Route 66: 14 day road trip itinerary

For many people planning a Route 66 road trip it can get a bit overwhelming. I totally get it, have been there and got the t-shirt! Checking some sample plans of how to do the trip can help get your head around it and give you a good start when planning your own journey.

That’s where this Route 66 14 day road trip itinerary comes in. I’ve written it as a sample journey from the very beginning of the road in Chicago all the way to the Pacific Ocean.

I hope that you’ll find this road trip itinerary helpful no matter how long you have for your road trip.

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old truck on route 66

A note from the writer: Hey! I’m Kirsty and I’m a Route 66 enthusiast – I first became obsessed almost 20 years ago and then first visited in 2014. I’ve recently just come back from my last trip too! Comment below if you have any questions about your road trip and I’ll get back to you ASAP – or join me in my free FB group here.

Are you thinking of planning a road trip? I highly recommend a guide book to explore all the attractions around. It’ll come in handy when you’re actually driving too (if you get one with directions!)

My favorite for the planning stage is the Route 66 Adventure Handbook

Planning your 2 week Route 66 road trip

Before we get started with the itinerary let’s take a look at some questions you might need to consider when you’re planning this journey:

Is 14 days enough for a Route 66 road trip?

So one of the first questions that I get asked is whether 14 days is enough to do the road trip.

Yes, you can do Route 66 in 14 days. Your driving mileage will vary each day from 100 – 250 miles and you’ll move on to a different destination each day.

I’d definitely be aware of the fact that it’s quite an intense driving time. You’re going to be moving on every day and you won’t have time to do side trips or to enjoy the cities of LA and Chicago at either end. But, yes, 14 days is definitely doable!

Will 14 days be a good amount of time to do Route 66?

So we’ve established that you can do Route 66 in two weeks, but should you? Are you going to do it well or will it be a terrible time?

I think the sweet spot for a Route 66 trip is between 2 and 3 weeks so a 14 day stretch fits in there nicely. You can definitely have a good time, you might wish you had more time to explore, but hopefully that will just encourage you to come back again!

How much driving will you do each day?

With a 14 day road trip on Route 66 you’ll be driving for between 100 and 250 miles each day. So some days might only have an hour or two on the road and some days will have longer driving days that you might want to break up throughout the day.

Should you book your accommodation in advance?

This is a personal preference. I know many people like to keep their options open and see what is available when they arrive. I, personally, am not like that and I much prefer to have my bed booked!

Some of the accommodation suggested on this page are popular stops on the road and as such, especially if you’re traveling in high season, you might be wise to book in advance.

Lots of hotels offer a decent cancellation policy these days so if your plans change it shouldn’t be an issue but always check when booking, especially if you’re booking direct with them.

Renting a car for route 66?

Most people think about renting a car for their Route 66 trip simply because the distances are so vast and it makes sense in a financial sense and also when thinking about the time available.

I’ve written a post about some tips you might find useful for booking your Route 66 rental car but checking out comparison sites like Discover Cars is my top tip to get a good deal.

sign on road bridge on Route 66 in Kansas
Are you ready for an epic trip?

Route 66 14 day road trip itinerary: overview

All mileage is approximate and is gleaned from Google Maps which will take the Interstate rather than the actual Route 66 alignments.

1 Chicago0
2Chicago – Springfield, IL250
3Springfield, IL – Cuba, MO180
4Cuba, MO – Baxter Springs, KS215
5Baxter Springs, KS – Chandler, Ok165
6Chandler, OK – Shamrock, TX210
7Shamrock, TX – Tucumcari, NM205
8Tucumcari, NM – Santa Fe, NM175
9Santa Fe, NM – Gallup, NM200
10Gallup, NM – Holbrook, AZ100
11Holbrook, AZ – Kingman, AZ237
12Kingman, AZ – Barstow, CA206
13Barstow, CA – Santa Monica, CA130
14Santa Monica, CA0

Day 1: Chicago

Miles to drive: 0

Our first day is spent in the city of Chicago. If you’re flying in to the city then much of today might be getting settled in to your hotel and exploring a little.

