Historic Route 66

Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California

Projected: September 29-October 17, 2020 • 19 Days • Price TBA

Join us as we trace the Mother Road from Chicago to Santa Monica, reliving American history as we wind our way through 8 states from Illinois to California!

Traveler Rewards Program: New Travelers receive a $200 discount on the Historic Route 66 tour! Returning travelers receive our Alumni Traveler Discount of 5-10% off the main tour price. Terms, exclusions and conditions apply. Check out our Traveler Rewards page for more details.

Now accepting Early Bird deposits on this potential 2020 tour! An Early Bird is a $50 deposit that holds your spot during the planning stages of a trip, when we don’t have a set itinerary or dates. Early Birds are always refundable!

Established in 1926, the “Mother Road” started in Chicago and wound its way for 2,488 miles through Illinois, Missouri, Kansas, the panhandle of Texas, New Mexico, and Arizona, before finishing in southern California at the Pacific Ocean. John Steinbeck featured Route 66 in his epic novel Grapes of Wrath, as the Joad family fled the hopelessness of Dust Bowl Oklahoma in search of jobs in California. The road gained fame with the hit song “Get Your Kicks on Route 66” and the popular television show—Route 66. It became emblematic of the unity and diversity of the land of America, and a trip along its length is nostalgic, thought-provoking, and full of old fashioned fun.

Route 66 Update

Our guides have just completed the scouting trip, and are working on finalizing this itinerary. Here are a few new updates from their time along the trail!

  • Scenic new nature walk in Palo Duro Canyon State Park, “the other Grand Canyon,” south of Amarillo, Texas
  • Outstanding multi-part hike at spectacular Petrified Forest National Park
  • A stop in a Route 66 ghost town – not a soul left!
  • Stay in a classy 1890s hotel in a delightful old New Mexico Spanish town on the old Santa Fe Trail
  • World-class walk along the South Rim of the majestic Grand Canyon
  • New and improved walk routes available throughout the tour
  • Two night stay in a delightful Route 66 town (A new guide favorite!) in Arizona
  • Multiple new heritage stops along Historic Route 66

More details coming soon!

This is a draft itinerary reflecting our last tour of Route 66. Research by our tour planning team will be needed to determine which Route 66 sites are currently active. An updated itinerary with dates and pricing will be made available!


  • All land travel as outlined
  • Tourist-class hotel accommodations
  • 22 meals – All breakfasts, 3 lunches and 3 dinners as listed in itinerary (BLD)
  • 12 walks as listed
  • Walk fees for those collecting AVA Credit
  • WAI guide service throughout (2 guides)
  • All tipping for local guides, coach drivers, and group meals
  • Pricing is based on double occupancy; single accommodations are available for a fee.

Entrance fees/Activities:

  • Amish Interpretive Center, IL
  • Amish countryside guided tour & lunch, IL
  • Abraham Lincoln Museum, IL
  • Abraham Lincoln Presidential Library, IL
  • Wilson’s Creek National Battlefield, MO
  • Oklahoma City National Memorial, OK
  • Will Rogers Memorial Museum, OK
  • Route 66 Museum, OK
  • Devil’s Rope Museum, TX
  • Texas ranch dinner experience, TX
  • Albuquerque Balloon Fiesta – Mass Ascension, NM
  • Acoma Sky City Pueblo, NM
  • Meteor Crater, AZ
  • Route 66 Museum, CA
  • More fun, interesting, and educational stops than we can list!

Adventure Pace

Tour Pace: 1 2 3 4 5
Walk Challenge: 1 2 3 4 5

Important Info

Group Size

25-30 travelers


Strategically located Tourist Class hotels or better


Breakfasts included with a selection of lunches and dinners. Letters BLD indicate which meals are included.


Not included. Travelers will fly into Chicago, IL and fly home from Los Angeles, CA.


Included. We use full-size motorcoaches with a seating capacity of 40+ seats.

Traveler Age

Our travelers usually range from 50–75 years of age. All ages welcome!


