Route 66 Self Guided Motorcycle Tour

Day 1
Chicago Arrival

Depart London Heathrow – 11:50
Arrive Chicago – 13:55
Journey Time – 8 hours 30 minutes

Upon arrival into Chicago O’Hare airport proceed to your overnight hotel located in downtown Chicago, here you can begin your own historic ‘road trip’ after settling in. Chicago’s famed Magnificent Mile, Michigan Avenue, Watertower Place, the Navy Pier, the Merchandise Mart, Shedd Aquarium and the Field Museum are not far away.

As you explore one or a selection of these world class attractions, you can begin thinking about your upcoming journey on the Mother Road. Although Route 66 virtually parallels the interstate anywhere portions of the actual road exist, even today hundreds of men & women, young and old, take this trip every year from Chicago to Los Angeles. America unfolds as you travel through the Ozarks, authentic American towns in southwest and vast open deserts. You can start your trip at Grant Park, the exact place where Route 66 begins.

Route 66 through Illinois was first used by Native Americans as a trading path followed by fur trappers and traders who sought a path to the Mississippi River to ship their goods downstream to French New Orleans. Al Capone and the rumrunners kept the road busy right after it became the first fully paved highway in Illinois in the early 1920s. When the old Route 66 road signs came down in 1977, the strong relationship of the road to the people who travel it brought new Historic Route 66 signs back almost immediately. When the highway department would not pay for them, bake sales, auctions, festivals and other truly American events raised money to bring them back.

Overnight – Chicago

Below is a video detailing what you will see in Illinois from Chicago to Springfield 

Day 2
Chicago to St. Louis
300 miles

This morning you will collect your bike.

Most of today will be spent traveling through Illinois farmlands on your way to St. Louis, the crossroads where highways from Chicago, Kansas City, Memphis, Nashville, and Indianapolis meet. The city was originally the focal point of Indian trails that ran all across the US and the jumping off point for Lewis and Clark’s Expedition of Discovery to open the West through the newly acquired Louisiana Purchase. It will also be your jumping off point to points south and west, as you begin your journey through the wide open spaces.

Springfield, the Illinois State Capital, is Abraham Lincoln country. He left here to serve as President of the United States during the most awful period in American history, the Civil War and returned as a fallen hero, a casualty of the same war. New Salem where Lincoln lived and worked for six years has been reconstructed. Costumed interpreters bring the village alive. The Lincoln Home National Historic Site is the centerpiece of a four block historic neighborhood. The President’s Tomb, Presidential Library and original law office are also open for touring.

As you cross from Illinois into Missouri you’ll be crossing the historic Chain of Rocks Bridge. Be sure to stop at Ted Drew’s Frozen Custard, serving Route 66 travelers since 1929. In St. Louis, the original Route 66 tracked through town very near the Gateway Arch and we definitely recommend riding the elevator inside Arch to the top of the 630 foot structure. Spectacular views of the Mississippi River await. In the evening, you can catch up with the St. Louie Blues, which were born right here and taste the fruits of Anheuser-Busch, the world’s largest brewer.

Overnight – St. Louis 

Day 3
St. Louis to Springfield
210 miles

Route 66 from St. Louis to Springfield, Missouri takes you through the lush rolling hills of the Missouri Ozark Mountains. The road follows the Great Osage Trail, a major Indian path across the state and a route used by Jess James, of famed James Gang fame, who locals knew as ‘just a nice Missouri boy!’ One of the most famous attractions on Route 66, Meramec Caverns was also used by the James Gang as a hideout when escaping the law. Lester Dill who owns Meramec Caverns started the American advertising institution, the bumper sticker, when he gave away portable advertising to all who stopped by to visit.

Much of the rural Ozark region, punctuated by the second oldest mountains in the world, looks much as it did when the first settlers arrived. Springfield has been bustling since the St. Louis-San Francisco railroad arrived in 1870. Even though most of Route 66 through here is now Interstate-44, remnants of the old road are everywhere just off the highway.

Interestingly, Springfield is considered the mother of the Mother Road itself. It was here that Cyrus Avery of Oklahoma who fought for a route through Oklahoma met with John Woodruff of Springfield, to plan and promote the idea of an interregional link that would bring trade and access to the area. In honor, Springfield has preserved much of the old highway frontage along St. Louis Street as well as the ‘Chestnut Expressway.’ If you’re a fan of western lore, delve into the ‘Wild’ Bill Hickock legend surrounding his fellow gambler Dave Tutt. There are so many different stories no one really knows what happened.

