Route 66 First Half Itinerary: Illinois to Texas

Driving the entire length of Route 66 is a bucket-list road trip, but not everyone has the time to take off work for a long adventure. That’s why breaking up the journey into sections can be a great way to experience the Mother Road without feeling rushed. If you’re working with a couple of weeks of PTO, this Route 66 First Half Itinerary will take you from the highway’s starting point in Chicago, Illinois, to its official midpoint in Adrian, Texas, in 14 days. You’ll have plenty of time to explore classic roadside attractions, historic towns, and iconic diners while making memories along the way.

If you’re looking for other ways to divide up your trip, we’ve got you covered! Check out our 1-week, 2-week, 3-week, and 4-week Route 66 itineraries to find inspiration for a schedule that works for you, or browse our full collection of Route 66 road trip itineraries for more ideas on how to tackle the route at your own pace. And if you haven’t tackled the second half yet, be sure to check out our Second Half of Route 66 guide to help you plan your trip from New Mexico to California. However you decide to break it up, we’ll help you make the most of every mile!

Once you’ve completed this first leg of your journey, don’t stop there! Keep the adventure going by following our Route 66 Second Half Itinerary, which will guide you from New Mexico all the way to California. There’s still plenty of road ahead, and you won’t want to miss what’s waiting on the other side of the Midpoint!

Once you reach Adrian, Texas—home of the famous Midpoint sign and a well-earned slice of pie at the MidPoint Café—you’ll be halfway to the Pacific. But don’t stop there! When you’re ready to continue your journey west, plan the second half of your trip with our Route 66 Second Half Itinerary, guiding you from New Mexico to California and all the way to the Santa Monica Pier.

Why should you split your Route 66 journey in half?

Driving all of Route 66 in one go is an incredible experience, but it’s not always practical. The full journey from Chicago to Santa Monica spans over 2,400 miles, and while it’s possible to complete it in two weeks, or even one, that often means long days of driving with limited time to stop and explore. Splitting your Route 66 adventure into two separate trips—one covering Chicago to Adrian, Texas, and another from New Mexico to California—lets you travel at a more relaxed pace, giving you time to truly enjoy the history, roadside attractions, and hidden gems along the way.

For many travelers, work schedules and PTO (paid time off) are major considerations when planning a Route 66 trip. Not everyone can take a full month off at once, but breaking the journey into two separate trips—each around two weeks long—makes ita much more manageable vacation. By traveling in segments, you can take advantage of long weekends, holidays, or staggered vacation time without feeling rushed. Plus, spacing out the journey allows you to savor each half of the route without worrying about making it all the way to California in a limited timeframe.

Another big advantage of a split Route 66 trip is flexibility. Maybe you want to drive the first half now and save the second half for a future vacation. Or perhaps you want to experience different seasons on the road—catching the fall colors in the Midwest on one leg and the desert landscapes of the Southwest in spring. No matter how you decide to divide your journey, taking it in sections lets you maximize your experience while making the most of your time and budget.

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How to Maximize Your Time and Enjoyment on the First Half of Route 66

Book Your Accommodation Ahead

While you’ll have plenty of time on the road to be flexible, pre-booking your hotels and motels can help ensure a smoother journey. Some of Route 66’s most iconic stays—like the Wagon Wheel Motel or Boots Court—fill up quickly, especially during peak travel seasons. Reserving rooms in advance means you won’t have to worry about last-minute availability and can spend more time enjoying the road.

Consider a One-Way Rental or Return Route Options

If you’re driving the first half of Route 66 as a standalone trip, you’ll need to decide how to get back home. A one-way rental car can be a great option if you plan to fly out of Amarillo or another nearby airport.

Plan for Rest Days

Even though two weeks is a comfortable pace, driving every day can still get tiring. Plan for at least one or two rest days where you stay in a single location and explore at a relaxed pace. Cities like St. Louis and Oklahoma City offer plenty of attractions to fill a full day without getting back behind the wheel.

Stop at Double-Duty Attractions

To maximize your time, look for attractions that serve multiple purposes. Stay at a historic Route 66 motel that also has a museum or gift shop. Grab a meal at a diner that doubles as a roadside attraction. Stop at vintage gas stations that now function as photo-worthy visitor centers. These kinds of places help you see more without cramming your schedule too tight.

Balance Quality and Quantity

With two weeks on the road, you have room to decide whether you want to see as many sights as possible or take your time at select stops. If you love history, you may want to linger at museums like the Route 66 Hall of Fame in Pontiac, Illinois, or the Oklahoma Route 66 Museum in Clinton. If you’re more into unique roadside attractions, plan extra time for spots like the Blue Whale of Catoosa or the Cadillac Ranch near Amarillo. Customizing your itinerary to fit your interests ensures you’ll enjoy every mile.

Be Flexible

Even with a well-planned two-week itinerary, unexpected things will happen. Some attractions might be closed for maintenance, you might discover a local festival you didn’t know about, or you could find a hidden gem that makes you want to adjust your plans. Leaving room for spontaneous detours and discoveries can make your trip even more memorable. After all, the spirit of Route 66 is all about adventure!

Route 66 First Half Road Trip at a Glance

There are infinite ways to split up a Route 66 road trip. This is our recommended breakdown for a two-week Route 66 first-half road trip. Below we will expand this travel itinerary to show all the highlights you’ll see along the way!

Route 66 First Half Itinerary

Now that you’ve decided to take on the first half of Route 66, it’s time to hit the road! This two-week itinerary will guide you from the bustling streets of Chicago, Illinois, to the midpoint of the Mother Road in Adrian, Texas. Along the way, you’ll pass through five of the eight states, stopping at classic roadside attractions, historic diners, and unforgettable landmarks that define the Route 66 experience.