This is a draft itinerary reflecting our last tour of Route 66. Research by our tour planning team will be needed to determine which Route 66 sites are currently active. We plan on adding 2 more days to this itinerary, and an updated itinerary with dates and pricing will be made available soon!

Click on each day for more details.

Day 1: Arrive Chicago, IL

Our Adventure along Route 66, referred to by John Steinbeck as “the mother road” and “America’s Main Street,” begins today in Chicago. The only activity planned for today is a “Get Acquainted” briefing at our hotel around 7:30 pm

Day 2: Chicago–Bloomington, IL (BD)

Chicago Windy City Walk, IL – 11 km, rated 1A

Today’s activities start with breakfast at Lou Mitchell’s Restaurant, a Chicago institution since 1923. Our walk includes Windy City classics like the Shedd Aquarium, the Field Museum, the John Hancock Building, and the Magnificent Mile along Michigan Avenue. Following the walk, our pilgrimage–a 2,400 mile odyssey to Santa Monica, California, where the road ends–begins with a stretch southwest along the original road to dinner at the Old Log Cabin Inn in Pontiac.

Day 3: Bloomington-Springfield, IL (BL)

Breakfast at Dixie Trucker’s Home shows us how an icon of Route 66 started in 1928 from a converted garage and has adapted through 75 years of change. Further south in Amish country, we visit the Amish Interpretive Center, then take a drive through the countryside of the Amish community in Illinois, learning about the local lifestyle and culture from our guide as we pass Amish homes, businesses, farms, and schools. Following lunch in an Amish home (homemade everything!), the lady of the house shows us through her home, describing daily tasks and detailing their form of worship. Leaving idyllic Amish country, we spend the night in Springfield, Illinois, home of Honest Abe. You may have time to visit the new Abraham Lincoln Museum or Abraham Lincoln Presidential Library, or you may choose to include this in tomorrow’s walk route.

Day 4: Springfield–St. Louis, MO (B)

Abe Lincoln Springfield Walk, IL – 10 km, rated 1A

Our Springfield walk traces the heritage of Abraham Lincoln with stops at Lincoln’s Tomb, the state capitol, and the Lincoln Home. After a stop for a Route 66 lunch (not included) at Cozy Dog Drive-In, where corn dogs were first created, we’ll cross the border to St. Louis, with a stop en route at the Chain of Rocks Bridge.

Day 5: St. Louis–Rolla, MO (B)

St. Louis Amazing Arch Walk, MO – 10 km, rated 1A

This morning’s walk features the city that was considered a major gateway to westward migration in the century before Route 66. Our walk route in St. Louis passes both the Jefferson National Expansion Memorial (free admission) and the famous Gateway Arch (admission not included), before our mid-afternoon departure along the Old Road.

Day 6: Rolla–Miami, OK (BL)

Wilson Creek National Battlefield Walk, MO – 10 km, rated 2A

Route 66 leads us diagonally across Missouri to Wilson’s Creek National Battlefield, site of one of the most important early battles in the Civil War. Following our walk, and an enlightening visit to the National Parks interpretive center, we’ll enjoy a down home lunch at a fun eatery nearby before continuing along the highway into Oklahoma.

Day 7: Miami–Edmond, OK (B)

Riverton Rainbow Bridge Walk, KS – 10 km, rated 1A

The state of Kansas lays claim to only 13 miles of the Route, and we’ll cover a good percentage of that on this morning’s walk that includes a stroll across Rainbow Bridge, a classic Route 66 landmark. A lunch break at the Eisler Bros. Old Riverton Store (est. 1925) is the only appropriate way to finish this walk. Across the state line in Claremore, Oklahoma, we’ll pause at the Will Rogers Memorial Museum to reflect on the life of this beloved humorist.

Day 8: Edmond–Clinton, OK (B)

Oklahoma City “OKC” Walk, OK – 10 km, rated 1A

After a short stop at The Round Barn, one of many fun, quirky icons of Route 66, we continue into OKC, as the locals call it, for our Oklahoma City Walk. Featured along the trail are the seven-story, cylindrical Crystal Bridge at Myriad Botanical Gardens (admission not included) and the Oklahoma City National Memorial, eulogizing those lost in the tragic bombing of 1995.