Overnight – Springfield

Day 4
Springfield to Tulsa to Oklahoma City
310 miles

Oklahoma was the home of Cyrus Avery, who came to be known as the ‘Father of Route 66.’ After he was appointed to head the commission that reviewed the routes of new national highways, he fought for several years to bring a major highway through his home state, knowing it would boost the economy. Ultimately, he was successful in the choice of a route that followed the National Old Trails Road in 1925, which just happened to cross right through the middle of Oklahoma.

‘Been on this road for a mighty long time,
Ten million men like me,
You drive us from you’ town
We ramble around
And got them 66 Highway Blues.’

Woody Guthrie of ‘This Land is Your Land’ fame who hailed from Oklahoma, illustrated the icon which Route 66 had already become in a song that told of the plight of the Okies fleeing to California. The Los Angeles police stationed themselves at the Arizona border in 1934 to stop the flood of Dust Bowlers looking for a better life.

Southwest of Springfield, you’ll begin to see why they would leave, as the landscape changes from the rich crop raising Midwest into the American southwest; red, dry and dusty. During the1930s, more than 15% of Oklahoma’s population took Route 66 to escape the constantly blowing sand. They picked up their belongings, their families, their hopes and their dreams and headed west.

After World War II, the pretty Oklahoma City referred to by the Nat King Cole in ‘Get Your Kicks on Route 66’ rose to new heights during the oil boom (the State Capitol is the only one in the country with an oil well on the grounds), only to suffer a dramatic decline at the end of the 1980s. Since then, the city has gone through an astounding transformation which continued during the re-building which followed the Oklahoma City bombing in 1995. The monument to the victims is very moving and an adjacent museum tells the story.

For nightlife, make sure you visit Bricktown, a former warehouse district that has been reinvigorated with restaurants, cafes, night clubs and a vibrant atmosphere.

Overnight – Oklahoma City

Day 5
Oklahoma City to Amarillo
260 miles

For the traveler going west on Route 66, Texas is Cowboy Country. It is here that some of the most wonderful icons of Route 66, those ‘functional simple buildings that were adorned with all manner of exterior signs promising all things larger than life, still exist. Two headed snakes, reptile farms, alligators, wondrous caves and petrified mummies all vied for the attention of the vacationer in a unique side show that would have made P. T. Barnum proud. The tales carried home from these vacations would entice and amaze the neighborhood for months.

Amarillo is one of the last places on earth where the Old West is just minutes away or depending on where you are, could be closer than that. The vast ranches of the Texas Panhandle, some numbering in the millions of acres are just outside of Amarillo. Shortly after being discovered by Spanish explorer Francisco Coronado in 1541, the area became a magnet for cattlemen and sheep herders from all points of the compass looking for fresh grazing grounds. As the Dust Bowl farmers headed to California, more cattlemen and cowhands moved in to claim the same territory for ranching. Step into ‘The Real Texas’ as the locals say.

Today, Amarillo and the surrounding Panhandle area is still a unique blend of the Old West and the New West, populated by American cowboys, roughnecks and self made millionaires and the ever present oil derricks. Working ranches, essentially unchanged from the day-to-day operations of the late nineteenth century peacefully coexist with a vibrant twenty-first century economy powered by petroleum. More than 2 million cattle are still shipped out of Amarillo each year. Make sure to drive Amarillo Boulevard which is the original Route 66 that is still lined with block after block of strip shopping centers and roadside motels straight out of the 1950s.

Overnight – Amarillo

Day 6
Amarillo to Tucumcari
120 miles

For many people traveling the old Mother Road during its hey-day, New Mexico presented their first glimpse of the more exotic cultures of the Southwest. To people who had never left the Midwest before, it was as if they had entered another country. Back then, the Native American and Spanish cultures were much stronger, not having been diluted as much with contemporary life. It was a fascinating heritage of old Indian Pueblos that dated back to before European colonization and Santa Fe and Albuquerque that looked like they could have fallen straight out of Mexico with adobe buildings and a Spanish plaza in the middle town. What adventure and discovery these lands presented; a phenomenal contrast to Middle America.