Each day of this itinerary is carefully planned to balance driving time with must-see sights, great food, and unique overnight stays. You’ll explore big cities like St. Louis and Oklahoma City, charming small towns like Pontiac and Atlanta, and quirky roadside stops like the Blue Whale of Catoosa and Cadillac Ranch. Whether you’re fascinated by Route 66 history, love offbeat attractions, or just want to soak in the scenery, this guide ensures you’ll make the most of your journey.

Below, you’ll find a detailed breakdown of what to see, do, eat, and where to stay each day. So, fuel up, set your playlist, and get ready for an unforgettable ride on the first half of Route 66!

Before setting off on your Route 66 adventure, take a day to experience the best of Chicago! This two-week itinerary begins with time to explore the Windy City, giving you a chance to dive into its history, grab a bite of its famous deep-dish pizza, and see some of its top sights before hitting the road.

If you’re flying in, you’ll want to pick up your rental car either at the airport or a location in the city. If you’re staying downtown, keep in mind that parking can be expensive, so be sure to plan ahead. Already driving your own car? That just means you’ll be ready to roll first thing in the morning!

When it comes to accommodations, Chicago has plenty of options, from high-rise hotels to historic inns. But if you want to kick things off with a bit of Route 66 charm, check out our list of classic Route 66 motels in Illinois. No matter where you stay, be sure to rest up—once you hit the road, the adventure really begins.

Of course, you can’t leave Chicago without doing a little sightseeing first! Here are some great ways to make the most of your time in the city before setting off on Route 66:

• Take an architectural boat tour, one of the best ways to see Chicago.
• Explore the Art Institute of Chicago, one of the best museums in town, located right across the street from the Route 66 Begins Sign.
• Have a meal at The Berghoff Restaurant, which opened before Route 66 in 1898.
• See Chicago from above with a trip to the Willis Tower Skydeck.
• Explore the neighborhoods! Chicago is more than downtown. Hop on the el and check out some of the neighborhoods like Lakeview, Wicker Park, or Lincoln Square.
• Try some famous Chicago Deep Dish Pizza at Lou Malnati’s, Pizzeria Uno, or Pizano’s, or on a Chicago Pizza Tour.
• Take in a show at the Chicago Symphony Orchestra, Goodman Theatre, Steppenwolf, or Broadway in Chicago.
• Visit the “official” Route 66 starting point at Navy Pier, marked with a “The Road Begins Here” sign and a mural inside Harry Caray’s Tavern.

Tomorrow, the real adventure begins! You’ll leave behind the towering skyscrapers of Chicago and trade them for neon-lit diners, offbeat roadside attractions, and the historic pavement of Route 66. This is where your journey west truly kicks off, so soak in your time in the Windy City—because from here on out, it’s all about the open road and the magic of the Mother Road!

Your first official day on Route 66 takes you from Chicago to Atlanta, Illinois, kicking off your journey with a mix of classic roadside stops and small-town charm. Start your morning with a must-have photo at the Historic Route 66 Begin Sign before fueling up for the road ahead at Lou Mitchell’s Restaurant. This legendary diner has been serving travelers since 1923, and if you arrive early (they open at 6 or 7am Wednesday through Sunday), you’ll beat the rush and get a head start on your drive.

From here you have a lot of ground to cover and a lot of fun things to see along the way. Here are some potential highlights to add to your day two itinerary:

• It will be too early for lunch, but you can still pull over at Henry’s Drive-In to check out their giant hot dog.
• Meet the Blues Brothers (in statue form) and learn local history at the Joliet Area Historical Museum and Route 66 Welcome Center. While in town, stop at the Rich & Creamy, Route 66 Park, and Dick’s Towing Service.
• Give a space-age hello to the Gemini Giant Muffler Man.
• Explore Ambler’s Texaco Gas Station and take photos with one of the interactive 3D Route 66 Shield Sculptures.
• Step into history at the Odell Historic Standard Oil Filling Station.
• Learn more about Route 66 in Illinois and take your picture in front of one of the biggest murals on The Mother Road at the Illinois Route 66 Hall of Fame and Museum.
• Take a walk down memory lane at Route 66 Memory Lane an original stretch of The Mother Road.
• Pull over to explore Sprague’s Super Service.
• Make a sweet pit stop at Funks Grove Pure Maple Sirup Farm.

Where to Eat Lunch on Route 66 in Illinois

You might pass them a little too early in the day for lunch, but if you can swing it, the fried chicken Dell Rhea’s Chicken Basket in Willowbrook or White Fence Farm in Romeoville can’t be beat.

If you’re not hungry until a little later in the drive, save your appetite for some of Polk-a-Dot Drive In‘s famous chili cheese fries in Braidwood or a down-home bacon cheeseburger at Old Log Cabin in Pontiac.

Browse Illinois Route 66 Restaurants

By the time you reach Atlanta, Illinois—known as the “Land of the Giants“—you’ll be ready for some quirky photo ops. Pose with the hot dog-holding Muffler Man, then head across the street to the American Giants Museum, where you can see the Snerd Giant, Texaco Big Friend, Carpet Viking, Space Man, Indian Brave, and Phillips 66 Cowboy up close. While in town, check out the Atlanta Route 66 Park, the historic Atlanta Public Library & Seth Thomas Clock Tower, and the J.H. Hawes Grain Elevator & Museum. If you arrive later in the day, some spots may be closed, but you can still take in their charm from the outside.

