Guide a to Route 66 Road Trip: Get Your Kicks: A Modern Adventurer's Guide to Planning the Ultimate Route 66 Road Trip

Tex Dawson

7/20/20257 min read

Route 66 on wall
Route 66 on wall

Guide a to Route 66 Road Trip: Get Your Kicks: A Modern Adventurer's Guide to Planning the Ultimate Route 66 Road Trip

Ah, Route 66. The Mother Road. A ribbon of asphalt weaving through the heart of America, whispering tales of dusty dreams, roadside diners, and boundless freedom. While decommissioned as a federal highway in 1985, its spirit lives on, calling to history buffs, families, solo adventurers, retirees, and road-trippers of all stripes. Whether you're chasing nostalgia or simply a truly unique American experience, planning a modern Route 66 journey is an adventure in itself. And trust us, it's worth every mile.

​Why Route 66 Still Matters: A Crash Course in History

​Before we hit the road, let's acknowledge the "why." Route 66 wasn't just a road; it was a lifeline. Established in 1926, it connected Chicago to Santa Monica, becoming a crucial artery for migration, especially during the Dust Bowl era when families fled west in search of new beginnings. During WWII, it facilitated military convoys, and in the post-war boom, it became the quintessential symbol of American automobile tourism, giving rise to countless motels, diners, and quirky attractions. It was the road that transformed rural towns into vibrant stops and helped shape the American West. It's a testament to ingenuity, perseverance, and the enduring allure of the open road.

​Today, while much of the original alignment is bypassed by interstates, significant portions remain, meticulously preserved by dedicated enthusiasts. This means your modern road trip isn't just about driving; it's about stepping back in time, connecting with a tangible piece of American history.

Your Trip, Your Way: Tailoring Your Route 66 Adventure

One of the beautiful things about Route 66 is its flexibility. You can embark on the full 2,400-mile odyssey from Chicago to Santa Monica (or vice-versa!), or pick a state or two for a shorter, more focused exploration.

Starting Point & Direction:

* Chicago to Santa Monica (East to West): This is the traditional route, often seen as "going west" with the pioneers and Dust Bowl migrants. You'll gain an hour with each time zone you cross, which is a nice bonus!

* Santa Monica to Chicago (West to East): Less common, but perfectly viable. You'll lose time zones, but the excitement of ending in the Windy City is its own reward.

* Pick a Section: Short on time? Focus on states like Oklahoma and Missouri, which boast extensive stretches of preserved Route 66 and a high concentration of classic attractions. Arizona and New Mexico also offer iconic scenery and stops.

Trip Length:

* The Full Monty (2-3+ Weeks): To truly soak it all in, allow at least two to three weeks. This gives you time for detours, leisurely explorations, and unexpected discoveries.

* State-by-State (3-7 Days per State): If you're tackling segments, allocate a few days per state, adjusting for the density of attractions. Kansas, for example, has a very short section (around 13 miles!), while Illinois, Missouri, and Oklahoma have much more to offer.

* Weekend Warrior (1-2 Days): Even a quick overnight trip to a nearby Route 66 town can capture the spirit of the Mother Road.

Budgeting for the Road: Route 66 is largely a budget-to-mid-range traveler's dream.

* Accommodation: Expect motels (often retro and charming!) to range from $70-$150 per night. Booking ahead, especially in popular spots or during peak season, is wise. For the truly budget-conscious, camping or car-sleeping (where permitted and safe!) can drastically cut costs. Look for independent motels that retain that classic Route 66 vibe.

* Food: Diners are your friend! Hearty, affordable, and authentically American. Budget $15-$30 per person per meal for sit-down places. Packing snacks, a cooler, and making some of your own meals will save a bundle.

* Gas: This is your biggest variable. Route 66 is long! Factor in gas costs for over 2,400 miles, plus any detours. A more fuel-efficient car (or a hybrid) will be your best friend.