The beginning point of Route 66 is on East Adams Street right by the Art Institute of Chicago. If you’ve never been to Chicago then a river cruise could be a good way to get a fun overview of the city architecture, history and sights.

So many eating options here – for a good Chicago style pizza that is on the road itself try out Giordano’s on W Jackson Blvd.

Accommodation options for day 1

While you have the entire city of Chicago at your disposal, I suggest a hotel in the Downtown/South Loop area. If you want to start your Route 66 trip from the very beginning point it’s good to be in the vicinity so that you’re not fighting with traffic. Do be aware that they may have hefty car park charges and budget them in accordingly.

Alternatively you could aim for a hotel with a river view – a little bit of luxury before using the more basic motels that are ahead of you!

Route 66 mural in Pontiac

Day 2: Chicago, IL – Springfield, IL

Miles to drive: 250

Before leaving Chicago this morning try out Lou Mitchell’s for breakfast. It’s been a Route 66 classic since the beginning!

You’ll pass through many small towns on your way through Illinois with attractions like the Gemini Giant and lots of restored gas stations.

Head to Pontiac for some interesting museums about the history of the cars from round here. For lunch why not try Edinger’s Filling Station, a retro style diner nearby.

Your destination for today is Springfield, the former residence of President Lincoln. There’s a lot to do, including visiting his home, but do be aware of opening times if you wish to visit. You could always choose to visit in the morning before leaving the city. It’s normal opening times are 9am-5pm.

For food in the evening you could check out the Cozy Dog Drive In – a historic diner that’s been on the road since 1949.

Accommodation options for day 2

Springfield is a city and as such has a wealth of options. Any chain you wish will have a hotel here. For something a little different and local I suggest:

Murals on Route 66 through Missouri

Day 3: Springfield, IL – Cuba, MO

Miles to drive: 180

While around 3-4 hours driving today you need to make a decision as to whether you’ll spend time in the city of St Louis or explore some of the small towns in Illinois and Missouri.

If you want to go to St Louis then a trip up the Gateway Arch is a must and you can learn about the westward expansion in the museum. A trip on a boat on the Mississippi shouldn’t be missed too.

As you leave St Louis be sure to check out Ted Drewes frozen custard spot, you’ll be glad, especially if it’s a warm day!

You’ll end your day in Cuba which is has a lot of murals around to check out and a quirky BBQ restaurant called the Missouri Hick Barbeque which might make a good evening meal option.

Accommodation option for day 3:

A fantastic historic motel that’s been going since the 30s – it’s a popular one so a good idea to book ahead of time. Cuba has a few other options if you don’t fancy this one with some chains and other budget motels in town.

Historic filling station in Missouri on route 66

Day 4: Cuba, MO – Baxter Springs, KS

Miles to drive: 215

You’ll travel through most of Missouri and into Kansas today, yes all 13 miles of it in the Sunflower State! There’s a lot to see in Missouri from caverns to museums and giant roadside attractions. Some notable places for you to try not to miss are Lebanon and the retro garage, Gay Parita, in Paris Springs.

Kansas attractions are plentiful too so make sure you leave time to explore some of them. You’ll end your day in the town of Baxter Springs, a really nice place with civil war history and mining heritage.

Accommodation option for day 4:

Day 5: Baxter Springs, KS – Chandler, OK

We cross over into the next state to see what Oklahoma attractions are around!

You’ll also drive through the city of Tulsa which has a number of things to do as well. Again you might need to make a decision as to whether you’re interested in the smaller towns and sights or whether you want to explore the city.

Whatever you decide, be sure to stop at the classic Blue Whale in Catoosa to get that classic photo opp.

Before you rest your head a good eating option is in the town of Stroud, just before Chandler. The Rock Cafe is a classic Route 66 diner that was one of the inspirations for the Disney Cars film – the owner is said to be Sally!

Our evening destination is Chandler – an interesting town with some museums about the history of Route 66.

Accommodation option for day 5:

Day 6: Chandler, OK – Shamrock, TX

Oklahoma has a lot to offer the Route 66 traveler so you’ll be pleased to have some more time in the state today before crossing over in to Texas.

Oklahoma City is the big city you’ll pass through today.