Where to Eat and Stay in Atlanta, Illinois

After covering your first 100 miles of Illinois Route 66, Atlanta is the perfect place to rest up for the journey ahead. Grab dinner and a slice of pie at Country-Aire Restaurant, where you can also snap a photo with their new pie-holding Uniroyal Gal. When it’s time to call it a night, settle in at the Travelodge by Wyndham Route 66 Atlanta (formerly The Trail Inn), a cozy roadside stay just down the road, so you’re refreshed and ready for another day on the Mother Road.

Book an Atlanta, Illinois Hotel

Best Illinois Route 66 Motels

On day three of your half Route 66 adventure, the road from Atlanta to Springfield may be short—just 45 miles—but it’s packed with plenty of roadside fun. This stretch is a treasure trove of quirky sights, so keep your camera ready! Along the way, snap a photo with the World’s Largest Railsplitter Covered Wagon, pay a visit to the Abraham Lincoln Watermelon Monument, spot the offbeat Cow in the Corn Sculpture, and pose with the Big Mel-O-Cream Donut.

Once you roll into Springfield, it’s time to explore the capital of Illinois. Start your morning with a donut (or two) from Mel-O-Cream Donuts—because every good road trip needs a sweet start. Then, dive into the city’s rich history and quirky charm:

Learn about the 16th president by visiting the Abraham Lincoln Presidential Library and Museum, Lincoln Home National Historic Site, and Lincoln’s Tomb at Oak Ridge Cemetery.
Tour the Illinois State Capitol Building, Old State Capitol State Historic Site, and Illinois State Museum.
Explore the stories of historic Black people, businesses, and events along Route 66 at Route History.
Visit Springfield’s quirkiest attractions, like the Lauterbach Giant Muffler Man, the Pink Elephant with Martini, and Ace Sign Museum.
Step back in time at Mahan’s Filling Station or Shea’s Gas Station Museum.
Old-School Entertainment – Catch a movie under the stars at the Route 66 Drive-In Theater.

Where to Eat in Springfield, Illinois

When it comes time for lunch and dinner, there are two must-stop Route 66 restaurants you have to add to your itinerary.

For lunch, stop at a fan favorite Cozy Dog Drive In. Home to the original corn dog, this classic joint is a Route 66 classic.

For dinner, head to Route 66 Motorheads Bar and Grill and grab a delicious bite to eat from their curated menu of American favorites (try a local favorite, the horseshoe!), drink an ice-cold drink from the bar, listen to live music, or explore a treasure trove of Americana memorabilia at their museum. Outside you’ll find the World’s Largest Route 66 Sign being held up by a custom muffler man.

Browse Illinois Route 66 Restaurants

After dinner, experience one of the best after-dark attractions on the route: the Route 66 Experience at the Illinois State Fairgrounds. This immersive exhibit highlights all 421 miles of Illinois Route 66, and after sunset, the neon signs bring it to life.

Kick off the morning by checking out any Springfield sights you may have missed. Then, it’s time to hit the road and continue your journey down The Mother Road.

Just south of Springfield, take a drive on the Original Route 66 Brick Road in Auburn, also known as Brick 66, is a beautifully preserved 1.4-mile stretch of hand-laid bricks dating back to 1931.

Next up: Litchfield, Illinois, a small town packed with Route 66 charm. Start at the Litchfield Museum & Route 66 Welcome Center to brush up on local road history, then take a quick detour to see the Litchfield Carnegie Library Building and snap a photo at the Greetings from Litchfield Mural. Don’t forget to check out the Six on 66 Monument, a tribute to the highway’s lasting legacy.

When it’s time to refuel, you can’t go wrong with The Ariston Cafe. Open since 1924, this historic eatery is one of the oldest restaurants on Route 66, serving up a delicious mix of American, Southern, Italian, and Greek favorites.

With a full stomach and a full tank, continue west toward the Illinois-Missouri border. There are plenty of roadside oddities to keep you entertained along the way!

• Drive to the past at the well-preserved 1926 Soulsby Service Station.
• Visit a menagerie of over-the-top roadside attractions at the Pink Elephant Antique Mall.
• Look up to see the towering World’s Largest Catsup Bottle glistening in the sky.
• Cross the Mississippi from Illinois to Missouri by taking a stroll over the Old Chain of Rocks Bridge.

You’ve made it to St. Louis! If you’re looking for dinner consider ordering a local St. Louis–style pizza! The unique pie has a thin, cracker-like crust and is topped with Provel cheese! You can find it at several local establishments, including a favorite chain, Imo’s Pizza.

Don’t forget dessert! Stop at Ted Drewes for their famous frozen custard!

Where to Stay in St. Louis, Missouri

While there aren’t any specific Route 66 hotels in St. Louis, there are a lot of hotels with a history as long as the road. For a special stay, book a room at a historic downtown hotel with a past, like the St. Louis Union Station Hotel, Drury Plaza Hotel St. Louis at The Arch, or Magnolia Hotel St. Louis.

Book a St. Louis Hotel

Best Missouri Route 66 Motels

After crossing the Mississippi River into Missouri, spend your fifth day soaking in all that St. Louis has to offer. This vibrant city is packed with history, culture, and plenty of Route 66 nostalgia. Whether you’re chasing iconic landmarks, quirky roadside attractions, or legendary eats, there’s no shortage of things to see and do before continuing west on the Mother Road.

