A journey of discovery and nostalgia on legendary Route 66 is the quintessential American road trip. It is a journey through the heartland and through time. It is a grand adventure without equal.
So, how do you plan a trip of this magnitude? Time is limited so how do you ensure that on the drive from Chicago to Santa Monica not a moment is wasted? How do you get the most smiles per mile on this epic odyssey?
It starts with two simple tools. The Route 66 Navigation app and the EZ 66 Guide For Travelers by Jerry McClanahan work in a hand in glove manner. These will be your foundation for planning the ultimate road trip. And they will be your copilot and guide while on the road.
These two resources provide detailed maps, turn-by-turn directions, trivia, event information, and information on must-see attractions. They also provide insider tips as well as access to current information about road conditions and closures.
A Journey of Discovery
For the uninitiated or novice traveler, a journey of discovery on iconic Route 66 will spark a lifelong passion for road trip adventure. And in my humble opinion the road trip, any road trip, even a bad road trip, is better than the best day doing anything else.
The very mention of a Route 66 road trip conjures up images of tail fins, smile inducing roadside attractions, neon lit nights, time capsule diners, and the open road stretching across panoramic landscapes. In the era of the renaissance Route 66 evolved into something magical.
The first time Route 66 adventurer often starts by planning a two-week journey along the Main Street of America. So, let me start by saying the two weeks isn’t going to be enough time to truly experience Route 66. Two years might not be enough time.
So, before packing up the suitcases and gassing up the car I suggest selecting a few must-see landmarks. And you might want to create a list of diners, restaurants, and motels that capture the essence of the Route 66 experience. Then fill in the blanks.
Planning Your Route 66 Adventure
Put simply, plan but don’t over plan. You can’t see all the attractions or try all the recommended restaurants in a mere two weeks.
When asked how long it takes to see all that Route 66 has to offer, my answer is simple. I don’t know. After all, I have only been exploring this storied old highway since 1959!
So, a journey of discovery on Route 66 begins with the creation of a game plan. But make sure that that plan isn’t too rigid. Factor in a bit of time for flexibility. Remember, it is more important to take time to talk with people along the way than to try and stick to a schedule. After all, the people are the magic of a Route 66 experience.
And during your odyssey make notes of what you want to see on the next Route 66 adventure. You will be back!
Other Recommendations
This shouldn’t come as a surprise, but I recommend Jim Hinckley’s America when planning a Route 66 odyssey. Our multifaceted network that includes social media, website, books by Jim Hinckley, and Coffee With Jim, the weekly podcast with fascinating guests, is chock full of inspiring road trip ideas.
Attesting to its value for the Route 66 enthusiast, Coffee With, has been officially recognized as a Route 66 centennial program. Podcast guests include business owners, authors, tour company owners, CVB directors, artists, film producers, photographers, historians, tourism and museum directors, and event organizers.
Landmark and Attraction Suggestions
If I were to list every one of my favorite attractions, this would be a very lengthy blog. Besides, half the fun on a Route 66 adventure are the unexpected gems found along the way. This is a journey of discovery!
So, instead of transforming this blog post into a book, I will share a few teasers.
Start in Chicago
Begin your journey in the Windy City, where you can visit the Art Institute of Chicago, Millennium Park, and the Willis Tower before embarking on Route 66. Don’t forget to take a selfie at the Route 66 Begin sign on Adams Street, and have breakfast at Lou Mitchells. For dinner, I suggest a gem that opened its doors in 1898, the Berghoff.
Springfield, Illinois
As you make your way through Illinois, plan to spend some time in Springfield. First, there is the Abraham Lincoln Presidential Library and Museum, Lincoln’s Home and Tomb, and the Old State Capitol. And the Route 66 Experience at the state fairgrounds is a must see attraction.
Time capsules that blur the line between past and present abound along Route 66. In Springfield one of these is the wonderful Cozy Dog Drive-In, home of the original corn dog.
Pontiac, Illinois
Pontiac, Illinois is more than a stop. It is a destination. In this charming village that centers on a stunning mid-19th century courthouse, you will find a treasure trove of attractions that celebrate the history of Route 66 and small-town America.
Pontiac is a living Norman Rockwell painting with a swirl of colorful public art, and lots of Route 66 landmarks. Did you know that there is a monument that was dedicated by President Theodore Roosevelt on courthouse square? Did you know that even alleys in the historic business district are festooned with murals?
Counted among the highlights are the Route 66 Association Hall of Fame and Museum, the Livingston County War Museum, and the Pontiac-Oakland Automobile Museum. For a unique experience, the various outdoor murals scattered throughout the town make for perfect Instagram captures.
While in Pontiac, make a stop at the Old Log Cabin Inn. Nearly a century old this historic restaurant is known worldwide for its hearty traditional American fare. And before I forget, the historic swinging bridges over the Vermilion River, and depending on the weather, a picnic in the park is also recommended.