Unique to New Mexico also was the number of Mom and Pop businesses that sprung up along Route 66. Some are still there. More amazing are the materials used to create workable spaces for the businesses. Crates left over from World War II became the walls of a motor court. Oilcans became shingles used to roof a service station. Cast away bottles and roadside trash became the material to create a wondrous roadside attraction. Diners could be ordered from a catalog and shipped by railroad to their destination. These are the same icons we marvel at along the road that so represented America’s love affair with the automobile. As a result, New Mexico still has the most miles of original Route 66 that can be driven today.

On your way between Amarillo and Tucumcari, New Mexico, be sure to stop at Cadillac Ranch to see the ten tail- finned Cadillacs buried in the sand.

Once nicknamed ‘Six-Shooter Siding,’ Tucumcari, New Mexico got its start in 1901 as a rowdy railroad camp filled with saloons and outlaws. Soon, it became one of the many small railroad towns in the southwest with a flagging economy and diminishing population. Today, Route 66 is critically important, since it was the new businesses that were established along Route 66 which allowed Tucumcari to hang on, when other towns failed completely. Realizing that they have one of a handful of authentic roadside towns still intact and thriving has promoted a renaissance and revival among the gentlemen and businesses who just refused to let this wonderful piece of Americana and the American ‘road trip’ pass away entirely. Let the signs that read ‘Tucumcari Tonight!’ beckon you to this interesting place.

Overnight – Tucumcari

Day 7
Tucumcari to Albuquerque
180 miles

Next up, Albuquerque – New Mexico’s capital city. Younger than its more northerly counterpart, Santa Fe, Albuquerque was founded in 1706 by a group of Spanish colonists who were granted permission by the King of Spain to establish a new city on the river. Old Town Plaza was the result of Spain’s Laws of the Indies which required setting a plaza at the center of any city. This Plaza still fronts the San Felipe Neri Church complex built in 1793 and the El Camino Real, the main route through town that connected Santa Fe and Albuquerque with Mexico City. The Santa Fe Trail also criss-crossed the region in 1821. Today, both routes are National Scenic Byways and All American Roads.

Historic neon signs still glow on the old Route 66 through Albuquerque which is now Central Avenue. Alongside the vintage signs, you’ll see new versions put up by businesses that are continuing the aesthetic traditions of the old Route 66, adorning their shops with bright buzzing neon. The famous Route 66 continues to guide visitors through Albuquerque from the volcanoes on the city’s far west side past the Rio Grande Botanical Garden and the Albuquerque Aquarium through the historic Old Towns and Downtown business districts and continuing eastward through the University of New Mexico and trendy Nob Hill, where you’ll find many of the city’s best restaurants, distinctive shops and boutiques.

Overnight – Albuquerque

Day 8
Explore Albuquerque

As you complete the self-guided Historic Walking Tour from Plaza to Plaza, you will be passing from Old ‘Villa Albuquerque’ in Old Town, to the Downtown Civic Plaza, created in 1972. In between, you will witness 300 years of history.

It will be challenging to determine which other places to visit. Sandia Peak Tramway takes you over 2.5 miles to the 10,000 foot peak of the Sandia Mountains. Visit the New Mexico Museum of Natural History and Science, the Indian Pueblo Cultural Center, Albuquerque Museum and the National Hispanic Cultural Center to learn more about local culture and history. Petroglyphs at the Petroglyph National Museum and El Morro National Monument reveal the life of ancient peoples who inhabited the area. The National Atomic Museum and Trinity Site, the exact spot where the first atomic bomb was detonated tell the story of this momentous event in American history.

Alternatively take a drive North East (approx 64 miles/1 hour) along Highway 25 to historic & cultural Santa Fe.

Overnight – Albuquerque

Day 9
Albuquerque to Holbrook
230 miles

On the way between Albuquerque and Holbrook, you’ll be entering the dramatic lands of western New Mexico and ultimately traveling through the Navajo Reservation. The New Mexico Mining Museum at Grants has replicated an entire uranium mine. Natural attractions include the El Malpais National Monument, the Continental Divide. The excavated Pueblo at Inspiration Rock dates back to AD 1200. Skirting the southern foothills of the Zuni Mountains, the drive along Highway 53 is likely the most scenic in all of New Mexico.