* Attractions: Many roadside attractions are free or very low cost. Museums typically have admission fees (often under $20). Plan for a souvenir budget – you'll want something to remember the quirkiness!

Hitting the Pavement: Essential Planning Tips

* Get a Map (A Good One!): Modern GPS will often try to push you onto the interstate. Invest in a dedicated Route 66 guide or map that highlights the old alignments. Apps like "Route 66 Navigation" can also be invaluable.

* Flexibility is Key: While a general itinerary is great, be open to detours! The magic of Route 66 often lies in the unexpected discoveries. See a giant something-or-other on the side of the road? Stop!

* Car Prep: Ensure your vehicle is in top condition. Long stretches of road mean reliable tires, good brakes, and no mystery dashboard lights.

* Pack Smart: Comfortable clothes, layers (temperatures vary widely across states), good walking shoes, sun protection, and a first-aid kit are essentials. Don't forget a camera!

* Offline Access: Cell service can be spotty in rural areas. Download maps, music, and any crucial information before you go.

* Embrace the Retro: Stay in vintage motels (many have been lovingly restored!), eat at classic diners, and immerse yourself in the bygone era.

The Best of the Best: Must-See Stops Along the Way (East to West Highlights)

This is just a taste – prepare for countless other gems!

Illinois: The Beginning of the Dream

* Chicago: Start at the official "Begin Route 66" sign on E. Adams Street. Explore Navy Pier, grab a deep-dish pizza, and feel the buzz of the big city.

* Lou Mitchell's Restaurant (Chicago): A legendary breakfast spot where tradition reigns. Men get doughnut holes, ladies get Milk Duds!

* Gemini Giant (Wilmington): One of the iconic "Muffler Men" – a towering fiberglass figure holding a rocket. Perfect for a goofy photo op.

* Abraham Lincoln Presidential Library and Museum (Springfield): A truly impressive museum for history buffs, delving into the life of the 16th president.

* Cozy Dog Drive In (Springfield): Home of the original "Cozy Dog" (corn dog on a stick). A Route 66 culinary institution.

Missouri: The Show-Me State's Charms

* St. Louis: The Gateway Arch is a must-see, symbolizing the westward expansion Route 66 facilitated. Ride to the top for incredible views. Don't miss the National Blues Museum.

* Ted Drewes Frozen Custard (St. Louis): A St. Louis staple since 1929. Deliciously thick frozen custard – prepare for a line!

* Meramec Caverns (Stanton): Explore these extensive underground caves, famously a hideout for Jesse James.

* World's Largest Rocking Chair (Fanning): Because why not? Another fun, giant roadside attraction.

* Route 66 State Park (Eureka): A peaceful stop with exhibits on the Mother Road's history.

Kansas: A Short But Sweet Stretch

* Galena: Though brief, Kansas offers charm. See the "Cars on the Route" (formerly "Four Women on the Route") and the tow truck that inspired "Tow Mater" from the movie Cars.

* Rainbow Arch Bridge (Baxter Springs): A beautiful, historic bridge and one of the last remaining examples of its kind on Route 66.

Oklahoma: The Heart of the Mother Road

* Blue Whale of Catoosa: A quirky, beloved concrete whale structure over a pond. Great for families and picnics.

* POPS (Arcadia): A modern, vibrant stop with hundreds of soda pop flavors and a giant soda bottle sculpture.

* Oklahoma Route 66 Museum (Clinton): Often cited as one of the best Route 66 museums, offering a comprehensive look at the road's history and culture.

* Lucille's Service Station (Hydro): A lovingly preserved historic filling station, a testament to simpler times.

Texas: Big Sky and Quirky Art

* Big Texan Steak Ranch (Amarillo): Famous for its 72oz steak challenge (eat it all in an hour, it's free!). Even if you don't attempt it, the kitschy atmosphere is worth a stop.

* Cadillac Ranch (Amarillo): An iconic art installation of half-buried, graffiti-covered Cadillacs. Bring your own spray paint and leave your mark!

