Route 66 Start to Finish: The Ultimate Epic Road Trip

Route 66, start to finish is the ultimate epic road trip in the United States. It’s a legendary adventure across eight states, from Illinois in the east to California on the West Coast.

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

So let’s take a journey unlike any other, over thousands of miles on the Main Street of America.

Come explore, experience, and be inspired with us from start to finish on the Mother Road.

Ready? Buckle up, and let’s go!

Route 66 Start to Finish: Planning and Perspective

The Approach: Old School All the Way

Like travelers of bygone days, our Route 66 itinerary specifically outlined four parameters:

Firstly, no GPS. Paper maps only.

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

Thirdly, indie only. Minimal mod cons.

Historic motels, old-fashioned eateries, unique attractions, and mom-and-pop shops were the main attractions. Exceptions made for museums, national parks and national monuments on U.S. Route 66.

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

The Jalopy: Caddy Daddy

A brand new, fully loaded, gleaming white Cadillac conveyed us in luxury, style, and comfort on this iconic road trip.

The odometer read 6 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.

The Itinerary: East to West

The traditional Route 66 experience flows east to west:

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

For seasonal timing, Spring and Autumn are typically the best times to drive the entire Route 66, start to finish from east to west.

Because, at this time, the weather is generally temperate and pleasant across all 8 states.

So, we planned our drive for late September through early October.

Our full itinerary on Route 66, from beginning to end, took 2.5 weeks overall.

However, you may certainly drive in either direction, along any section, and for as short or as long a road trip as you choose.

The Experience: Real, Genuine, Authentic

The best thing about the Route 66 experience is the Route 66 community: Real, genuine, authentic.

Sincere smiles and friendly hellos greeted us wherever we went. From historic motels, old-fashioned diners, and quirky attractions to museums, national parks, and national landmarks.

The warm-hearted welcome also extended to our one unexpected detour from Route 66. Keep reading this article for more about this unplanned location.

Our Why: What It’s Really About

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

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

We wanted to find the hidden gems. Get to the true heart of Route 66 from start to finish.

With this purpose in mind: To understand not only the content but also the context and subtext of the legendary Mother Road. The past, present, and future of this Main Street of America.

In other words, discover what Route 66 is really about the places, the people, their stories.

Route 66 Start to Finish: Top Stops and Timely Tips

Colorful restorations, unique attractions, and neon signs enliven the environment everywhere along the route.

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

Ready? Let’s go!

Route 66 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: Route 66 Start to Finish 301 miles (484 km)

The Gemini Giant, a 30-foot (9 m) tall roadside statue, greets you at the Launching Pad Restaurant (810 East Baltimore Street, Wilmington).

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

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

Timely tip: Keep an eye out for several nicely restored service stations along the route.

Missouri: Route 66 Start to Finish 292 miles (470 km)

Now that it’s closed to car traffic, 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, locals recommend parking on the Illinois side for security. Additionally, leave nothing in the car.

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

The 66 Drive-In Theater (17231 Old 66 Boulevard, Carthage) shows outdoor movies from April to October. Weather permitting, of course.

Kansas Route 66 Start to Finish: 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.

Timely tip: Once there were other March Rainbow Arch Bridges on Route 66. Today, only this 1923 bridge still stands.

Route 66 Oklahoma Start to Finish: 376 miles (605 km)

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.

Route 66 Start to Finish: 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 consumed within an hour, whew! 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) have been painstakingly restored and renovated to their original 1936 magnificence.

The spacious complex includes a bustling cafe, visitors center, and museum.

Route 66 Start to Finish: New Mexico 380 miles (610 km)

Our One Detour off Route 66

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 pampering spa treatments.

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

Lack of hotel reservations notwithstanding, we rolled off the route and into town.

This UNESCO Creative City enveloped us with vibrant aesthetics and artistic inspiration at galleries galore.

Santa Fe further delivered excellent dining and ample espresso. And, oh yes, a luxury hotel and spa.

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

Route 66 Start to Finish: Arizona 401 miles (645 km)

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

• Wigwam Village Number 6 on Route 66 in Holbrook, Arizona
• Wigwam Village Number. 7 on Route 66 in San Bernardino, California
• Wigwam Village Number 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 purchase 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 and add its to the huge collection.

Route 66 Start to Finish: California 315 miles (507 km)

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

The late Elmer Long fashioned Bottle Tree Ranch (24266 National Trails Highway, Oro Grande) is 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 wigwam 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.

Route 66 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 when 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, your Route 66 bucket list is finally complete in this location.

Route 66 Start to Finish: In Conclusion

Now that you’ve crossed 8 states, it’s time to congratulate yourself.

Because you have completed Route 66, start to finish, the ultimate epic road trip in the United States.

You discovered what the Mother Road, the Main Street of America, is really about.

With the result that you fulfilled the purpose, the WHY of this entire legendary adventure:

You found the hidden gems. You got to the true heart of Route 66: the places, the people, and their stories.

Because you have explored, experienced, and been inspired by Route 66, start to finish.

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