Day 9: Clinton–Amarillo, TX (BD)

One of our favorite Route 66 museums is near our hotel in Clinton. After some time at this nostalgic window into the Oklahoma of yesteryear, America’s Main Street leads us into the Texas Panhandle. En route to Amarillo, the Devil’s Rope Museum (aka “barbed wire”) fills a surprisingly interesting gap in our knowledge of western lore. A memorable visit to a local cattle ranch this evening includes a fun cowboy dinner and introduces us to the larger-than-life legends of the Lone Star State.

Day 10: Amarillo–Santa Fe, NM (B)

Amarillo Panhandle Walk, TX – 10 km, rated 1A

Following a Texas-sized breakfast at the Big Texan Steak Ranch, our walk for the day explores the parks and neighborhoods along historic Route 66 in Amarillo. Continuing our westward pilgrimage, we’ll stop for a photo of the eclectic Cadillac Ranch then pay homage at the remains of Glenrio, a Route 66 ghost town straddling the Texas/New Mexico border. A brief stop in the Mother Road town of Tucumcari, an early supper at the Lake City Diner in Santa Rosa, and a scenic drive north to Santa Fe round out another classic day on the Road.

Day 11: Santa Fe–Albuquerque, NM (B)

Santa Fe Spanish Heritage Walk, NM – 10 km, rated 1A

The majority of today is devoted to a popular walk through New Mexico’s capital, the oldest town (established in 1610) west of the Mississippi. A captivating weave of Native American, Spanish, and Anglo cultures gives travelers insight into the heritage of New Mexico as they stroll past the capitol building, the original Palace of the Governors, and the 17th century San Miguel Mission Church.

Day 12: Albuquerque – Gallup, NM (B)

Albuquerque Balloon Fiesta Walk, NM – 10 km, rated 1A

Today’s Fiesta highlight is a Mass Ascension of all balloons, an event claimed to be the most photographed happening in the world! Following this hot air high, we’ll return to town for our walk through Old Town Albuquerque’s shops, galleries, and a stretch of Route 66. The Route from Albuquerque leads west towards Acoma Sky City Pueblo, a native community perched high atop a mesa since AD 1150 in an area of dramatic high-desert landscapes. Access to this oldest continuously inhabited community in North America is tightly controlled; we will visit in the company of a tribal member to learn the traditions and history of the tribe.

Day 13: Gallup – Flagstaff, AZ (B)

Flagstaff Route 66 Walk, AZ – 10 km, rated 2A

We’ll follow the open road westward into Arizona this morning, cruising past old Route 66 settlements like Holbrook before arriving at the Meteor Crater. At 4100 feet in diameter, this privately managed natural wonder is touted as the best-preserved meteorite crater on the planet! Continuing on, we arrive mid-afternoon for today’s walk in Flagstaff. Prior to its Route 66 days, this town’s “flagstaff” marked the trail for wagon trains bound for California.

Day 14: Flagstaff–Needles, CA (BL)

We leave Flagstaff today, returning to the Mother Road. Our mid-morning rest stop is in Seligman at the fabled Snow Cap Drive-In Restaurant, a Route 66 icon. One of the best preserved sections of the old road takes us to Kingman for a lunch stop, followed by the steepest portions of the Route that lead to the old mining town of Oatman, known for the semi-wild burros that wander the main street. We’ll overnight in Needles in preparation for tomorrow’s final run to the Pacific!

Day 15: Needles–Santa Monica, CA (B)

Hollywood Flats Walk, CA – 11/5 km, rated 1A

Beyond Needles, the dreaded heat of the Mohave Desert awaits, feared by drivers of less reliable, older vehicles more than any other stretch of Route 66. We’ll better understand their anxiety as we cruise the parched, unforgiving desert. We’ll stop for a lunch break and our last Route 66 Museum in Victorville before detouring off the Route for a walk along the star-studded streets of Hollywood.

