Route 66 Start to Finish: The Ultimate Epic Road Trip in the USA

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. On television shows. Films and animated movies. And catchy songs.

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

Together we’ll discover the bucket-list adventures, quirky attractions, and hidden gems across Route 66 through all eight states.

You’ll further find some fun and fascinating facts – in other words, “timely tips.”

This travel guide also includes a custom interactive map showing all the highlighted destinations, must-visit locations, and must-see sights along Route 66, end to end.

Plus, firsthand observations and candid recommendations from our own meaningful travel on the Mother Road.

Now, let’s explore, experience, and inspire your journey on historic Route 66, start to finish, the Main Street of America.

Ready? Buckle up, and let’s go!

Table of Contents

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Route 66 Start to Finish: Planning and Perspective

The Approach: Old School All the Way

Like travelers of bygone days, our inaugural Route 66 itinerary specifically outlined four parameters to recreate the historic experience as much as possible:

Firstly, no GPS.

Paper maps only. Well, paper maps and our much-read reference book Route 66: The Mother Road.

Secondly, no technology during the day.

Phones and laptops remained out of sight until after we checked into lodging for the night.

Thirdly, indie only with minimal “mod cons” (modern conveniences).

Historic motels, old-fashioned eateries, unique attractions, and mom-and-pop shops were the main attractions.

However, exceptions were allowed for museums, national parks, and national monuments on US Route 66.

Fourthly, no digital photography.

Photographer Paul shot everything on film and a vintage Nikon camera.

He then developed and hand-printed the negatives in the darkroom, and later digitized the photos.

The Jalopy: Caddy Daddy

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

The odometer read 6 miles when we 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.

Book your rental car on Booking or Expedia:

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.

The Why: What This Road Trip is Really About

We definitely did get our kicks on Route 66, start to finish. The what and the how of this ultimate epic road trip is, quite simply, bucket-list worthy.

What we found on the ultimate epic road trip were hidden gems galore. How Route 66 has defined quintessential travel adventures for a century.

Still, as we always say, “the WHY underscores everything.” So here’s our WHY:

Above all, we wanted to find the deeper meaning of the Mother Road, this Main Street of America. Get to the true heart of Route 66 from start to finish.

Because we purposed to understand not only the content but also the context and subtext of the legendary Mother Road. Gain a real sense of the past, present, and future on this Main Street of America.

In other words, discover what, how, and why 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.

Because it’s time to “motor west on the highway that’s the best.”

Route 66 Eastern Terminus: Chicago, Illinois

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

You’ll begin by fueling yourself up with the most important meal of the day at Lou Mitchell’s, a beloved Chicago eatery.

Since 1923, Lou has served hearty breakfast all day and house-made baked goods. Not to mention, free Milk Duds while you wait for your table.

Outside, early-morning commuters hurriedly rush past the landmark diner on the National Register of Historic Places.

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

Address: Lou Mitchell’s | 565 West Jackson Boulevard | Chicago, Illinois

Timely tip: Make sure to order Lou’s signature donut holes. They’re delicious!

Now, it’s time for your Route 66 bucket-list adventures to begin.

Settle into your jalopy. Fasten your seat belt. Start your engine.

The light turns green – and green means go! on your ultimate epic road trip.

Next, turn right from West Jackson Boulevard onto South Michigan Avenue.

Look for the official historic sign, marking the start of Route 66. Hooray, you’re on your way!

Address: Begin Historic Route 66 | 198 South Michigan Avenue | Chicago, Il 60603

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

The Gemini Giant, a 30-foot (9 m) tall roadside statue of an astronaut, greeted diners and passers-by at the Launching Pad Drive-In for many years.

The restored Gemini Giant is one of the Muffler Men, three-dimensional roadside advertisements from the 1960s.

Drivers, restaurant-goers, and passers-by cherished his silver helmet, silver rocket, green astronaut uniform, and his smile.

After the Launching Pad drive-in closed, the Gemini Giant moved into temporary storage in 2024. So, let’s hope he lands at his new Wilmington address on Route 66 soon.

