhattan Project developed and tested the atomic bomb. Engaging exhibits cover the history and impact of nuclear science, atomic energy, the Cold War, and the unique marketing of the Atomic Age. (There’s even a nod to the Fallout video games inside.)

More of ABQ’s Craft Beer Scene

Just around the corner from the nuclear museum is the tongue-in-cheek named Bombs Away Beer Company, a veteran-owned craft brewery. Order up a sandwich for an early dinner alongside a pint or two. I like the unique and subtle orange peel, cardamom, and chamomile flavors of their Willie Pete Wit.

Day 9: Through the Painted Desert (Albuquerque, NM to Winslow, AZ)

Day 9 of your Route 66 journey takes you through the stunning landscapes of New Mexico and Arizona, ending in the historic town of Winslow. This day is filled with natural wonders, trading posts, and a step back in time to the glory days of Route 66.

Cross the Continental Divide

Your morning starts with a longer two-hour drive to Gallup, New Mexico right on the New Mexico-Arizona border. Just before you reach Gallup, you’ll cross the Continental Divide, a geological landmark where water flows toward the Pacific Ocean on one side and the Atlantic Ocean on the other. There is a marker on the side of the road for a quick photo op.

Lunch at El Rancho

This historic hotel has hosted countless Hollywood stars. Snap a pic or two of the stunning lobby, then hang a right for its restaurant where you can enjoy lunch surrounded by memorabilia from the hotel’s heyday.

Stop at a Trading Post

This section of Route 66 is peppered with famous trading posts. I wanted to try my best to find a place supporting Native artists rather than simply exploiting Native imagery and wound up at Yellowhorse just across the Arizona border. Maybe this was still the wrong call, but as far as I can tell, it is Native-owned. 

Given more time, I would detour to check out Cameron Trading Post, whose billboards caught my eye. Instead of the gimmicky “Moccasins for the whole family!” slogan that appears on most other trading post advertisements, Cameron’s billboards have a distinct “Come and learn from us” message.

Colorful Sands and Crystal Trees

About one hour from Gallup is the Petrified Forest National Park, which is home to not only vast petrified wood collections but also the Painted Desert. There are several short loops to explore around the park, each with more otherworldly landscapes than the last. Plan on about 45 minutes worth of driving and add more time depending on how much you’d like to hike.

Dinner in Holbrook

Romo’s Restaurant in Holbrook, just a few minutes from the Petrified Forest, is a mainstay on Route 66. Fill up on hearty, delicious Mexican food and don’t skip the giant margaritas they serve up in perfectly kitschy cactus glasses.

Where to Stay in Winslow

It’s only 30 minutes from Holbrook to Winslow, Arizona of “Standing on a corner” fame. While, yes, there is a little park for your Eagles selfie, the real reason to come to Winslow is so you can stay at La Posada. This beautifully restored 1930 hotel was designed by Mary Colter – basically the Frank Lloyd Wright of the Southwest. Its sprawling grounds and gardens are a lightly Gothic dream.

Day 10: Grand Canyon Day Trip (Winslow, AZ to Flagstaff, AZ)

Even though it’s not officially ON Route 66, no trip down America’s Main Street is complete without a detour to one of the most breathtaking natural wonders in the world: the Grand Canyon.

Breakfast in Winslow

The morning light is a little better than the evening for a photo op at Standing on the Corner Park, so pop over there first thing. It’s just down the street from La Posada. Then, fuel up on a fab breakfast at the hotel’s Turquoise Room.

First View of the Grand Canyon

Grand Canyon National Park is about two hours from Winslow, so you’ll be arriving mid-afternoon and staying through sunset. Get your first glimpse of the unbelievably vast landscape at Mather Point, just a few minutes’ walk from the main visitor center. Pack lunch or grab a bite to eat inside the park – Harvey House Cafe is a convenient pick.

Hike Part of the Canyon

Bright Angel Trail is one of the best introductions to Grand Canyon hiking you can get. While a brief afternoon isn’t enough for the full trail, you can head down about 1.5 miles and use the first rest stop you encounter as your milestone to turn around and head back uphill. It is very easy to underestimate the canyon, even for experienced hikers! If you need a more accessible hike, the Rim Trail has great views too.