• Take a tram ride to the top of the Gateway Arch for a breathtaking view of the city and the Mississippi River—or simply admire it from the ground.
• Explore exhibits that tell the story of St. Louis, including its role in Route 66 history, at the Missouri History Museum.
• Stop by the City Museum, a massive, hands-on playground made from reclaimed materials features slides, tunnels, and surreal art installations.
• Visit the National Museum of Transportation, which showcases one of the largest collections of historic trains, cars, and other vehicles in the country.
• Snap a photo with the World’s Largest Amoco Sign, a giant neon tribute to vintage roadside Americana.
• Sample a cold one and meet the famous Clydesdales on an Anheuser-Busch Brewery Tour.
• If the St. Louis Cardinals are in town, catch a game at Busch Stadium and experience the city’s deep-rooted baseball culture.

Where to Eat in St. Louis, Missouri

known for its unique regional cuisine, so don’t miss the chance to indulge in these local favorites:

• Pappy’s Smokehouse: Famous for its mouthwatering Memphis-style ribs, this barbecue joint is a must-stop for meat lovers.
• Charlie Gitto’s: A classic Italian eatery where you can try toasted ravioli, a crispy, cheese-filled St. Louis specialty.
• Crown Candy Kitchen: This retro soda fountain serves up hearty sandwiches and legendary malt shakes.
• Blueberry Hill: A Delmar Loop institution serving up juicy burgers, vintage memorabilia, and a side of live music history.

Browse Missouri Route 66 Restaurants

After a full day of exploring, grab some shut-eye before hitting the road again—because there’s still plenty of Route 66 adventure waiting for you just beyond St. Louis!

Start your morning in St. Louis with a sweet and simple breakfast at Donut Drive-In. This no-frills bakeshop has been serving up fresh doughnuts since 1953. Grab a coffee and a dozen to-go—you’ll want some fuel before diving into your next big Route 66 adventure.

As you head west, make time for a journey underground at Meramec Caverns, one of Route 66’s most famous natural attractions. This sprawling cave system has been wowing visitors since the 1930s with its towering limestone formations and vibrant mineral deposits. Plus, rumor has it Jesse James once used the caves as a hideout! Take a guided tour to see legendary formations like the Wine Table and the Stage Curtain, and soak in the eerie beauty of this underground wonder.

Back on the road, make your way to Cuba, Missouri, a small town packed with Route 66 history and personality. Make a pit stop at Fanning 66 Outpost, home to the Route 66 Rocker, once the world’s largest rocking chair. Snap a photo with this oversized roadside attraction before heading inside to browse souvenirs, snacks, and Route 66 memorabilia.

When hunger strikes, grab lunch at Rich’s Famous Burgers Weir on 66, a cozy restaurant inside a 1932 filling station serving up delicious comfort food. Then, take a stroll around town to admire Cuba’s famous murals. Known as Route 66 Mural City, Cuba boasts vibrant public art that showcases local history, national figures, and scenes from the golden age of travel.

For dinner, get a true taste of Missouri with hickory-smoked barbecue at Missouri Hick Bar-B-Que. This laid-back joint serves up fall-off-the-bone ribs, juicy brisket, and all the fixings in a rustic, Route 66-themed setting.

Wagon Wheel Motel

After a long day on the road, settle in for the night at the Wagon Wheel Motel, the oldest continuously operating motel on Route 66. With 19 beautifully restored rooms, this vintage motor court captures the spirit of the Mother Road while offering all the comforts of a modern stay. Before calling it a night, snap a photo with the glowing neon sign and relax by the firepit, soaking in the nostalgia of this legendary roadside stop.

Learn More About Wagon Wheel Motel

Best Missouri Route 66 Motels

After checking out of the Wagon Wheel Motel, fuel up for the day with a hearty breakfast at Shelly’s Route 66 Café. Whether you go for a stack of fluffy pancakes, a plate of biscuits and gravy, or a made-to-order omelet, you’ll be ready for another day of adventure on the Mother Road. Today, you’re heading west to Springfield, Missouri—but not without a few quirky, historic, and must-see stops along the way!

• Hillbilly Sign at the former Mule Trading Post: A Route 66 relic, this hand-painted sign is a nod to the roadside advertising heyday.
• Larry Baggett’s Trail of Tears Memorial: A personal tribute to the Cherokee forced to walk the Trail of Tears, created by one man over decades.
• Devil’s Elbow Bridge: A historic steel bridge with scenic views of the Big Piney River, named for the treacherous curve that frustrated early loggers.
• Uranus Fudge Factory and General Store: Where the fudge is delicious, and the jokes never stop. Explore the quirky roadside stop, snap photos, and grab some treats for the road.
• Route 66 Neon Park: a glowing park full of restored vintage Missouri neon signs that once lit up the Mother Road.
• Frog Rock: A local legend, this boulder painted like a frog keeps watch over Waynesville.
• Lebanon Route 66 Museum: A small but well-done museum dedicated to the history of Route 66 in Missouri.
• Munger Moss Motel: While you won’t be staying here tonight, be sure to stop for a photo with its iconic neon sign.
• Missouri Route 66 Welcome Center Rest Area: Need a break? This is one of the best Route 66-themed rest stops on the journey.