St. Louis, Missouri
Cross the Mississippi River into St. Louis, home to the Gateway Arch, the historic Anheuser-Busch Brewery, and the Missouri History Museum in historic Forest Park. The Ted Drewes Frozen Custard stand is a Route 66 tradition that shouldn’t be missed.
Often overlooked is Forest Park on the original alignment of Route 66. This historic urban oasis that was the site of a World’s Fair is home to the city zoo and art museum, and other attractions. The National Museum of Transportation, another highly recommended stop, is just west of the city in Kirkwood.
Don’t rush a St. Louis visit. And don’t be deterred by traffic congestion or horror stories of crime. Just use common sense. And do a bit of planning.
Kingman, Arizona
Jumping ahead about 1,500 miles, when you reach Kingman, Arizona, the Route 66 Museum, the Bonelli House, Mohave Museum of History and Arts, and the Locomotive Park are highlights. But to really experience the historic heart of Kingman, consider the QR code based self-guided walking tour narrated by Jim Hinckley. A wide array of historic information, a blog, a planning guide with a listing of restaurants and attractions, and an event calendar are on the website (kingman.tours).
Historic sites, filming locations for famous movies, sites associated with celebrity history, and public art are included in the tour. Along the way there is an eclectic array of shops, photo ops, microbreweries, wine bars, and a diverse array of restaurants.
California and Santa Monica
As you approach the west end of Route 66, the sights and sounds of California beckon. Take time for a tour of the El Garces depot and hotel in Needles. Explore the Mojave Desert Heritage and Cultural Association complex in Goffs. Visit the whimsical Elmer’s Bottle Tree Ranch. Stop at the Wigwam Motel in San Bernardino.
Traffic is the excuse (somewhat valid) that most travelers use to justify a speedy trip through megapolis on the freeway. Don’t do this, after all traffic congestion in the LA area has been a subject of complaint since at least WWII.
The historic theatre district in downtown Los Angeles is one example of what you will miss by taking to the freeway. The original western terminus of Route 66 is located there, and so is the incredible Grand Central Market that opened in 1917.
Then follow Route 66 through Hollywood and Beverly Hills. Finally, end your journey at the Santa Monica Pier, mere blocks from the western terminus.
Travel Tips
- Plan Your Stops Based On Available Time: Research and plan stops. But don’t be myopic and focus on the end of the trip. Be flexible.
- Stay in Unique Motels: Stay at classic motels like Roadrunner Lodge Motel in Tucumcari, New Mexico (ask David for a tiki room), and the Wagon Wheel Motel in Cuba, Missouri.
- Enjoy Local Cuisine: Savor the flavors of Route 66 by dining at local diners and drive-ins. Don’t miss a slice of pie at the MidPoint Café in Adrian, Texas, or the huevos rancheros at Earl’s in Gallup, New Mexico.
- Visit Museums: Explore the numerous museums along the route, such as the Route 66 Association Hall of Fame and Museum in Pontiac, Illinois, and the Oklahoma Route 66 Museum in Clinton.
- Attending Events: Check local event calendars for festivals, car shows, and other special events along Route 66. The Route 66 Fun Run in Kingman, Coors Rodeo in Amarillo, and Czech cultural festival in Yukon, Oklahoma are particularly noteworthy.
Jim Hinckley Recommended Motels and Restaurants
Motels
- Carlinvilla Motel, Carlinville, Illinois
- Country Hearth Inn & Suites, Edwardsville, Illinois
- Wagon Wheel Motel, Cuba, Missouri
- Campbell Hotel, Tulsa, Oklahoma
- Desert Hills Motel, Tulsa, Oklahoma
- Western Motel, Shamrock, Texas
- Blue Swallow Motel, Tucumcari, New Mexico
- El Rancho, Gallup, New Mexico
- Earl’s Motor Court, Winslow, Arizona
- Americana Motor Hotel, Flagstaff, Arizona
- Wigwam Motel, Rialto, California
- Saga Motor Hotel, Pasadena, California
Restaurants
- Cozy Dog Drive-In – Springfield, Illinois
- Old Log Cabin Inn – Pontiac, Illinois
- Ariston Café – Litchfield, Illinois
- Twisted Biscuit – Edwardsville, Illinois
- Weir on 66 – Cuba, Missouri
- Ted Drewes Frozen Custard – St. Louis, Missouri
- MidPoint Café – Adrian, Texas
- Rock Café – Stroud, Oklahoma
Road Trip
A road trip on Route 66 is your personal journey of discovery and nostalgia. It’s an exploration of the American experience.
With some careful planning, using a few inspirational sources, the right resources, and a spirit of adventure, you’ll create memories that last a lifetime. So, pack your bags. Fuel up and get ready to hit the road on the Main Street of America.
Safe travels! And if you need more tips, inspiration, or have questions, Jim Hinckley’s America is your portal to the ultimate American road trip.
Thank you. Shared adventures are the best adventures.