Address: Gemini Giant | Address pending relocation | Wilmington, IL 60481

In Springfield, the Illinois state capital, the Maid-Rite Sandwich Shop opened in 1921 with a brand-new innovation:`

North America’s first drive-through window.

Can you believe you’ve discovered the original drive-through window?

Just imagine, this now ubiquitous everyday feature of ordinary modern life once made headline news in 1921.

Address: Maid-Rite Sandwich Shop | 118 North Pasfield | Springfield, IL 62702

In 1949, Ed Waldmire founded the Cozy Dog Drive-In with a tasty innovation that proved instantly popular: Deep-fried hot dogs on a stick.

Ever since then, generations of the Waldmire family have dished out delicious cozy dogs and house-made chili sauce.

These delectable cozy dogs and chili are still made with founder Ed’s original 1949 recipes.

Virginia Waldmire, the artistic wife of founder Ed, designed the cute logo of two cuddling hot dogs.

Her eye-catching logo still adorns keepsake Cozy Dogs souvenirs and the bright yellow roadside sign.

Address: Cozy Dog Drive-In | 2935 South 6th Street | Springfield, IL 62703

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

More than merely instagrammable places, the following Illinois Route 66 Service Stations are historic landmarks on the National Register of Historic Places:

Standard Oil Gas Station | 600 West Lockport Street | Plainfield, IL 60544

Ambler’s Texaco Gas Station | Route 66 and IL-17 | Dwight, IL 60422

Standard Oil Gas Station | 400 South West Street | Odell, IL 60544

Soulsby Service Station, circa 1926 | 102 South Route 66 Street | Mount Olive, IL 62069

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

Closed to car traffic for decades, the Chain of Rocks Bridge over the mighty Mississippi River can be an atmospheric spot to stretch your legs.

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

The bridge closed down in 1970 and then re-opened to pedestrians and bicyclists in 1998.

Today, the landmark Chain of Rocks Bridge is on the National Register of Historic Places for its engineering.

Address: Chain of Rocks Bridge | 10820 Riverview Drive | St. Louis, MO 63137

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.

Since 1929, Ted Drewes Frozen Custard has served up “the concrete” upside down to generations of happy customers in St. Louis.

Address: Ted Drewes Frozen Custard | 6726 Chippewa Street | St. Louis, MO 63109

The classic 66 Drive-In Theater shows outdoor movies from April to October – weather permitting, of course.

Address: 66 Drive-In Theater | 17231 Old 66 Boulevard | Carthage, MO 64836

Kansas Route 66 Start to Finish: 12.8 miles (21 km)

Despite the short distance, historic Route 66 through Kansas includes National and State landmarks.

Formerly a 1930s service station, the restored Independent Oil and Gas Service Station presently invites you into the Kansas Route 66 Visitors Center.

Stop in, say hello to the friendly folks, and perhaps meet some fellow like-minded travelers.

Address: Route 66 Visitors Center | 940 Military Avenue | Baxter Springs, KS 66713

Look for the lovely little Marsh Rainbow Bridge, also known as the Brush Creek Bridge, between Baxter Springs and Riverton.

In 1912, architect and engineer James Barney Marsh patented this graceful and resilient arched bridge design.

Address: Marsh Rainbow Bridge | Southeast Beasley Road | Baxter Springs, KS 66713.

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)

Unquestionably and unmistakably vibrant blue, the 80-foot (24 m) long Blue Whale has sparked travelers’ smiles since 1972.

So, take a rest break from the road at this big roadside attraction in a little pond. You can even walk through the Blue Whale’s huge grin for a fun photo op.

Address: The Blue Whale | 2600 North OK-66 | Catoosa, OK 74015

Completed in 1898, the Arcadia Round Barn remains active as a community center and popular photo-op. The 19th-century red rural landmark has garnered awards for its preservation.

Address: The Round Barn | 107 OK-66 | Arcadia, OK 73007

Constructed in 1939 of sandstone, Rock Cafe dishes up excellent American comfort food.

Rock Cafe and its owner, Dawn Welch, have been featured on Diners, Drive-Ins, and Dives on Food Network.

Dawn also inspired an especially memorable character in a much-loved animated movie series.