* MidPoint Café (Adrian): Exactly 1,139 miles from Chicago and 1,139 miles from Santa Monica. Try their "Ugly Crust Pie"!

* Glenrio Ghost Town: A fascinating glimpse into a town bypassed by the interstate, now largely abandoned.

New Mexico: Land of Enchantment

* Tucumcari: A town that embraces Route 66, with numerous neon signs and classic motels like the Blue Swallow Motel.

* Santa Rosa Blue Hole: A natural, crystal-clear artesian spring that's popular for diving.

* Albuquerque: Take the historic Central Avenue (old Route 66) through the city. Visit the 66 Diner for a classic experience.

* El Rancho Hotel (Gallup): A grand, historic hotel that housed Hollywood stars during the Golden Age.

Arizona: Canyon Views and Wild West

* Petrified Forest National Park / Painted Desert: A stunning natural wonder where you can see ancient petrified wood and vibrant badlands. Route 66 historically cut right through it.

* Winslow: "Standin' on the Corner" Park: Fans of the Eagles song will love this spot, complete with a flatbed Ford and a mural.

* Grand Canyon (Detour!): While not directly on Route 66, a detour to the Grand Canyon South Rim from Williams or Flagstaff is highly recommended. It's an unforgettable natural marvel.

* Seligman: Considered the "Birthplace of Historic Route 66," this town is full of classic cars, diners (like Delgadillo's Snow Cap Drive-In – prepare for jokes!), and souvenir shops.

* Oatman: A truly unique old mining town where wild burros roam the streets! It feels like stepping onto a movie set.

* Kingman: Arizona Route 66 Museum: Housed in the historic Powerhouse, it's an excellent museum detailing the route's history in Arizona.

California: The End of the Trail

* Roy's Motel & Café (Amboy): A famous, isolated stop in the Mojave Desert with its iconic sign. A popular photography spot.

* Barstow: Harvey House Railroad Depot & Route 66 Museum: A beautiful historic building housing a great museum.

* Wigwam Motel (Rialto/San Bernardino): "Sleep in a Teepee!" One of the last remaining Wigwam Motels in the country.

* Santa Monica Pier: The official "End of the Trail" sign. Enjoy the amusement park, grab some seafood, and watch the sunset over the Pacific Ocean – a fitting end to an epic journey.

Beyond the Asphalt: Tips for Different Travelers

* For History Buffs: Look for the brown "Historic Route 66" signs. Dive into the numerous small town museums. Read "The Grapes of Wrath" or watch "Easy Rider" before you go.

* For Road Trippers: Embrace the detours. Pull over for every interesting sign. Chat with locals – they often have the best hidden gem recommendations.

* For Families: Mix in natural wonders (Grand Canyon, Petrified Forest), quirky roadside attractions (Blue Whale, Cadillac Ranch), and stops with space to run around. Pack games for the car.

* For Solo Travelers: Enjoy the freedom of your own schedule. Many motels and diners are welcoming. Embrace the solitude and reflection the open road offers.

* For Retirees: Consider a slightly slower pace. Pre-book accommodations for peace of mind. Many attractions are accessible. The ideal time to travel is Spring (April-June) or Fall (September-October) for pleasant weather and fewer crowds.

The Humor of the Highway: Expect the Unexpected

Route 66 is rife with oddities, from giant statues to quirky signs. You'll encounter friendly locals, eccentric collectors, and perhaps even a few "characters." Don't be afraid to strike up conversations, ask questions, and embrace the charmingly unpolished nature of many of the stops. The occasional rundown building or unexpected detour is all part of the authentic experience. Remember, it's not about perfection, it's about the journey and the stories you'll collect along the way.

So, fire up your engine, put on your favorite road trip playlist, and prepare to discover why Route 66 isn't just a road—it's an unforgettable

adventure. Get your kicks, because the Mother Road is calling!

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