10 Diners In 10 Days: A Route 66 Roadtrip

Remember - for the full experience with turn-by-turn directions to each stop, check out "10 Diners In 10 Days: A Route 66 Roadtrip" on the outRise app!

 

What’s more American than a roadside diner? How about Route 66.

“10 Diners In 10 Days” is an epic 10-day experience on one of America’s oldest and most iconic roadtrips - Route 66 - while enjoying an American classic - diner grub

You’ll stay at classic hotels (and in some cases - wigwams), visit abandoned ghost towns, quirky roadside shops and so much more! 

This blog is to help you bring this dream to life. Below you’ll see a quick breakdown of down you'll visit, driving distances and recommended hotels that you can book beforehand if you’d like. Or - you can always wing it!

Hotel Reservations In Advance (optional)

Day 1 - Chicago, IL > St. Louis, MO (300 miles)

Unique Option

The Cheshire

Economic Option

Red Roof+ St. Louis - Forest Park

Day 2 St. Louis, MO > Carthage, MO (280 miles)

Recommended Stay

Boots Motel

Other Unique Option

Grand Avenue B&B

Day 3 Carthage, MO > Edmund, OK (230 miles)

Unique Option

Wangship Palace

Economic Option

Executive Inn (Edmund)

Day 4 Edmund, OK > Shamrock, TX (180 miles)

Unique Option

Hotel Townhouse

Economic Option

Route 66 Inn

Day 5 Shamrock, TX > Tucamari, NM (210 miles)

Recommended Stay

Blue Swallow

Economic Option

Bright Morning Motel

Day 6 Tucamari, NM > Albuquerque, NM (200 miles)

Unique Option

Bottger Mansion Of Old Town

Economic Option

Rodeway Inn Albuquerque

Day 7 Albuquerque, NM > Holbrook, AZ (240 miles)

Unique Option

Wigwam Motel #6

Other Option

Brad’s Desert Inn

Day 8 Holbrook, AZ > Kingman, AZ (240 miles)

Unique Option

Hotel Brunswick Suites

Economic Option

Motel 6 Kingman

Day 9 Kingman, AZ > San Bernadino, CA (280 miles)

Recommended Option

Wigwam Motel San Bernardino

Economic Option

Rodeway Inn (San Bernardino)

Day 10 San Bernadino, CA > Santa Monica, CA (78 miles)


10 Diners In 10 Days: A Route 66 Roadtrip

Day 1

 

Starting Things Off 

This trip kicks off in the heart of downtown Chicago - The Loop. The official starting place of Route 66 is at Adams & Michigan Ave, which is conveniently located right next to the Millennium Park (and the Bean). Heads up - this place can get PACKED in the summertime, and if you find yourself starting this trip on a weekend day in summertime, you may search for an hour before finding parking. But, if you get lucky and find some parking, this is one of Chicago’s best waterfront parks, and you can go for a stroll along Lakefront Park before hitting the road.

Diner 1: Launching Pad

Just over an hour outside the hustle of downtown Chicago, Launching Pad kicks off your Route 66 diner adventure with a humble hotdog-stand-turned-Route-66-staple (yes, that’s all one word). It features a Route 66 Welcome Center, gift shop and of course, an awesome little diner. There’s actually a ~30 ft. spaceman out front to commemorate the US-Russia space race which, having been constructed in 1956, Launching Pad lived through.

An American Beer

OK! You’ve done a bit of driving today and have found yourself in St. Louis, MO. So how do you reward yourself? How about a tour of the Anheuser-Busch factory to see how America’s favorite beer is made! This is Anheuser-Busch’s flagship brewery where they offer free tours (which include a glimpse at the famous Clydesdales) that include a free pint!

Explore St. Louis

There’s a couple very cool nearby hotels, including the Cheshire and the Lemp Mansion, and many more. But regardless of where you stay, this area of St. Louis is fantastic, and I highly recommend you check out the Clifton Heights area, which is home to an amazing Italian-American community.

 
Hotels

Unique Option

The Cheshire

Economic Option

Red Roof+ St. Louis - Forest Park

 

Day 2

The Ozarks

Today you’ll drive across the entire state of Missouri. You have about a 4 hour drive ahead of you, and I highly, highly recommend stopping at the Mark Twain National Forest to break up your drive. You’re in the middle of the Ozarks after all! If you’re up for a long one, the Barryman And Ozark Trail is an easy, 7 mile hike through the Ozark Mountains that offers breathtaking scenery. If you’re in the mood for a shorter jaunt, the Kaintuck Deer Trail is an easy, two-mile loop a little further down Old Route 66.