Address: Rock Cafe | 114 West Main Street | Stroud, OK 74079

Timely tip: Rock Cafe’s gregarious owner, Dawn Welch, inspired Sally Carrera’s character in the blockbuster Disney Pixar animated movie Cars.

Historic downtown Tulsa surprisingly impresses and equally delights with its distinctive Art Deco architecture from the 1920s and 1930s.

On a serious and solemn note, the elegiac Oklahoma City National Memorial and Museum evokes quiet contemplation and thoughtful reflection.

Address: Oklahoma City National Memorial and Museum | 620 North Harvey | Oklahoma City, OK 73102

Route 66 Start to Finish: Texas 178 miles (286 km)

The world-famous Cadillac Ranch public art installation features colorful graffiti on 10 vintage Cadillacs, all jutting nose-down and fins-up from the ground.

It’s a fun interactive stop for everyone – travel buddies, couples, and families with children. And a fun instagrammable photo op, too.

The owners encourage visitors of all ages and artistic abilities to paint on the Cadillacs.

So if you’d like to add your own graffiti, bring your own cans of spray paint and other supplies. Including a trash bag to clean up afterward.

Address: Cadillac Ranch | 13651 I-40 Frontage Road | Amarillo, TX 79124

Since the 1970s, fans from around the world have flocked to the Big Texan Steak Ranch and Big Texan Motel on Route 66:

Firstly, for an original neon sign of a larger-than-life cowboy outside The Big Texan Steakhouse.

Secondly, for its infamous “free” 72-ounce steak challenge seen in movies and TV shows such as Man V. Food and Anthony Bourdain No Reservations.

Challengers must eat a 72-ounce steak – cooked just so to the contestant’s instruction. As well as a shrimp cocktail, baked potato, salad, and roll with butter.

Everything, that is, counting down 60 minutes on the clock.

If it’s all consumed within the hour, whew! Then the entire meal is entirely free, and your money paid in advance is cheerfully refunded.

Rest assured, the Big Texan Steak Ranch certainly dishes up smaller portions, too.

Address: Big Texan Steak Ranch | 7701 I-40 East Access Road | Amarillo, TX 79118

Once dilapidated, the 1936 Conoco Tower Station and U-Drop Inn have been painstakingly restored and renovated to their original magnificence.

Additionally, the Art Deco landmark now includes a bustling cafe, visitors center, gift shop, and museum in the spacious complex.

Address: Tower Station and U-Drop Inn | 111 U.S. Rte 66 Shamrock, TX 79079

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

Tucumcari earns international renown for its vintage 20th-century architecture and abundant neon signage along Route 66 Boulevard.

Beloved since 1939, the Blue Swallow Motel is well worth an overnight stay.

Family-owned and operated, Blue Swallow Motel features vintage motel rooms updated with a few essential modern touches, such as free WiFi.

Friendly hospitality and a fabulous neon sign further make your stay memorable.

Address: Blue Swallow Motel | 815 East Route 66 Boulevard | Tucumcari, NM 88401

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 both thrilled when Santa Fe, one of the world’s great art cities, was near our historic Route 66 map route.

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, ample espresso, and cultural events. And, oh yes, a luxury hotel and spa to rest, relax, and recharge fully.

Afterward, refreshed from an undeniably restorative stay in Santa Fe, we got right back on track – and right back on historic Route 66.

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

Nearby the Petrified Forest National Park, you’ll 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 Chester Lewis family built the Wigwam Village Motel No. 6.

Decades later, the same Lewis family still owns and operates this authentic Holbrook institution.

The historic wigwams, complete with original furnishings and bathroom fittings, are entirely authentic to the 1950 experience.

Complete with a vintage car display, the Wigwam Motel surely is a one-of-a-kind place to stay.

Address: Wigwam Village Motel No. 6 | 811 West Hopi Drive | Holbrook, AZ 86025

Timely tip: The Lewis family also offers three more contemporary and accessible apartments adjacent to the historic wigwams.

On a corner in Winslow, Arizona, the timeless pop song “Take It Easy” comes to life at the Standin’ on the Corner Park.

The cute setting offers a large mural, an Arizona Route 66 ground sign, and a permanently parked red flatbed Ford – all inspired by song lyrics.

