Route 66: Epic Road Trip Start to Finish

Original Historic Route 66 roadway in the Mojave Desert with Route 66 shield painted on the road

U.S. Route 66 is the ultimate epic road trip, a legendary adventure from start to finish across eight states.

Since opening in 1926, Route 66 has been memorialized in books. Hit songs. A TV series. And films, including Pixar’s animated blockbuster Cars.

Join us on a journey unlike any other, an ultimate adventure along the Main Street of America.

Explore, experience, be inspired with us from start to finish on The Mother Road.

Ready? Let’s go!

Route 66: Planning and Perspective

Approach: Old School All the Way

Like travelers of bygone days, our itinerary specifically outlined four parameters:

Firstly, no GPS. Paper maps only.

Secondly, no tech during the day. Phones and laptops out of sight until after we checked into lodging for the night.

Thirdly, indie only. Minimal mod cons. Motels, eateries, attractions, mom-and-pop shops.

Fourthly, no digital photography. Paul shot everything on film.

Jalopy: Caddy Daddy

Brand new, fully loaded, gleaming white Cadillac conveyed us in luxury and style.

The odometer read six miles when Paul and I picked the Caddy up in downtown Chicago, Illinois.

Ultimately the odometer clicked well over 3,000 miles at drop-off in our final destination, San Francisco, California.

Itinerary: East to West

The traditional experience flows east to west:

  • Beginning officially in downtown Chicago, Illinois.
  • Continuing west through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona.
  • Ending officially at the Santa Monica Pier in California.

For seasonal timing, Spring and Fall are typically temperate and pleasant, generally speaking, through all eight states.

We planned our drive for late September through early October.

Our own Route 66 itinerary, start to finish, took 2.5 weeks.

However, you may drive either direction and along any section as you choose.

Experience: Real, Genuine, Authentic

Sincere smiles and friendly hellos greeted us at motels, diners, attractions, mom-and-pop shops wherever we went.

Such warm-hearted welcomes extended to our one unexpected detour from Route 66. We share this unplanned location in the following itinerary.

Our Why: What It’s Really About

We certainly did, of course, get our kicks on Route 66.

Yet as we always say, the WHY underscores everything. So here’s ours:

We wanted to get to the true heart of Route 66, start to finish.

With this purpose in mind:  To understand not only the content but also the context and subtext of this legendary road. Past, present, and future.

In other words: What Route 66 is really about.

Route 66: Top Stops and Timely Tips

Colorful restorations, roadside attractions, and iconic signs enliven the environment everywhere along the route.

So let’s highlight some top stops and get hip to timely tips across Route 66 start to finish.

From the Start

Chicago, Illinois, is the official eastern terminus of Route 66.

Fuel up at Lou Mitchell’s (565 West Jackson Boulevard, Chicago). Since 1923, Lou serves breakfast all day and house-made baked goods..

Outside, early-morning commuters hurriedly rush past the diner.

Inside, cheerful waitresses constantly refill your cup of coffee. The coffee is Lou’s own special blend with pure cream.

Timely tip: Make sure to order Lou’s signature donut holes.

Illinois (301 miles / 484 km)

The 30-foot /9m tall Gemini Giant greets guests arriving to the Launching Pad Restaurant (810 East Baltimore Street, Wilmington).

Springfield’s Maid-Rite Sandwich Shop (118 North Pasfield, Springfield) opened in 1921 with North America’s first drive-through window.

Cozy Dog Drive-In (2935 South 6th Street, Springfield) dishes out delectable deep-fried hot-dogs-on-a-stick of childhood dreams.

Several charming restored service stations beckon throughout the route.

Missouri (292 miles / 470 km)

Chain of Rocks Motel on the Mississippi river border between Illinois and Misouri at dusk, with the historic Route 55 neon signage all lit up in the sky

Closed to cars, the Chain of Rocks Bridge over the Mississippi River can be an atmospheric spot to stretch your legs.

When opened in 1929, the bridge design markedly stood out for its 30-degree turn over its short length.

Timely tip: If you stop to stroll or bike on the bridge, park on the Illinois side for security. Leave nothing in the car.

Ted Drewes Frozen Custard (6726 Chippewa Street, St. Louis) serves up “the concrete” upside down to customers since 1929.

The 66 Drive-In Theater (17231 Old 66 Boulevard, Carthage) shows movies al fresco from April to October.

Kansas (12.8 miles / 21 km)

Despite the short distance, the route through Kansas includes National and State landmarks.

Independent Oil and Gas Service Station (940 Military Avenue, Baxter Springs), formerly a 1930 service station, invites travelers into the Route 66 Visitors Center.

The lovely little Rainbow Bridge (between Baxter Springs and Riverton) spans Brush Creek  Architect and engineer James Barney Marsh patented this graceful design. Once there were other March Rainbow Arch Bridges on Route 66. Today only this 1923 bridge still stands.

Oklahoma (376 miles / 605 km)

Dusk skies, looking up at the Historic Route neon sign for Oasis Motel in Tulsa, OK

Unquestionably unmistakable in vibrant blue, the 80-foot / 24m Blue Whale (2680 North OK-66, Catoosa) sparks countless smiles since 1972.