Watch the Sunset

When it’s time for sunset, even just 15 minutes of walking can help you avoid the crowds at Mather Point. Instead, you’ll set up at Yavapai Point to watch the magical shifts in color and light as the sun sets over the canyon.

Where to Stay in Flagstaff

A little over one hour south of the park is the city of Flagstaff. High Country Motor Lodge isn’t an historic Route 66 motel, but it has a unique hipster-meets-vintage vibe and quite possibly the comfiest beds in the country. 

Day 11: Vintage Vibes in West Arizona (Flagstaff, AZ to Kingman, AZ)

After a tough day hiking, you’ll want to take it easy. So to make up for those long days crossing Missouri and Oklahoma, this day of your Route 66 itinerary only includes about two hours total of driving.

Soak Those Sore Muscles

High Country Motor Lodge isn’t just a good night’s sleep. It also has a Nordic spa perfect for a little relaxation and rejuvenation before you continue the road trip. When you book your spa time, you’ll get private access to a little sauna and fire pit. Between sauna jaunts, you’ll pop out to the hotel’s pool for a cold plunge and the jacuzzi to soak. It’s an excellent start to one of the more relaxed days of the trip.

Lunch in Seligman

Seligman is one of those classic Route 66 small towns. Delgadillo’s Snow Cap is a beloved eatery famous for its playful atmosphere and delicious burgers and shakes. The founder Juan Delgadillo was instrumental in preserving the spirit of Route 66 after the federal government decommissioned the official highway.

General Stores Galore

Both Seligman and nearby Hackberry are home to quirky shops full of Route 66 memorabilia. Seligman Sundries, the Rusty Bolt, and the Hackberry General Store are all treasure troves of nostalgic items.

Dinner in a Diner

Only an hour of driving lies between Seligman and Kingman, so take your time to relax and lounge about the motel (see below). When you’re ready for dinner, Mr D’z is one of the most famous and popular diners on the Mother Road. Its checkerboard floors and bright teal and pink paint job are such a vibe. It’s really something from a bygone era – they even make their own root beer!

Make sure you stay until after dark so you can enjoy Kingman’s collection of neon signs – the best I’d seen since Tulsa.

Where to Stay in Kingman

While it’s not as lavish as El Rancho back in New Mexico, the El Trovatore Motel has just as storied a list of past guests. Don Knotts, Bob Hope, Jane Russell, Marilyn Monroe… there are even rumors that Elvis stayed here! The owners and staff are super knowledgeable about Route 66 history and very welcoming.

Day 12: Ghost Town Excursion (Kingman, AZ to San Bernardino, CA)

This slice of desert is home to a ghost town or two. I’ve been to both Oatman, Arizona and Calico, California, so I’m going to save you some time and tell you to skip Oatman in favor of Calico!

Lunch Stop in Needles

About one hour from Kingman, just over the California border is the town of Needles. Even though it makes for an early lunch stop, you need to learn about the fascinating Route 66 history of Harvey Houses. The El Garces Intermodal Transportation Facility is a restored former Harvey House and a great introduction to one of the old roots of American hospitality. The Wagon Wheel Restaurant also dishes out Route 66 nostalgia.

Get Your Wild West On

After skirting the southern edge of the Mojave Desert for two hours, you’ll reach Calico – my ghost town of choice. Originally built as a mining town in the 1880s, Calico was restored by Walter Knott of Knott’s Berry Farm fame. This makes Calico a little theme park-y, yes, but the payoff is an attraction with nicely restored historical buildings, no cars in the way of your photos, higher quality shops with nods to history, and a friendly attitude toward customer service. The sum total result is that, while Oatman, Arizona may have donkeys, walking around Calico feels the way you always imagined the Old West would feel.

Quirky Art Installation

Were any other ‘90s kids hopelessly enamored with that scene in Harriet the Spy where Rosie O’Donnell takes the kids to a yard full of colorful glass bottles turned into art? That’s a real place and while the movie location is in Austin, Texas, there’s a really similar installation in southern California: Elmer’s Bottle Tree Ranch in Oro Grande! This whimsical roadside attraction features hundreds of “trees” made from glass bottles and metal. It’s a quirky and colorful stop that’s perfect for photos and pretending you’re Michelle Trachtenberg.