Staying on this route brings you to Gallup, you can follow Hwy 40/Route 66 thru Gallup for about 9 miles until you reconnect with I-40. The Rex Museum in downtown Gallup offers local history including the WWII saga of the Navajo code talkers and Route 66 of course. Crossing into Arizona this part of the highway runs through a canyon with dramatic scenery. At Lupton you can see the Giant Tee Pee Trading Post whose Native American arts and crafts are made locally. Watch for the exits for Painted Desert and Petrified Forest before arriving to Holbrook. In Holbrook stop at the Wigwam Motel for a picture in front of the teepee motel rooms.

Overnight – Holbrook

Day 10
Holbrook to Williams
125 miles

Just outside Joseph City you finally reach the famous Jackrabbit Trading Post whose iconic billboards are plastered 1000 miles along Route 66. Take your picture beside of or on top of the giant jackrabbit! At Winslow see the “Standing on the Corner” statue dedicated to the Eagles song “Take it Easy”. Reaching Flagstaff you leave Highway 40 for the Grand Canyon National Park. The Grand Canyon is not actually on Route 66 but you couldn’t miss an opportunity to see one of the Seven Wonders of the World! After experiencing the grandeur of the Grand Canyon continue back to Route 66 and your overnight destination Williams. Williams is a beautiful mountainside town where soda fountains, quirky motels and diners line the mother road as it was back in the day. Williams is proud of their nightly (7:00 pm) gunfight with the world famous Cataract Creek Gang, known for their raucous, rambunctious behavior, as they shoot it out in the streets of Williams.

Overnight – Williams

Day 11
Williams to Las Vegas
216 miles

Ahead of you lays the longest unbroken portion of the “old road”. It runs from Seligman all the way to Topock, at the California border. Completely bypassed by I-40, it’s as unspoiled as any section of the road anywhere. The historic Route 66 runs North and curves back to the interstate in Kingman, where you can connect with Highway 93 to Las Vegas. The Route 66 detour is only about 15 miles / 24 kilometers longer, but it’s of course slower to drive than the interstate. The road passes through small towns like Peach Springs, Truxton and Hackberry in the Hulapai Indian reservation. As you approach Peach Springs, look to the north. There is a point where you can see all the way to the south rim of the Grand Canyon, which makes it closest approach to the highway in this area. Finish your day at Las Vegas, the neon oasis that never sleeps!

Overnight – Las Vegas

Day 12
Explore Las Vegas

The Las Vegas Strip, now an All American Road and National Scenic Byway, is a sparkling fantasyland at the heart of the city. Its unique blend of exciting entertainment, scenic beauty, and lavishly landscaped resorts take you to a wide variety of exotic realms from a medieval castle to a Parisian sidewalk cafe, a lakeside Italian village, or a pyramid in ancient Egypt. Once you arrive on the Strip, however, you might be surprised to find that it’s also an enjoyable walking environment. Whether it’s pirates plundering, fiery volcanoes spouting or tropical gardens luring the weary, the Las Vegas Strip offers a variety of fascinating visual experiences. Las Vegas is home to some of the most spectacular shopping in the world. The Forum Shops at Caesars is Las Vegas’ premier luxury retail destination offering top retail, dining, entertainment, location and thematic Roman ambiance. And with two distinct locations together featuring 290 designer and name-brand outlet stores, Las Vegas Premium Outlets® is a must stop for savvy shoppers.

Overnight – Las Vegas

Day 13
Las Vegas to Santa Monica / Los Angeles
290 miles

Finally, after a journey through the Mojave Desert today, you’ll reach the bright lights of Hollywood. It may be hard to believe that the area around Barstow was once covered by immense lakes ringed with Native American villages. When silver was discovered in Calico, the area became a mining center that included borax mining. Route 66 is
Main Street through Barstow. Just off Main on First Street, you’ll discover the original Harvey House which gave rise to hospitality complexes all over the southwest.

Rainbow Basin about 15 miles north of Barstow is one of the lakebeds that existed between 10 and 30 million years ago. Calico Ghost Town is California’s official Silver Rush Ghost Town, preserving one of the few original mining camps in the Old West. One third of the town is original with the rest constructed in the ‘spirit’ of Calico’s Old West past. Today’s destination, Santa Monica is where the Mother Road meets the Pacific Ocean at the Pier. Many a dream has begun and ended on those beaches.