You’ve made it to Springfield, Missouri, “The Birthplace of Route 66!” Springfield holds a special place in Route 66 history—this is where the highway officially got its name in 1926! Today, it’s a city packed with historic landmarks, roadside oddities, and plenty of charm. Here are some must-see spots while you’re in town:

• Check out a 35-foot-tall World’s Second Largest Fork.
• Visit the Birthplace of Route 66 Roadside Park, great place to soak in some history and snap a few Route 66-themed photos.
• Take selfies with the Hubcaps on Route 66 Sculpture, creative ode to classic cars and the open road.
• Get insider tips, maps, and Route 66 souvenirs at the Springfield Route 66 Visitor Center.
• Learn all about Springfield’s past, including its Route 66 roots, at the History Museum on the Square.
• Take photos with the Birthplace of Route 66 Monument and explore Birthplace Plaza.
• Seek out the Air and Military Museum of the Ozarks, a hidden gem for aviation and military buffs.
• If you love vintage cars, the Route 66 Car Museum is a must-visit.
• Go underground at the Crystal Cave or Fantastic Caverns for some stunning cave formations and a unique adventure.
• Have fun at Getaway Golf, a Route 66-themed mini-golf course that’s fun for all ages.
• Pull over at Buc-ee’s, a gas station-meets-shopping-experience is a road trip essential.
• Catch a show or admire the beautifully restored Gillioz Theatre from the outside.

Springfield is all about classic Route 66 diners and drive-ins, and today’s menu is all about burgers! Try a classic burger in a retro setting at Joe’s Route 66 Diner in Strafford! Or seek out a chain with a twist: Route 66 Steak ‘n Shake. Want a burger with a twist? Try a burger at Black Sheep Burgers and Shakes or Civil Kitchen. Eat in or grab a burger to go—you might want a late-night snack at your motel!

If you’re looking for a nightcap after a long day on the road, end your night at The Golden Girl Rum Club for a tropical cocktail or Mother’s Brewing Company for a local pint.

Where to Stay in Springfield, Missouri

Springfield has plenty of chain hotels, but for a true Route 66 experience, book a night at one of these classic motels:

• Best Western Route 66 Rail Haven: a historic motor court-turned-modern motel with themed rooms (stay in the Elvis Suite if you can!).
• Rockwood Motor Court: a beautifully restored vintage motel with a cozy, nostalgic vibe.

Book a Springfield Hotel

Best Missouri Route 66 Motels

Start your morning with a classic diner breakfast at College Street Cafe, a Springfield staple serving comfort food since the 1950s. Load up on eggs, toast, and a hot cup of coffee—you’ll need the energy for another day on Route 66!

Use the morning to check off anything you didn’t get to on day seven, but don’t pack your schedule too tight—leave a little room for spontaneous stops between Springfield and Carthage.

While you could spend another night in Springfield, consider getting a head start on tomorrow’s drive by making the one-hour trip to Carthage. Along the way, be sure to check out these must-see Route 66 stops:

• Gary’s Gay Parita: a lovingly restored 1930s-era gas station and one of the most beloved stops on Route 66. Meet the owners, snap photos, and browse the collection of vintage memorabilia.
• Spencer Station: a ghost town-like stretch of Route 66 featuring a restored 1920s filling station and garage.
• Red Oak II: an entire relocated town turned into an open-air museum, created by artist Lowell Davis. Wander past vintage buildings, classic cars, and quirky folk art.
• Precious Moments Chapel: a whimsical and unexpected stop, this chapel is filled with Precious Moments artwork and serene gardens.

You’ve made it to Carthage, home of the Boots Court Motel—one of the most iconic Route 66 motels still in operation.

Boots Court Motel

First opening its doors in 1939, Boots Court is a time capsule of 1930s and 40s roadside lodging. The 13 fully restored rooms feature period-correct art deco headboards, chenille bedspreads, and vintage furnishings, offering travelers a true Route 66 experience.

Be sure to check out the on-site visitor center and gift shop while you’re here!

Learn More About Boots Court Motel

Best Missouri Route 66 Motels

After settling in, take a short drive to Joplin for a mix of Route 66 history and delicious dining options. Stop at Route 66 Mural Park, a perfect photo stop, featuring murals celebrating Joplin’s place on the Mother Road, then grab dinner at one of these local spots:

• Red Onion Café: a cozy, locally loved spot serving steaks, seafood, and pasta.
• Undercliff Grill & Bar: A unique cave-like restaurant built into the side of a bluff.
• Wilder’s Steakhouse: a classic fine-dining steakhouse that’s been around since the 1920s.

After dinner, head back to the Boots Court Motel for a quiet, nostalgic night’s sleep—tomorrow is a big day on Route 66!

Today’s journey is a big one, taking you through three states: Missouri, Kansas, and Oklahoma. Start your morning with a hearty diner breakfast at Iggy’s Diner, a modern joint with retro charm. Whether you go for an egg special, chicken fried steak, or a stack of pancakes, you’ll be fueled up for the road ahead!

Once you’re sufficiently satisfied, hop in your car, and cruise down the last few miles of Missouri and into Kansas.

Kansas has the shortest stretch of Route 66—just 13 miles—but it’s packed with roadside charm. Plan time to stop at these must-see spots:

• Drive under the Route 66 Centennial Arch and through the Drive-Through Route 66 Sign.
• Meet the real-life inspiration for Tow Mater and other cars inspired from Cars at Luigi’s Pit Stop and Cars on the Route.
• Learn about the region’s rich mining history at Galena Mining and Historical Museum.
• Stop at Gearhead Curios, a fun and photogenic Route 66 stop, for souvenirs, photo ops (check out their custom muffler man), and one of the best bathrooms on Route 66.
• Grab souvenirs and a sandwich at Nelson’s Old Riverton Store, 1925 general store.
• Drive or walk across the Rainbow Bridge, the last remaining Marsh Arch Bridge on Route 66.
• Baxter Springs Heritage Center & Museum – Discover Kansas’ Wild West and Route 66 past.
• Pick up Route 66 info and explore a historic gas station at Baxter Springs Independent Oil and Gas Service Station Visitors Center.