Completed in 1898, the Round Barn (107 OK-66, Arcadia) remains a community center and popular photo-op. It’s garnered awards for its preservation.

Built in 1939 of sandstone, Rock Café (114 West Main Street, Stroud) dishes up comfort food featured on Food Network.

Timely tip: Rock Café’s gregarious owner Dawn Welch inspired Sally Carrera’s character in Pixar’s Cars.

Tulsa surprisingly impresses and equally delights with its distinctive Art Deco architecture.

The elegiac Oklahoma City National Memorial and Museum (620 North Harvey, Oklahoma City) evokes quiet contemplation and thoughtful reflection.

Texas (178 miles / 286 km)

World-famous Cadillac Ranch public art installation (13651 I-40 Frontage Road, Amarillo) encourages graffiti on 10 Cadillacs jutting nose-down and fins-up from the ground.

The Big Texan Steak Ranch (7701 I-40 East Access Road, Amarillo) dishes out a “free” 72-ounce steak challenge: Eat a 72-ounce steak, cooked to the contestant’s satisfaction; plus shrimp cocktail, baked potato, salad, and roll with butter. If it’s all is consumed within an hour, then it’s all free. Thankfully, the Big Texan dishes up smaller portions, too.

Once dilapidated, the Tower Station and U-Drop Inn (101 East 12th Street, Shamrock) has been painstakingly restored and renovated to original 1936 magnificence. The spacious complex includes a bustling café, visitors center, and museum.

New Mexico (380 miles / 610 km)

Tucumcari earns renown for its vintage architecture and neon signage along Route 66 Boulevard.

Beloved since 1939, the beautiful Blue Swallow Motel (815 East Route 66 Boulevard, Tucumcari) is well worth an overnight stay. Family owned and operated, Blue Swallow’s vintage rooms are immaculate.

Our One Detour

Here in the great state of the Continental Divide, Paul and I made the one and only deviation from the itinerary.

Why? Because eventually we both required a little break from driving for hours every day. Eating at roadside diners every meal. Sleeping in old motels, sometimes renovated and sometimes not, every night.

Paul, on one hand, especially needed espresso. I, on the other hand, yearned for a 5-star hotel, 24-hour room service, and a luxurious spa.

Thus we were thrilled that Santa Fe, one of the world’s great art cities, was nearby.

Without reservation, we rolled off the route and into town. This UNESCO Creative City enveloped us with relaxed luxury, excellent dining, and artistic aesthetic.

Afterward, refreshed from an undeniably restorative stay, we got right back on track.

Arizona (401 miles / 645 km)

Nearby the Petrified Forest National Park, find one of the nation’s three remaining wigwam villages:

  • No. 6 on Route 66 in Holbrook, Arizona
  • No. 7 on Route 66 in San Bernardino, California
  • No 2 in Cave City, Kentucky.

In 1950, the Lewis family built Wigwam Village Motel No. 6 (811 West Hopi Drive, Holbrook). Decades later, the family still owns and operates this Holbrook institution.

Pay homage to the Eagles’ song “Take It Easy” at the Standin’ on the Corner Park (523 West 2nd Street, Winslow).

You’ve seen the signs. At last, “Here It Is!” Hop into Jack Rabbit Trading Post (3386 Historic US 66, Joseph City) to peruse and procure every imaginable Route 66 souvenir.

Delgadillo’s Snow Cap Drive-In (301 East Chino, Seligman) dispenses 1953 kitsch, fun, laughter, and deliciousness in equal measures.

Timely tip: Bring your business card to Delgadillo’s.

California (315 miles / 507 km)

Cinephile Paul declares Bagdad Café (46548 National Trails Highway, Newberry Springs) essential for fans of the 1987 German film.

The late Elmer Long fashioned Bottle Tree Ranch (24266 National Trails Highway, Oro Grande) as a peaceful respite of whimsy, sustainability, and creativity.

Wigwam Village Motel No. 7 (2728 East Foothill Boulevard, San Bernardino) was the largest and last of Frank Redford’s patented wigwan properties. This 1950 village has been carefully and charmingly restored.

Timely tip: The Wigwam Motel’s mailing address is 2728 West Foothill Boulevard, Rialto. The actual physical motel address is 2728 East Foothill Boulevard, San Bernardino.

To the Finish

Santa Monica, California, is the official western terminus of Route 66.

The sun sets at Santa Monica Pier (200 Santa Monica Pier, Santa Monica). Commanding the foot of Coronado Avenue since 1909. Connecting to Route 66 since 1936.

The sky turns to twilight as you arrive, cruising underneath the landmark neon arch.

Bright lights begin to gleam and glimmer, silhouetting the Ferris wheel and rollercoaster.

Finally, you walk down the pier.

Past the Looff Hippodrome. All the way to the pier’s far end, overhanging the Pacific Ocean.

On this occasion, in this location, your Route 66 bucket list, start to finish, is complete.

So congratulate yourself on achieving this ultimate epic road trip, this legendary adventure.

Because you’ve explored, experienced, been inspired by it all on Route 66.


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