Diner 2: Iggy’s Diner

Just north of old Route 66 is Iggy’s - it’s been around since Route 66 and this greasy spoon is where you’ll find the perfect post-hike meal of biscuits and gravy, milkshakes and great greasy - juicy burgers. You’re not on diet - right?!

Check-In To A Route 66 Stalwart

Alright! You’ve made it to the other side of Missouri, and hopefully you got to experience the beauty of the Ozarks along the way. The Boots Motel is a Route 66 stalwart, and interestingly enough it was built in the nation’s worst economic downturn on record - the Great Depression. It started as a gas station but transformed into one of the highway’s most prominent hotels after being saved from demolition by two sisters who love Route 66. 

Drive-In & Chill

After grabbing a shower, time for a little Americana. Like, $8/double-feature type of Americana. It’s awesome. Plus the concession stand (just hearing the word “concession stand” brought back some serious nostalgia) has hot dogs, sodas and popcorn. It’ll remind you of what sneaking out during high school felt like (;

Hotels

Other Unique Option

Grand Avenue B&B

 

Day 3

Old-School Highway Pit-Stop

Nelson’s Old Riverton Store has been around since Route 66 was formally established as Route 66. It’s your classic, down-home country store, except that’s it’s chock-full of quirky, rich, early-Americana history and memorabilia.

Diner 3: Pop’s Soda Ranch

Whether you call it “pop” or “soda” gives us great insight into where you’re from (and whether you’re a good person - “pop” is the correct answer :p ). But whatever you call it, Pop’s Soda Ranch (also known as Pops 66) has 700 different kinds of sodas and sparkling waters. And to top it all off, there’s a 66-foot soda figurine out front too! You may also want to check out the nearby Route 66 roadside attraction, the “Arcadia Round Barn”.

Oh, and if you stay at the nearby town of Edmund, you HAVE to go check out Arcadia Lake - it’s gorgeous, and the perfect place for a great sunset.

But if you want a bigger city experience - head to Oklahoma City to stay!

bigstock-Route--In-The-Desert-With-Sc-413551880 (1)

Hotels

Unique Option

Wangship Palace

Economic Option

Executive Inn (Edmund)

 

Day 4

Diner 4: Route 66 At The Market

Route 66 Diner At The Market is one of the more refined diners you’ll stop at along the route - but a diner nonetheless! Route 66 At The Market is a great little diner that makes for a great pitstop along the way.

No Place Like Texola

Just before crossing into Texas, you’ll hit Texola. Texola is the small, kitchy, western American town you think of when you think of Route 66. While it’s hayday was 1930 (a whopping 581 residents), by 2010 that number had dwindled to just 36. Still though, Texola is a very cool town to visit on your drive through Route 66. Two musts in Texola; the tiny stone jail and the Magnolia Service Station.

My actual favorite part of driving through here is seeing how nature just reclaims the human world in less than 100 years. So many abandoned structures and it’s fascinating to see trees growing out of them.

Hotels

Unique Option

Hotel Townhouse

Economic Option

Route 66 Inn

 

Day 5

Cadillac Ranch

Like so many things on Route 66, Cadillac Ranch has a weird history. It started when a bunch of hippies came from San Francisco to Amarillo and wanted to shock the local Texas population with art. So, they buried some Cadillacs up to their halfway point, in an ode to the Cadillac tailfin. 

Texans responded in kind, by stopping along the highway to get out and ensure the cars were meticulously and thoroughly defaced.

Instead of fighting it, the hippies embraced it (as they tend to do), and it soon became an art haven where, even today, people spray paint the half-buried Cadillacs. It is one of those amazingly quirky, amazingly unique stops along Route 66 that you have to do in order to make it a complete trip.

Diner 5: Midpoint Cafe

A little under an hour of driving takes you to Adrian, Texas for a stop at the historic Midpoint Cafe. Midpoint bills itself as the official Route 66 halfway point between Chicago and Santa Monica, and your menu is as standard American as they come!

The Blue Swallow Motel

The Blue Swallow Motel is located in Tucamari, New Mexico and is a Route 66 stalwart. This hotel has been located on Route 66 since it opened in 1940, and although it’s been restored, it gives you that retro Route 66 vibe you’re definitely looking for.