After crossing from Kansas into Oklahoma, it’s time to explore even more Mother Road icons. Don’t miss these stops:

• Grab a burger at Waylan’s Ku-Ku Burger, a vintage fast-food joint.
• Drive to Dairy King, a charming roadside stop serving Route 66-shaped cookies, and Allen’s Conoco Fillin’ Station across the street.
• Check out Coleman Theatre, a lavish 1929 vaudeville theatre worth a visit.
• Grab a meal at the longest continually-operated family restaurant in the state, Clanton’s Cafe.
• Stop at Hi-Way Cafe for lunch or just to see Big Bill or the Big Chef, their towering muffler men.
• Explore the world’s largest concrete totem pole and other folk art creations at Ed Galloway’s Totem Pole Park.
• Take photos at the Blue Whale of Catoosa, one of Route 66’s most famous photo ops!

Tulsa is your final destination for the day and where you’ll be staying for two nights. Kick off your stay with Tex-Mex at El Rancho Grande, a Tulsa staple since 1953. After dinner, head to your hotel to rest up for a full day of Tulsa adventures tomorrow!

Where to Stay in Tulsa, Oklahoma

Tulsa offers great hotel options, from historic motels to modern stays. Some top choices include:

• Desert Hills Motel: a classic Route 66 motel with a glowing neon sign.
• The Campbell Hotel: a renovated 1920s landmark with themed rooms.
• Hotel Indigo: a modern boutique hotel with Route 66-inspired decor.

Book a Tulsa Hotel

Best Oklahoma Route 66 Motels

After a week and a half on the road, it’s time to slow things down and enjoy a full day in Tulsa, Oklahoma. This city is bursting with Route 66 history, from vintage neon to quirky roadside attractions, plus a mix of stunning Art Deco architecture, top-notch museums, and scenic spots to stretch your legs.

A full day here lets you explore at your own pace—whether you want to dive deep into Mother Road nostalgia, soak up some local culture, or just enjoy a day off from driving. So park the car, take a deep breath, and get ready for a day of adventure in Tulsa!

There are plenty of things to see, both on Route 66 and off, in Tulsa, making it an ideal place to place roots for a day. Here are some of the best Tulsa Route 66 attractions to include in your day in the city:

• Start your morning right with a hearty breakfast at Wildflower Cafe—a cozy, local favorite with a great menu.
• Stop at Buck Atom’s Cosmic Curios on 66. Shop for fun Route 66 souvenirs and snap a photo with Buck Atom the Space Cowboy Muffler Man and his cosmic companion, Stella Atom the Space Cowgirl Uniroyal Gal.
• Make your way to the Meadow Gold Sign, a restored Route 66 icon. While you’re there, pop into Meadow Gold Mack’s and 66 Collective for a little shopping and visit the Meadow Gold Mack Muffler Man, Cowboy Bob Muffler Man, and Rosie the Riveter Uniroyal Gal.
• Pay a visit to the East Meets West Symbolic Route 66 Midpoint sculpture, then take a stroll through Tulsa’s Neon Park, where glowing signs light up the city’s rich history.
• Learn powerful stories at the Greenwood Cultural Center and Black Wall Street Memorial, an essential stop to reflect on Tulsa’s history and resilience.
• Stand next to The Golden Driller, one of the tallest freestanding statues in the U.S., towering over the Tulsa Expo Center.
• Step back in time at the Route 66 Historical Village, an open-air museum showcasing a restored gas station, steam engine, and more.
• If you’re a fan of classic films, visit The Outsiders House Museum, where you can walk through the set of the iconic 1983 movie.
• Music lovers have a big choice to make—explore the legacy of folk legend Woody Guthrie at the Woodie Guthrie Center or dive into the world of Bob Dylan at the Bob Dylan Center.
• For a bit of fresh air, wander through The Gathering Place, one of the best urban parks in the country.
• End your day by catching a show (or just admiring the neon sign) at Cain’s Ballroom, a legendary venue that has hosted everyone from Bob Wills to The Sex Pistols.
• If you’re up for a little side trip, take a short drive to Sapulpa and wrap up the night with a drive-in movie at the Tee-Pee Drive-In—a classic way to end a day on Route 66!

Where to Eat Lunch and Dinner in Tulsa

Hungry? Tulsa has no shortage of great eats! For a classic diner experience, Tally’s Good Food Café serves up big portions of homestyle comfort food in a retro setting. If you’re in the mood for variety, check out Mother Road Market, a modern food hall with something for everyone.

Browse Oklahoma Route 66 Restaurants

After a full day of Tulsa exploration, rest up—because there’s still plenty of Route 66 ahead!

Get ready for another exciting day on Route 66 as you make your way from Tulsa to Oklahoma City! This stretch of The Mother Road is packed with quirky roadside oddities, historic landmarks, and unforgettable stops. After checking out of your Tulsa hotel, hit the road and keep that camera ready—you never know what fun sights you’ll come across!

