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Route 66 Road Trip Planner & Guide

Route 66 Road Trip Planner & Guide

U.S. Route 66 has many names–Will Rogers Highway, the Mother Road, Main Street of America–but no matter what name you know it by, Route 66 is the finest living example of classic Americana today, and the passage affords those who travel its distance many unique insights into past American cultures; cultures that are largely forgotten in the world today. From the Dust Bowl migrants hoping to find prosperity in California during the 1930’s, to the few remaining examples of Googie Architecture whose neon signs, and Jetsons-esque structures were once ubiquitous along the historic highway, a Route 66 road trip allows you to take a journey through some of America’s most formative cultural history, with stops at the most breathtaking natural wonders in the world. Check out our Route 66 road trip planner and guide below for a detailed itinerary with stops along some of the Mother Road’s most notable attractions.

Long since bypassed by the interstate system, Route 66 remains in spirit, and at its best,  a rare glimpse into American history, when road trips were romanticized and the open road was your ticket to freedom.

Route 66 Cross Country Road Trip Planner

Route 66 Road Trip Planner - Cross Country Road Trip Planner

Historic Route 66: 2,451 miles of classic Americana, crossing through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.

Route 66 Road Trip Planner & Guide - Midwest    Route 66 Road Trip Planner & Guide - Southwest     Route 66 Road Trip Planner & Guide - West Coast

select a region above to navigate to each section


State Distance Traveled State Distance Traveled
Illinois 301 miles Texas 186 miles
Missouri 317 miles New Mexico 487 miles
Kansas 13 miles Arizona 401 miles
Oklahoma 432 miles California 314 miles
Total Distance Covered: 2451 miles / 8 States

Route 66 Road Trip Planner: What to Bring

Universal Packing List                    GPS & MiFi Rentals from Auto Europe                    The Ultimate Road Trip Playlist

Route 66 Road Trip Guide: Midwest

Route 66 Road Trip Planner & Guide - MidwestWhen starting a Route 66 road trip from Chicago, a number of incredible attractions await you, from the summit of the Willis Tower, to the many nostalgia-inducing cafes and roadside diners that pepper the route as it heads south-west. As you depart Chicago, headed south, be sure to stop by Cozy Dogs in Springfield, Illinois, a widely renowned Drive-In joint that is sure to not only satiate you taste-buds, but also put you in the classic Americana spirit of Route 66. Further south, be sure to stop by the Meramac Caves–400 million year old caves, later used as shelter by Native Americans, and eventually as a saltpeter mine by Union troops during the Civil War. As your journey through the Midwest comes to a close, a stop by the Route 66 Museum in Clinton, Oklahoma is an absolute must. Stock up on memorabilia and souvenirs from the first leg of your road trip journey, before you change direction and head into the harsh desert climate of the American Southwest.

Check out the list below for other great attractions and landmarks along Route 66 in the Midwest.

Notable Route 66 Attractions, Midwest:

Route 66 Road Trip Planner - Grant Park, Chicago, Illinois

Grant Park – Chicago, IL

Route 66 Road Trip Planner - Gateway Arch, St. Louis, Missouri

Gateway Arch – St. Louis, MO

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Route 66 Road Trip Guide: Southwest

Route 66 Road Trip Planner & Guide - SouthwestNow that you’ve escaped the rolling hills and endless flats of the Midwest on your Route 66 Road Trip, next you’ll enter into the iconic American Southwest. Once famous for its contribution to the frontier mystique, many elements of this regions storied past have been maintained for their historic value, and Route 66 offers travelers the most comprehensive glimpse into the unique culture, history, and natural landmarks of the American Southwest. The second leg of your journey begins as you pass through the panhandle of Texas and, and despite being a commonly overlooked part of the state, savvy travelers know that the Texas panhandle is brimming with exploratory potential and one-of-a-kind, breathtaking landscapes. About 30 miles south of Amarillo, Texas, sits the 800ft. deep, 120-mile long, Palo Duro Canyon; your very own miniature Grand Canyon, without the swaths of tourists! Further along Route 66, just outside Flagstaff, Arizona and the Grand Canyon, you will find Meteor Crater, a 50,000 year old meteorite crater that’s nearly a mile wide in diameter. Rarely are we afforded an opportunity to explore natural landmarks of such epic proportions, so be sure stop off at Meteor Crater, at least to admire the immense scale and ancient history of the site.

Of course there are a number of other awesome destinations along Route 66 in the Southwest, so check out the list below for a more detailed guide to the best attractions along your Route 66 Road Trip.

Notable Route 66 Attractions, Southwest:

Route 66 Road Trip Planner - Petrified Forest, Holbrook, Arizona

Petrified Forest – Holbrook, AZ

Route 66 Road Trip Planner - Meteor Crater - Flagstaff, Arizona

Meteor Crater – Flagstaff, AZ

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Route 66 Road Trip Guide: West Coast

Route 66 Road Trip Planner & Guide - West CoastYou’ve nearly made it to Los Angeles, the western-most terminus of historic Route 66. So far you’ve passed through a variety of attractions in the Midwest and Southwest, but the fun doesn’t cease there. As you enter California and continue on towards the Pacific Ocean, myriad incredible Route 66 road trip stops await you. First stop, Roy’s Motel and Cafe, an immaculately preserved example of Googie architecture, and an absolute Route 66 Road Trip staple. Roy’s has been a Route 66 landmark since its inception in 1938 as a roadside gas station, and eventual transformation into cafe, auto repair shop, and motel. Take a bite of  classic Americana at the newly re-opened Roy’s Cafe, and admire it’s famous boomerang shaped sign, before departing on the road towards LA. As you approach the outer limits of the sprawling LA metropolis, stop by two famous Route 66 landmarks, Elmer’s Bottle Tree Ranch, and the California Route 66 Museum; both provide excellent insight into the road trip epoch that took the historic highway by storm. Once within the limits of Los Angeles, a number of exciting attractions await you, from the classic Dodger’s Stadium, to the Santa Monica Pier.

Check out the list below for more Route 66 road trip attractions on the West Coast.

Notable Route 66 Attractions, West Coast:

Route 66 Road Trip Planner - Colorado St. Bridge - Pasadena, California

Colorado St. Bridge – Pasadena, California

Route 66 Road Trip Planner - Chinatown - Los Angeles, California

Chinatown – Los Angeles, California

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Begin your Route 66 Road Trip with Auto Europe

No matter what your travel interests are–architecture, history, cultural exploration, culinary highlights, or unabated relaxation–a Route 66 Road Trip accomplishes it all. No better route exists for experiencing classic Americana than Route 66, from the quaint neon-lit diners and wacky museums, to the awe-inspiring natural landmarks like the Grand Canyon and Meteor Crater, we hope our Route 66 Road Trip Planner with stops guides you through a once-in-a-lifetime vacation experience.

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