Shamrock is the first town you find on Route 66 through Texas and it’s a stunner. We were drawn here by the Irish connection (my husband has Irish roots) but we really loved the town and the neon – really feels like a proper Route 66 town! For evening food try Rusty’s where you’ll find classic burgers and fries.

Accommodation option for day 6:

There are a few options in Shamrock and all close by to the U drop Inn for that neon magic in the evening.

Day 7: Shamrock, TX – Tucumcari, NM

Miles to drive: 205

Before leaving Shamrock be sure to take a look around the U-Drop Inn in daylight. The cafe is apparently opened back up now so you might be able to catch a bite to eat here too.

The Lone Star State has a lot of wide open spaces for that road trip vibe but also lots of Texas road side stops too including The Big Texan (do you have space to try and eat their giant steaks?), the Cadillac Ranch and also the Mid Point. The city of Amarillo is worth a stop if you can, it’s not as big as other cities on Route 66 so doesn’t feel as overwhelming!

Tucumcari, just over the border into New Mexico marks a new chapter but continues the neon filled evenings that you had the previous night. For food options try either Del’s Restaurant or La Cita.

Accommodation option for day 7:

Tucumcari has a number of motels that are perfect for Route 66 travelers – and the joy is that you can enjoy them all from the outside as their neon lights up.

overlooking Santa Fe in New Mexico

Day 8: Tucumcari, NM – Santa Fe, NM

Miles to drive: 175

Route 66 in New Mexico has two very different alignments and the original one went through the city of Santa Fe. A few years later it had a much more direct route. For this itinerary we’re heading slightly north and exploring round the New Mexico attractions there!

You’ll be driving along some of the roads that mirror the Santa Fe trail. An interesting stop is the Pecos National Historical Park with some old ruins and trails to get you out and about in nature.

Santa Fe itself is worth spending time in with plenty of museums, good eating options and nightlife if you want something a little different.

Accommodation option for day 8:

Santa Fe is a little more expensive than some of the other towns you might be staying at on Route 66. The motel El Rey is a good, relatively inexpensive option or you could splash out and enjoy a hotel downtown.

El Rancho Hotel New Mexico

Day 9: Santa Fe, NM – Gallup, NM

Miles to drive: 200

After the city of Santa Fe you also have the city of Albuquerque nearby too. You can choose to spend today exploring that city, including its historic centre or you could choose to spend your time in the smaller towns checking out the abandoned businesses and cars.

The Petroglyph National Monument is a nice stop if you need to stretch your legs today and get a stunning view over Albuquerque while also seeing history in front of you.

If you have time, Grants has a great mining museum that covers a lot of the interesting industry in these parts including uranium mining!

Make sure to take some time in Gallup itself to check out the Cultural Centre and learn about how the amazing Navajo people contributed to the war effort by being able to send coded messages.

Accommodation option for day 9:

Your last night in New Mexico is in Gallup not far from the state border. This historic hotel hosted many a Hollywood star back in the day!

Day 10: Gallup, NM – Holbrook, AZ

Miles to drive: 100

Our shortest driving day but this is because we’re going to be driving through a National Park and it’s well worth exploring rather than driving straight through.

The Petrified Forest is a great option whether you’re ultra fit and love to go on hikes or if you’re not and don’t want to stray far from your car. You can drive around the park, stopping at various points to take in the scenery and learn about the history of the area.

Holbrook is not far from the park and if you’re still enthralled by rocks, fossils and gemstones you’ll find lots of shops to explore. For food options try the Butterfield Stage Company Steakhouse.

Accommodation option for day 10:

Holbrook is home to one of the most iconic motels on the road – the WigWam motel. It’s a basic option but a must for many people. There are also a few other options in town if you don’t want to stay there.

Day 11: Holbrook, AZ – Kingman, AZ

Miles to drive: 237

We’re driving pretty much across the whole of the state today so it’s probably a good day to get up early to see if you can fit in as many Arizona attractions as possible.

It feels odd to not encourage you to check out the Grand Canyon while driving by – you really need a full day for that so don’t try and fit it in unless you can add an extra overnight stop somewhere (we did Williams but Flagstaff also works).