Dinner in San Bernardino

Don’t spend too long getting lost among Elmer’s upcycled forest. You want plenty of time to battle the SoCal traffic and arrive in San Bernardino no later than 6:30 pm so you can enjoy dinner at Mitla Cafe. This local institution has been serving up tacos, enchiladas, and other Mexican favorites since 1937, but it’s not just a Route 66 favorite – this restaurant is supposedly the inspiration for Taco Bell! Between this and the small museum inside the first ever McDonald’s, San Bernardino is basically America’s fast food central.

Where to Stay in San Bernardino

Controversial at best, but yes, I stayed in a Wigwam Motel. There is a lot to be said about the exploitation of Native American imagery in U.S. culture, and at the same time, much of it is very deeply embedded in our culture. While I will take a hard pass to buying a neon-dyed dreamcatcher from a white-owned souvenir shop, I did still stay in a Wigwam Motel. 

If you’re interested in doing the same, I recommend leaning into it as a teaching moment. Don’t treat these concrete “tepees” as an authentic reflection of indigenous culture – they’re not. What they are, however, is a specific kind of mid-century Americana that used Native-inspired iconography while often simultaneously mistreating Native peoples. 

A total of seven Wigwam Villages were built across the country between 1936 and the 1950s. The San Bernardino location is one of three remaining, and is reportedly better kept than its counterpart in Holbrook, Arizona. There aren’t a ton of historic Route 66 accommodations in this stretch of the road trip, and – for better or worse – Wigwam Motels were part of the Mother Road’s history.

Day 13: The End of the Road (San Bernardino, CA to Santa Monica, CA)

It’s your final day of driving! Are you ready for the celebratory finish at the Pacific Ocean?

Small Towns of San Gabriel Valley

I’m a huge Crazy Ex-Girlfriend fan and even though West Covina itself isn’t on Route 66, a lot of the small Southern California towns that are on the Mother Road get frequent nods throughout the show. If you stick to the freeways, a drive from San Bernardino to Santa Monica could take less than two hours. But you can stay off the freeways and watch Route 66 stitch together small towns like San Dimas, Monrovia, and Rancho Cucamonga.

Rancho Cucamonga is deserving of a stop for the Cucamonga Service Station. This hidden gem was originally built as a gas station in 1913 and the community came together on its centennial to restore it. There’s now a tiny museum run by passionate volunteers. Their souvenir corner also boasts magnets for some very niche Route 66 attractions, which was cool to see.

For a lunch stop, Le Roy’s in Monrovia offers up the 1970s brand of 66 retro along with the absolutely most massive serving sizes I think I’ve ever seen.

Pass through Los Angeles

As you get closer to the end of the road, depending on time and traffic, you might want to make stops at Griffith Park or the Hollywood sign. The closer you get to late afternoon though, the better off you’ll be to hit the freeway and make a beeline for Santa Monica.

Santa Monica Pier

You’ll wrap up your trip at the vibrant, bustling Santa Monica Pier. There is an official End of Route 66 sign, and the rest of the pier will keep you well occupied for the evening. There’s an historic merry-go-round and a brightly flashing arcade, as well as plenty of places to eat. One of the nicer choices is The Albright which has lots of seafood options, including great fish tacos. After dinner, head to Pacific Park for classic rides and games. A trip on the iconic ferris wheel is non-negotiable.

Where to Stay in Santa Monica

Celebrate a successful two weeks on the road with the splurge to end all splurges: a night at the Fairmont Miramar Hotel. This luxe beachfront hotel has welcomed weary Route 66 road trippers since the highway’s earliest days. Originally an 1880s mansion, the property was converted to a hotel in the 1920s and became a bit of a Hollywood darling – Greta Garbo lived here for four years! A lavish lobby and impossibly cushy bed are your just reward for all that driving.

Day 14: Fly Home

The final day of your two weeks is for getting home. You’ll fly out of LAX and if you’re smart enough to book an early flight, you can make it to the airport in a mere 20 to 30 minutes.

How to Plan a Longer Route 66 Trip

If you have more than two weeks, consider spending extra days in key cities like Chicago, St. Louis, and Santa Monica, as well as breaking up those long drives across Missouri and Oklahoma. You can also take more detours to explore nearby attractions or enjoy a more relaxed pace. I’m already dreaming of the long-term travel version of this trip!