Route 66 ~ The Mother Road

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

WAI is thrilled to offer a repeat performance of a historic and nostalgic walking tour along our nation’s premier heritage highway—Route 66!

Route 66 ~ Part 1: Mother Road in the Heartland

September 25 – October 3, 2023 * 9 Days * $2590

Illinois, Missouri, Kansas, and Oklahoma

Part 1: Mother Road in the Heartland begins in Chicago, ends in Oklahoma City, and explores Route 66 for 9 days  in Illinois, Missouri, Kansas, and Oklahoma.

Route 66 ~ Part 2: Mother Road Out West

Oklahoma, Texas, New Mexico, Arizona, and California

Part 2: Mother Road Out West overlaps with Part 1 in Oklahoma City and ushers the traveler into the wide-open spaces of the American Southwest on a longer, 12-day adventure in Oklahoma, Texas, New Mexico, Arizona, and California.

Historic Route 66 Illinois Pontiac (3)

Join us as we trace the Mother Road from Chicago to Oklahoma City, connecting with the nostalgia of America’s coming of age as we wind our way through 4 states from Illinois to Oklahoma!

The theme of this trip goes much deeper than a 19-day road trip from Chicago to Santa Monica, California. Truly, it’s a connection with America, the way America was and the way America still is and can be.

This experience peels back digital layers of 21st century America and helps us rediscover our analog past. Route 66 represents a time when travelers drove through small towns instead of around them on freeways, when stoplights and 2-lane roads slowed the pace of travel enough for people to smile at one another and stop for a meal or a motel room.

This is a search for the soul of America, and, as always, walking is the best way to discover what is true and real and tangible. Walking is the ultimate way to slow down a journey that is all about a era when America moved at a slower and more connection-friendly pace.


Route 66 ~ Part 1:
Mother Road in the Heartland


  • All land travel as outlined
  • Tourist class or better hotel accommodations
  • 10 meals: 8 breakfasts and 2 dinners as listed (BD)
  • 7 walk routes
  • Fees for 6 walk stamps for those collecting AVA credit
  • 1 additional optional walk routes (Day 5)
  • WAI guide service throughout
  • Cultural and historical expertise of local guides at select points of interest
  • All tipping for coach driver, local guides, and group meals
  • Pricing is based on double occupancy. A limited number of single rooms are available for a supplement of $595. We provide a roommate matching service for those interested.

Visits to/Activities:

  • Chicago Architecture Cruise
  • Pontiac Museum Complex & trolley
  • Abraham Lincoln Museum
  • Lincoln Tomb
  • Ted Drewes Frozen Custard
  • Baxter Springs Heritage Museum
  • Will Rogers Memorial Museum
  • Route 66 Interpretive Center – Chandler, OK
  • Oklahoma state capitol tour
  • Countless Route 66 stops along the Mother Road

Optional Activities:

  • Dinner and tour at Coleman Theater in Miami, Oklahoma (Day 7).
  • Oklahoma City National Memorial (Day 9)
Route 66 Map

Adventure Pace

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

About Adventure Pace

Important Info

Your Guides

Tim Friesen

Tim has been guiding for Walking Adventures since 2003, most often leading our summertime adventures in Europe. Throughout the school year, Tim has had a long career as a high school music teacher in Molalla, Oregon, and is occasionally known to burst into song on the trail!

In 2019, Tim worked with brother Dan Friesen, WAI owner, on a 3-week long project to review and update our Route 66 journey of nostalgia,  scouting out the best haunts and venues for this historic highway linking Chicago to Santa Monica. Along the way, Tim was taken with this indelible part of America’s past and looks forward to sharing America’s Route 66 with you!

Jim Brickley

Jim has always loved a good adventure and the opportunity to explore. Now retired, Jim served for over 30 years as an Advanced Math teacher for high schoolers. He has been married for over 30 years to his wife Kathy and has 2 grown sons. Jim enjoys interacting in various environments with different cultures, and welcomes the challenges travel brings. His hobbies include motorcycling and scuba diving, as well as hiking and travel. He anticipates growing through diverse travel encounters that challenge his paradigm of “normal” and looks forward to sharing these learning experiences with you on tour.


Click on each day to reveal more details. BLD refers to meals included, Breakfast, Lunch or Dinner.

Our Adventure along Route 66, referred to by John Steinbeck as “the Mother Road” and “America’s Main Street,” begins today in the Windy City of Chicago! Travelers can anticipate a deep connection with the heartland of America along the entire 2,448-mile route in all eight states including Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.

Because travelers arrive throughout the day, the first official group activity is our Welcome Orientation this evening at our strategically located hotel, across from Grant Park and Buckingham Fountain, on the shores of Lake Michigan.

Chicago Lake Michigan & Windy City Walk – 9 km, rated 1A

Today starts with breakfast at Lou Mitchell’s Restaurant, a Chicago institution since 1923 and a fixture at the beginning (or end) of Route 66 since the road opened in 1926.