Overnight – Los Angeles

Day 14
Explore Los Angeles / Santa Monica

The sky’s the limit in Los Angeles. Take a go-behind-the scenes tour at Universal Studios Hollywood, visit the UCLA Armand Hammer Museum which presents the work of unprecedented artists, the California Heritage Museum, the Autry National Center Museum of the American West, the Aquarium of the Pacific, Los Angeles Zoo and Botanical Gardens. Be sure to visit the new Getty Center perched high on a hill atop the city. The view doesn’t get much better than that. Or if none of those things suit you, you can always go to Disneyland! But be sure to call in at The Outlets at Orange 40 minutes from Los Angeles Airport and less than four miles away from Disneyland, to bag some last-minute bargains!

Overnight – Los Angeles

Day 15
Depart Los Angeles

Make sure you take some time to relax in the California sunshine before you catch your plane Savor your journey to the bright lights of California all the way home.

Depart Los Angeles – 17:45
Arrive London Heathrow – 12:00 (Next Day)
Journey time – 10 hours 20 minutes

Additional Stops for Route 66 motorcycle 21 night itinerary

Chicago, Illinois – 1 extra night (2 in total)

There’s so much to see in this iconic city – famed Magnificent Mile, Michigan Avenue, Watertower Place, the Navy Pier, the Merchandise Mart, Shedd Aquarium and the Field Museum to name but a few!

Springfield, Illinois – (Not to be confused with Springfield, Missouri already included) – 1 night

Explore the legacy of Abraham Lincoln.

St Louis, MO – 1 extra night (2 in total)

Try your hand at some science experiments, interact with butterflies or immerse yourself in a little arts and culture – it’s all in a day’s fun in St. Louis, Missouri. From sports and shopping – to tours and attractions.

Santa Fe, New Mexico – 2 nights

One of the original routings of Route 66 that was abandoned went through Santa Fe, the capital city of New Mexico which was established 13 years before Plymouth Colony was settled by the Massachusetts Company. The city began with a handful of European style dwellings constructed by Spanish settlers and soon became the seat of power for the Spanish Empire north of the Rio Grande River. It began to prosper when Don Pedro de Peralta settled in 1610, the same year that Hampton, Virginia, the oldest continuous city on the East Coast, was settled. Santa Fe served as the capital of the Spanish Kingdom of New Mexico, the Mexican province of Nuevo Mejico, and the capital of the New Mexico Territory.

Once you arrive, it will be challenging to decide which locations to visit. Everything is focused on the Plaza, the center of the historic downtown. We suggest visiting the Palace of the Governors, the oldest public building still in use in America, constructed in 1610. It is now a southwestern history museum. The Museum of Fine Arts, next to the Palace, is older than the state itself. The extensive collection of southwestern art also includes paintings by Georgia O’Keefe, who called Santa Fe home for many years.

There are cultural museums of many other varieties, including the Museum of Spanish Colonial Art, the Wheelwright Museum of the American Indian, the Museum of Indian Arts and Culture, the Georgia O’Keefe Museum, and World Folk Art, with diverse works from artisans all over the world. If that’s not enough, there a huge list of art galleries, a myriad of restaurants and other interesting shops. Enjoy whatever you choose to do, there is more than enough to fill two days.

Grand Canyon – 1 extra night (2 in total)

Take a full day to explore the South Rim of the Grand Canyon National Park. First stop should be the Visitor Centre located at the South Rim Village. Here you can pick up information on short hikes, special areas that you may wish to visit during the day and helicopter or airplane rides over the Grand Canyon. A visit to see the El Tovar Lodge if you are not staying there is a must, but we also suggest any of the scenic stops or even taking one of the guided coach tours that will explain the history and geology of the area. Another must is a visit to the IMAX Theatre located close to your hotel for a thrilling 3D show based around the Grand Canyon.

We strongly suggest you that spend one of your evenings and maybe even an early morning at the Grand Canyon Rim to experience the spectacular sunrise and sunset.

Los Angeles – 1 extra night (3 in total)

There’s so much to see and do in this amazing city… Take a tour of Los Angeles and Movie Stars Homes, the Hollywood Trolley Tour, the California Science Center, the Music Center, the Japanese American National Museum, the Museum of Contemporary Art Grand Avenue, the Simon Wiesenthal Center and more.