• Snap a photo at the Crossroads of America Sign, a fun Route 66 marker celebrating the Mother Road’s legendary path.
• Fuel up on nostalgia at the Heart of Route 66 Auto Museum, home to classic cars and the World’s Tallest Gas Pump.
• Swing by the Bristow Train Depot and Museum to explore a piece of Oklahoma’s railroad history.
• When hunger strikes, Rock Cafe in Stroud is the perfect pit stop. This Route 66 icon has been serving travelers since 1939—and its history even inspired the character of Sally in Cars!
• While in Stroud, pull over at the Neon on Main neon signs, including the famous sign at Skyliner Motel.
• Take a drive over history itself on Brick Paved Broadway Street, a preserved stretch of original Route 66 pavement in Davenport.
• In Chandler, dive into the past and future of Route 66 at the Chandler Route 66 Interpretive Center, where interactive exhibits bring the highway’s history to life.
• Even if you don’t have time for a game, stop at Rt 66 Bowl in Chandler just to admire its vintage neon sign!
• Drive by the Historic Threatt Filling Station, a former Black-owned service station that played a significant role in Oklahoma’s history.
• Check out OK County 66, a quirky roadside attraction filled with miniature versions of famous Route 66 landmarks—it’s like a tiny road trip within your road trip!
• Stretch your legs at the Arcadia Round Barn, an architectural gem that has stood along Route 66 since 1898.
• When it’s time for a refreshing break, stop at Pops 66 in Arcadia. With hundreds of different soda flavors and the World’s Largest Soda Bottle out front, it’s a true Mother Road must-visit.
• Before reaching Oklahoma City, make a quick detour in Edmond to snap a fun photo with the Blue Hippo, one of Route 66’s quirkiest mascots.

After a full day of exploring, settle into your Oklahoma City hotel and refuel at one of the city’s top restaurants: Cattlemen’s Steakhouse, Cheever’s Cafe, or Leo’s BBQ.

Where to Stay in Oklahoma City, Oklahoma

Oklahoma City offers plenty of great places to stay, but if you’re looking for something unique and vintage-chic, check out The Classen Inn. This renovated 1963 motel blends retro Googie architecture with modern amenities and bold, Instagram-worthy artwork.

Book two nights because tomorrow is all about exploring Oklahoma City’s Route 66 treasures!

Book an Oklahoma City Hotel

Best Oklahoma Route 66 Motels

Oklahoma City offers a vibrant mix of history, culture, and roadside charm, making it the perfect place to spend a full day exploring. Whether you’re tracking down Route 66 landmarks, diving into the city’s Western heritage, or just looking for some great food, OKC has something for every traveler. And today is all about discovering what makes this city special! Here are some of the must-do things in Oklahoma City to add to your travel itinerary:

• Find the Milk Bottle Grocery, a tiny triangular building topped with a giant milk bottle.
• Admire the Gold Dome Building, a stunning example of Mid-Century Modern architecture, and check out the Oklahoma State Capitol, the only U.S. state capitol with working oil wells on its grounds.
• Catch a show (or just admire the neon) at the historic Tower Theatre, one of OKC’s best-loved music and event venues.
• Take a spin on the Wheeler Ferris Wheel, originally from the Santa Monica Pier, and snap a photo with the Giant OKC sign.
• Eat, shop, and explore street art in Bricktown, a lively entertainment district filled with restaurants, bars, and local charm.
• Get a taste of cowboy culture at the National Cowboy & Western Heritage Museum, home to incredible Western art and artifacts.
• Visit one of Oklahoma City’s quirky museums—whether it’s the American Banjo Museum, the Oklahoma Museum of Telephone History, or the American Pigeon Museum & Library, there’s a little something for everyone!
• Learn about the history and cultures of Oklahoma’s tribal nations at the First Americans Museum, an essential stop for understanding the state’s Indigenous heritage.
• Spot some modern Route 66 landmarks, like the Route 66 Centennial Sign or the quirky Robots on 66 (RT-19).
• Celebrate local legends by stopping by the Mickey Mantle Statue in Bricktown and the Miss America Statues, which honor Oklahoma’s pageant winners.
• Get lost in an immersive art experience at Factory Obscura, a mind-bending, interactive art collective that feels like stepping into another dimension.
• Reflect at the Oklahoma City National Memorial & Museum, a powerful tribute to the victims and survivors of the 1995 Oklahoma City bombing.

Today is a big travel day as you say goodbye to Oklahoma and roll into Texas. Start your morning with a hearty breakfast at HunnyBunny Biscuit Co. (for biscuits smothered in deliciousness) or Sunnyside Diner (for classic diner favorites). You’ll need the fuel because today is packed with must-see stops!

After filling up on a good breakfast, hop in your car and get ready to explore the rest of Oklahoma! Here’s what you’ll pass on this next leg of your journey.

• Snap some fun photos at the El Reno Mother Road Monument.
• Visit the Muffler Men Cutouts Mural, a unique take on classic Muffler Men.
• Pay your respects to Lucille Hammons, the “Mother of the Mother Road,” who ran Lucille’s Historic Highway Gas Station for decades.
• Have a blast at the Weatherford Rt. 66 Spaceman.
• Dive into the history of The Mother Road, complete with vintage cars, neon signs, and nostalgic exhibits, at the Oklahoma Route 66 Museum.
• Stop at the National Route 66 & Transportation Museum, another must-see museum showcasing Route 66 memorabilia and historic transportation displays.
• Stop in Sandhills Curiosity Shop for a quirky roadside experience, known for its eclectic decor and impromptu musical performances.
• Explore the Ghost Town of Texola, a near-abandoned town on the Oklahoma-Texas border.

Lunch in Oklahoma

If it’s not too early in the day, pull over in El Reno to try a local delicacy: the fried onion burger. With a a caramelized crust of onions fused with juicy beef that’s full of flavor in every bite, this is no ordinary hamburger. Try one for yourself at Johnnie’s Hamburgers & Coneys, Sid’s Diner, or Robert’s Grill.