And hey - if you have some free time - be sure to grab dinner from Watson’s BBQ & head to Tucumari Lake for a sunset!

Hotels (other options)

Economic Option

Bright Morning Motel

 

Day 6

Diner 6: 66 Diner

Today’s a long stretch of desert driving. 220 miles from the Blue Swallow Motel is the 66 Diner - once a gas station and renovated to be a modern day diner, it’s a full-on retro-themed stop, complete with burgers, shakes, jukeboxes and more. It’s full-on old-school diner style - the coral-blue chairs and bar stools, the tile floors...you’re going to love it.

Explore Albuquerque

Albuquerque is, in my opinion, one of the most underrated towns in America. Take a stroll down Central Ave, check out the International District and head to Tingley Beach to catch a sunset over the Rio Grande.

Hotels

Unique Option

Bottger Mansion Of Old Town

Economic Option

Rodeway Inn Albuquerque



Day 7

Diner 7: Route 66 Railway Cafe

Today’s quite the drive, and Route 66 Railway Cafe is a great way to break it up. Honestly, this place looks like a 50’s farmhouse that you plopped right into present-day America. Doesn’t make sense? Doesn’t have to - I’m telling you, that’s how it feels when you walk in. SUPER friendly staff, service you can’t beat and real down-home cooking. If you can make it for breakfast - that’s the best time to go!

Painted Desert Inn National Historic Landmark

Today you’ll make your way into Arizona, where you’ll hit Petrified Forest National Park, and this is actually the only national park in the country that protects a portion of Route 66. It has American Indian ruins and some fossils that span 200 million years into the past. And while the national park is something special, you need to check out the Painted Desert Inn.

It was once a dessert inn that provided hospitality to Santa Fe Railroad travelers, and did very well...for 2 years. In 1942 the US went off to war, and the Painted Desert Inn closed. But it has since been restored, and today you’ll be able to see it as it originally was - a stop for wayward and weary travelers battling the unforgiving desert of the American southwest.

Wigwam Village Motel

Wigwam Village Motel #6 one of only 3 remaining wigwam hotels - and you’ll hit two of them along Route 66 (you’ll be able to stay at this one and the other one, located in California). Today, it’s listed on the National Register Of Historic Places and still run by the same family that opened it up in the 50’s.

It’s a hotel room, in the shape of an American Indian wigwam, with all the amenities of a modern hotel. Pretty cool - wouldn’t ya say?

Hotel

Other Option

Brad’s Desert Inn

 

Day 8

Diner 8: Rutherford’s 66 Family Diner

You’ll notice a trend here. The further west you go, the longer the drives are. Makes for a really great Route 66 experience if you ask me. 

You’ll pass through both Winslow and Flagstaff on your way out here, and this is a great time to stretch your legs and explore these two really cool towns.

A 3.5 hour drive from Wigwam Village Motel is Rutheford’s 66 Family Diner. The memorabilia and decor of this place SCREAM old-school Route 66, and the food and service add that much more to the experience. Get yourself a side of onion rings there kido!

Hotels

Unique Option

Hotel Brunswick Suites

Economic Option

Motel 6 Kingman



Day 9

Diner 9: Mr. D’s Route 66 Diner

Mr. D’s Route 66 Diner is the place to start your day. Seriously. Got cheesy 50’s roadtrip music to make you feel like you’re in a movie? Play it - the setting of this place is enough to make you feel just that.

Mojave National Preserve

Take a pit stop in the Mojave National Preserve. It’s absolutely otherworldly - 1.6 million acres of desert wilderness to hike, drive and explore. 

Wigwam Hotel

One of the other remaining 3 wigwam hotels in the US - this is where you’ll spend your last night on Route 66! This hotel is much more “California” - the room interiors are more updated, it’s a bit more modern, and there’s even an outdoor pool to enjoy! 

Hotels (other options)

Economic Option

Rodeway Inn (San Bernardino)

 

Day 10

Diner 10: Molly’s Cafe

You’ve almost made it! One more diner to go. You’ll need to backtrack a tiny bit from the Wigwam Hotel, but it’s worth it. Molly’s Cafe is a classic Route 66 stop, complete with the memorabilia, delicious cooking and down-home service that you’ve come to expect over the past couple weeks!

Santa Monica Pier

You did it! You made it from head to tail on Route 66, and ate your way through the heart of the country doing it! Get a picture with this sign, stick your toes in the water and enjoy yourself and the sunny California sun. 

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