There’s a lot to see in this state from the enormity of the Meteor Crater to small towns with a retro vibe and of course, plenty of roadside quirky stops.

I’ve chosen Kingman for our overnight stop. For an evening meal try Mr D’z or alternatively Rutherford’s 66 Family Diner.

Accommodation option for day 11:

Kingman is home to the El Trovatore Motel which is a classic retro offering with an awesome sign lit up at night. The whole motel has a ‘map’ painted on it which is claimed to be the longest one in the world!

Railways station in Barstow CA

Day 12: Kingman, AZ – Barstow, CA

Miles to drive: 206

We head into our final state today but before enjoying all the Route 66 attractions in California be sure to head up the winding road to Oatman, an old ghost town that’s been revived as a kind of tourist area.

Our day today consists of ghost towns, desert and some interesting relics of the past. Be sure to fill up on gas as you don’t want to get caught short before heading into the wide open desert with not many options to replenish you. That goes for food too I guess!

Some interesting sights are Roy’s Motel & Cafe in Amboy (although it only serves a few refreshments and souvenirs currently), Bagdad Cafe and the Bottle Tree Ranch.

On the other side of the Mojave desert is Barstow, our stop for the day. Barstow is an old railroad town and you can check out a load of old trains and wagons near the Route 66 museum. If you’re in need of food try Roy’s Cafe which was inspired by the original in Amboy – this one at least is open!

Accommodation option for day 12:

Day 13: Barstow, CA – Santa Monica, CA

Miles to drive: 130

Or final day driving on the actual road has arrived. You’ll either be itching for a day off from being in the car or sad that it’s all coming to an end. Possibly both!

You might like to have a lazier morning today and enjoy the town of Barstow before setting off.

It’s a harder days driving today because you’ll be headed in to Los Angeles and dealing with the traffic from that. There are a few sights that you might like to stop at on the way into the city including the original McDonalds in San Bernardino and also another Wigwam Motel that is begging to be photographed.

Santa Monica is, of course, the final destination for Route 66 travelers. The pier is a final swan song to a wonderful (hopefully) trip.

There are many eating options including a few on the pier itself although you’ll likely be paying a premium for the food there and the view of the ocean. But what a view!

Accommodation option for day 13:

Santa Monica and Los Angeles have a huge array of hotels to choose from. You can go for a special hotel to mark the end of an amazing trip or keep the motel trend going. Entirely up to you!

Day 14: Santa Monica/Los Angeles

Miles to drive: 0

Your final day will be dictated by how and when you need to leave the Los Angeles sprawl. You can choose to enjoy the beach, do some sightseeing in Hollywood or explore more of the city. If time is tight then an organized tour or hop on hop off bus could help you to fit more in. Yes they are VERY touristy, but sometimes needs must!

Accommodation option for day 14:

None – you’re done now, if you want to spend more time in LA or Santa Monica you can add some nights to your existing booking.

If you have 13, 15 or 16 days on Route 66:

If you have some extra time for your vacation and road trip then I’d probably keep the basic itinerary the same. What I would do with your extra time is to either add on a day in Chicago and LA so you can explore there. You could also add a night or 2 in Arizona, either in Flagstaff or Williams and spend a day in the Grand Canyon National Park

If you have a day or two less then you might want to end your trip by not staying in Santa Monica and returning home straight away. Alternatively you could save a night by cutting out Santa Fe on Day 8.

Other itineraries to check out:

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Photo of author

Kirsty Bartholomew

Kirsty Bartholomew became obsessed with Route 66 after taking her kids to see Cars at the cinema way back in 2006. She first visited in 2014 and it didn't help the obsession at all. She now writes about the road, the history and hopes to encourage others to visit and keep it alive.

6 thoughts on “Route 66: 14 day road trip itinerary”

  1. 14 days on route 66 is definitely not enough there are so many sites and side trips to experience 21 days might be more realistic if you can spare the time, all in all the trip is a blast no matter how much time you spend,I can’t wait to go again and check out the stops I couldn’t see the first time. Happy Travels !!

    • yes if you can spare the time then longer is definitely better! But not everyone has that luxury. Like you say you can always go back again! Thanks for the comment.


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