If you’re not quite hungry yet, save your appetite for Lucille’s Roadhouse in Weatherford, a highway diner built to resemble the original Lucille’s Historic Highway Gas Station.

Browse Oklahoma Route 66 Restaurants

Next up: The Lone Star State! This stretch of Route 66 is full of nostalgic sights, historic landmarks, and quirky roadside stops. Tonight, you’ll stay in Shamrock, Texas, so don’t forget to check out these must-see Shamrock attractions before calling it a night.

• Visit one of the most famous Route 66 landmarks: Conoco Tower Station & U-Drop Inn. this Art Deco gas station and café is a photographer’s dream.
• Learn about Shamrock’s history and see exhibits on ranching, Native American culture, and Route 66 heritage at the Pioneer West Museum.
• Step back in time at the beautifully restored Magnolia Gas Station.
• Kiss the Blarney Stone (or at least a piece of it) at Blarney Stone Plaza or visit the Fake Blarney Stone down the block.

Before retiring to your motel room for the night, treat yourself to dinner at Grif’s Steakhouse, with a menu featuring steakhouse fare like rib eyes, filets, loaded baked potatoes, and bacon-wrapped asparagus. Or stop at the iconic U Drop Inn Cafe for a slice of meatloaf or a pulled pork salad.

Where to Stay in Shamrock, Texas

Shamrock, Texas is a great place to spend the night on your Route 66 road trip. It’s a convenient stopping point for those with lots of attractions on their itinerary. Luckily, Shamrock has plenty of classic motels to choose from, like the Shamrock Country Inn Motel, Western Motel, and Blarney Inn. Book a room and spend some time exploring all the attractions in town.

Book a Shamrock Motel

Best Texas Route 66 Motels

You’ve made it to Day 14 of your Route 66 journey, and today marks a major milestone—it’s the day you reach the official halfway point of the Mother Road…and the end of your journey on the first half of Route 66! From Shamrock to Adrian, Texas, this stretch is packed with wide-open plains, quirky roadside stops, and historic landmarks. After celebrating your Route 66 achievement, you’ll head back to Amarillo for one final night on the road before making your way home.

If you stayed at the Shamrock Country Inn, fuel up with a Texas-shaped waffle before hitting the road! Then, point your wheels west and watch for some must-see Route 66 attractions along the way:

• Stop at 66 Super Service Station, a beautifully restored 1930s gas station.
• Explore the Route 66 Museum & Devil’s Rope Museum, a double-feature of roadside history, covering both Route 66 and the surprisingly fascinating world of barbed wire.
• Check out the Leaning Tower of Texas, a gravity-defying water tower, and Groom Cross, a towering 190-foot cross that dominates the skyline.
• Visit Stoner Patriot Peace Garden of All Faiths, a quiet roadside tribute.

From here you’ve reached Amarillo, Texas! But let’s come back. After all, it is the last day of our halfway road trip and we want to see the halfway point! So it is time to head to Adrian, Texas —the exact middle of Route 66! You’ve officially driven 1,139 miles from Chicago, with 1,139 miles left to reach Santa Monica. Celebrate the moment with:

• A photo at the Route 66 Midpoint Sign, proof that you made it halfway!
• Lunch and a slice of Ugly Crust Pie at the Midpoint Café, a well-earned treat for your travels.
• A souvenir stop at Dream Maker Station to pick up some Route 66 memorabilia to mark the occasion.

With the midpoint checked off, it’s time to double back to Amarillo and close out your trip in style. Explore some quirky sites on your way back then spend the rest of the day exploring the Amarillo’s Route 66 Historic District, a lively stretch of 6th Avenue packed with antique shops, art galleries, and classic Route 66 vibes. Some must-see stops include:

• Cadillac Ranch: bring a can of spray paint and leave your mark on this iconic roadside art installation.
• 2nd Amendment Cowboy Muffler Man: a towering cowboy keeping watch over the road.
• VW Slug Bug Ranch: a smaller, funkier take on Cadillac Ranch, featuring half-buried, graffiti-covered VW Beetles.
• The Giant Legs of Amarillo: a pair of giant, disembodied legs standing mysteriously in the middle of nowhere.
• Floating Mesa: an optical illusion that makes a mesa appear to hover above the horizon.
• Jack Sisemore RV Museum: a nostalgic collection of vintage campers and trailers.

The Big Texan Steak Ranch

After a full day of exploring, cap off your trip with a classic Route 66 meal at The Big Texan Steak Ranch. Whether you take on the famous 72-ounce steak challenge or stick to a more manageable portion, it’s the perfect way to end your adventure.

Learn More About The Big Texan Steak Ranch

Browse Texas Route 66 Restaurants

Where to Stay in Amarillo, Texas

When it comes to finding a place to stay in Amarillo, you’ve got some great options. For a comfortable and affordable stay, Atrea Inn offers modern amenities with a cozy, boutique feel. If you’re looking for a more upscale experience, The Barfield, Autograph Collection blends luxury with a touch of Amarillo’s Western heritage, right in the heart of downtown. And for those who want a classic Route 66 experience, The Big Texan Motel—connected to the legendary Big Texan Steak Ranch—is a fun, themed stay with Wild West-style rooms and easy access to that famous 72-ounce steak challenge.

Book an Amarillo Motel

Best Texas Route 66 Motels

Tomorrow, you’ll start the journey back home, reflecting on two unforgettable weeks on the Mother Road. But this isn’t the end—just a pause. The second half of Route 66, from Texas to California, is still waiting, and it won’t be long before you’re back on the road, ready to complete the adventure.