Life-size statues pay homage to Jackson Browne and Glen Frey who co-wrote the song “Take It Easy,” one of the Eagles’ greatest hits, in 1972.

Although it’s a modern roadside attraction, Standin’ on the Corner Park is one of the many instagrammable places on Route 66.

Address: Standin’ on the Corner Park | Corner of Kinsley & E 2nd Street | Winslow, AZ 86047

Mile after mile, kilometer after kilometer, you’ve seen the signs for Jack Rabbit Trading Post along Route 66.

Finally, there it is – a giant rabbit outside a long, low-slung building.

At last, “Here It Is!” Hop into Jack Rabbit Trading Post to peruse and purchase every imaginable Route 66 souvenir.

Address: Jack Rabbit Trading Post | 3386 Historic US 66 | Joseph City, AZ 86032

Delgadillo’s Snow Cap Drive-In dispenses 1953 kitsch, fun, laughter, and deliciousness in equal measure.

The awesome 1950s exterior highlights malts, shakes, creamy root beer, burgers, hot dogs, and fries – a classic diner menu. But Delgadillo’s Snow Cap Drive-In also offers tacos, burritos, and lighter fare, too.

Address: Delgadillo’s Snow Cap Drive-In | 301 AZ-66 | Seligman, AZ 86337

Timely tip: Bring your business card to Delgadillo’s Snow Cap Drive-in and add its to the huge collection. Add it to the huge collection on the walls, ceilings, and just about everywhere else.

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

Cinephile Paul declares Bagdad Cafe a must-see stop for aficionados of the 1987 German arthouse film.

The rustic timber-roofed A-frame exterior and correspondingly rustic interior evoke a rather cinematic and eclectic mood.

Address: Bagdad Cafe | 46548 National Trails Highway | Newberry Springs, CA 92365

The late Elmer Long fashioned Bottle Tree Ranch as a free and peaceful respite of whimsy, sustainability, and creativity.

Countless glass bottles and antique accents create outdoor sculptures aplenty and a special scene overall on two acres.

Address: Bottle Tree Ranch | 24266 National Trails Highway | Oro Grande, CA 92368

The classic Wigwam Motel is the seventh, the largest, and the last of Frank Redford’s patented villages.

Opened in 1950 as the Wigwam Village Motel No. 7, the motel today remains charming after restoration.

Air conditioning and a small swimming pool make the motel refreshing in the warm summer months.

Address: Wigwam Motel | 2728 East Foothill Boulevard | San Bernardino, CA 92410

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 Western Terminus: Santa Monica, California

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

As you pull into this coastal city near Los Angeles, the sun is setting at Santa Monica Pier.

Since 1909, this picturesque pier has commanded the foot of Colorado Avenue.

Since 1936, it’s completed the westernmost point of the former federal highway system known today as Historic Route 66.

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.

Address: End Historic Route 66 | 321 Santa Monica Pier | Santa Monica, CA 90401

Route 66 Start to Finish: In Conclusion

Now that you’ve crossed all eight 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, the ultimate epic road trip.

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Interactive Map of Route 66 Start to Finish

Route 66 Resources

Cars 1, Cars 2, Cars 3. Directed by John Lasseter and Brad Lewis, starring Owen Wilson, Bonnie Hunt, et al. Disney Pixar, 2021.

National Park Service Travel Route 66.

Ross, Jim and Jerry McClanahan, Here It Is! The Route 66 Map Series. Ghost Town Press, 2021.

Takeya Insulated Stainless Steel Coffee Travel Mug (17-ounce mug and 24-ounce mug fit most cupholders).

Wallis, Michael, Route 66: The Mother Road 75th Anniversary Edition. St. Martin’s Griffin, 2001.

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Route 66 Start to Finish: FAQs

All opinions expressed are Spotlight Sojourns’ own.

All content and images are original, created with care by yours truly, Marilee Kostadimas and Paul Kostadimas, not AI. We’re the Hidden Gemologists of Spotlight Sojourns: Award-winning travel experts, storytellers, and advocates of meaningful travel. Because meaningful travel is part of a meaningful life. And stories enrich the meaning.

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