Day 16: Activities in Santa Monica (BD)

Santa Monica End of the Route Walk, CA – 10 km, rated 1A

The Mother Road ends at the corner of Santa Monica Boulevard and Ocean Avenue in the popular ocean resort of Santa Monica, a stone’s throw from the waves of the Pacific. Our last walk features the Third Street Promenade, colorful Santa Monica Pier, and Palisades Park. You’ll have all day to explore “the end of the road”– consider a visit to one of Santa Monica’s many museums, enjoy the public murals and other monuments, or sample the shops and restaurants along the pier. Then join us for a Farewell Dinner tonight to reminisce about our memorable journey along the Mother Road!

Day 17: Return home from Santa Monica (B)

We’ll make our way to the Los Angeles International Airport this morning, saying farewell to our fellow pilgrims before returning to our own corners of America. As the old song goes, we “got our kicks on Route 66,” enjoying a nostalgic dose of the Mother Road and a slice of all things Americana along the way.

More Details

Click on each heading for more details.

How do I lock in my place on this Adventure?

Call or mail in your refundable Early Bird ($50) to save your spot! A maximum of 30 travelers will be accepted on this Adventure.

Early Bird deposits are refundable $50 deposits which serve to hold your spot on a tour until dates and pricing have been confirmed. Once all details on a tour have been finalized, travelers can then register with an additional $450 deposit to bring their total on a tour up to $500.

Traveler Rewards Program

New Travelers receive a $200 discount on the Historic Route 66 tour! Returning travelers receive our Alumni Traveler Discount of 5-10% off the main tour price. Terms, exclusions and conditions apply. See the Traveler Rewards page for more details or contact us with any questions at 800.779.0353 or [email protected].

How Is Airfare Arranged?

Travelers will fly into Chicago, IL at the start of this tour and fly out of Los Angeles, CA at the end of the trip. More details about flight arrangements and travel agent contact information will be made available after this tour has been finalized.

What about the walks?

We generally walk at a pace of 2 to 3 miles per hour. In most cases, we are not “strolling.” We are walking at a relaxed but steady pace. Your experience will be significantly affected by your level of physical fitness. If not walking regularly at home, we strongly recommend that you make a priority of “training” beforehand in order to both enjoy the trip and avoid medical issues due to overexertion. If you have questions about your ability to participate, please talk with our office at 1.800.779.0353.

We have adopted a walk difficulty rating system which contains a numeric indicator for trail incline and an alpha indicator for trail terrain. The explanation for this system is presented below:


1. Very small hills or very little stair climbing. Cumulative elevation gain from Starting Point: up to 200 feet.
2. Some moderate hills and stair climbing. Cumulative elevation gain from Starting Point: 200-1000 feet.
3. Some significant hill or stair climbing. Cumulative elevation gain from Starting Point: 1000-2000 feet.
4. Lots of significant hills or stair climbing. Cumulative elevation gain from Starting Point: 2000-3500 feet.
5. Many steep hills. Cumulative elevation gain from Starting Point: more than 3500 feet.


A. Almost entirely on pavement.
B. A significant part of the route is on well-groomed trails with very few obstacles.
C. A significant part of the route is on somewhat difficult terrain (rocky / rooted paths or soft sand).
D. A significant part of the route is on very difficult terrain.
E. The majority of the route is on very difficult terrain.

What happens next?

We are currently developing the itinerary for this Adventure. Once the itinerary is released, we will accept registration deposits ($500) to save space.

If you have Early Birded with a refundable $50 deposit, your spot on the tour will be held for 2 weeks after the itinerary is published while you make a decision on whether or not you’d like to register with an additional $450 deposit, bringing your total on the tour up to $500. If you decide not to join us for this tour, your Early Bird can be refunded or transferred to another tour.

We look forward to exploring “America’s Main Street” with you, experiencing a nostalgic slice of our shared American heritage. Start anticipating scintillating scenery, eye-opening excursions, wonderful walks, and an overall Apple Pie Americana Adventure as we walk Historic Route 66 in the fall of 2020!