Our morning walk passes Windy City classics like the Shedd Aquarium, the Field Museum, and a long, lovely stretch along Lake Michigan through Lakefront Park, past the Chicago Yacht Club, through Lake View Park, and across the Chicago River to Navy Pier.

After free time for lunch, we board a riverboat for the justly renowned architectural cruise up the Chicago River. Excellent commentary unlocks a vast store of intriguing Chicagoan history and more architectural wonders per square foot of riverfront than we’ve seen anywhere!

By mid-afternoon, our 2,400+ mile pilgrimage to Santa Monica, California begins. After a bit of freeway, we pick up the Mother Road as it snakes through small towns and farmland to our in the fun and historic little Route 66 town of Pontiac.

Pontiac is a delightful Route 66 stop with a surprising batch of museums and friendly locals proud to share their town. A trolley ride winds past a delightful array of murals and points out connections to attorney Abraham Lincoln in his pre-presidential days.

The Pontiac Museum Complex is a trove of local lore, including a floor dedicated to Route 66, an astonishingly detailed tribute to armed services members from Livingstone County, and several other high-quality exhibits.

Today’s no-host lunch is at Dixie Café, laying claim as the country’s oldest truck stop.

Not far down the road, the afternoon is reserved for the outstanding Abraham Lincoln Museum, with multiple exhibits and films paying tribute to the life and times of our 16th president who guided us through what many historians consider to be America’s most trying era.

Abe Lincoln Springfield Capitol Walk – 6 km, rated 1A
Chain of Rock Bridge Walk – 2 km, rated 1A

Our Springfield walk traces the heritage of Abraham Lincoln, passing the state capitol, the Governor’s Mansion, and the Lincoln Home (a national park site).

After paying tribute at the Lincoln Tomb, we enjoy a no-host Route 66 lunch at Cozy Dog Drive-In, which lays claim as creator of the corn dog concept forever linked with state and county fairs.

Following the Mother Road (interposed with some sections of freeway), we continue south through pleasant rural scenes. Our method of crossing the Missouri border involves walking above the Mississippi River across the pedestrianized Chain of Rock Bridge, also notable for its 30-degree bend halfway across the bridge.

We look forward to a two-night stay in St. Louis, widely considered to be the gateway of westward expansion following the US purchase of the vast Louisiana Territory from Napoleon of France in 1803.

St. Louis Amazing Arch Walk – 5/10 km, rated 1A
Forest Park Walk – 10 km, rated 1A (optional)

Starting and finishing from our hotel, today’s walk encompasses many of the highlights of St. Louis, including the Jefferson National Expansion Memorial (free admission) anchored by the famous Gateway Arch, largest monument in the USA–larger than the Statue of Liberty of the Washington Monument (admission not included)!

Other highlights of this outstanding introduction to St. Louis include St. Louis City Hall (a near-perfect replica of Paris’ Hotel de Ville), the Renaissance Grand Hotel (the first hotel in the country to feature air conditioning), the Old Courthouse (where slave auctions were held until abolitionists blocked them in 1861), Busch Stadium (home of the St. Louis Cardinals), and newly renovated Union Station.

Early this afternoon, join us for an excursion to Ted Drewes, purveyor of delicious frozen custard desserts and a Route 66 icon since 1929.

From Ted Drewes, walkers interested in today’s second walk or travelers who’d like to do more exploring will be dropped off at Forest Park. Larger than New York’s Central Park, Forest Park was opened in 1876, hosted both the 1904 World’s Fair and 1904 Summer Olympics, and boasts a bevy of top-notch points of interest like Saint Louis Zoo, Missouri History Museum, Saint Louis Science Center, Saint Louis Art Museum, the Jewel Box greenhouse, and much, much more.  The entire walk takes place inside phenomenal, expansive Forest Park. Admission is free to all the sites within Forest Park.

Travelers who prefer the afternoon off will be shuttled back to our hotel.

Cuba Mural Walk – 6 km, rated 1A

Route 66 leads diagonally across Missouri all the way to Cuba…Missouri, that is!

This friendly Route 66 town welcomes us with a creative collection of murals and picturesque, small-town Ozark neighborhoods, and a fun no-host barbecue lunch at the walk finish in a state well known for outstanding barbecue.

Several quirky, nostalgic Route 66 stops dot our afternoon drive through the Ozarks to Lebanon where we overnight in one of the few remaining Mother Road motels. Posh accommodations are not the goal tonight, but we think you’ll be comfortable. We look forward to dinner with a local Ozark flavor this evening to complement tonight’s informal Route 66 lodgings.

Baxter Springs Walk (KS) – 6 km, rated 1A

We start our day with a classic Route 66 stop, oozing with more classic Old Road character, on the western edge of Missouri before crossing into Kansas.

The state of Kansas lays claim to only 13 miles of the Route. About half way our Kansas journey, one of our favorite Route 66 stops is at Nelson’s Old Riverton Store (est. 1925) where a batch of pre-ordered deli sandwich await us for a no-host lunch.

This surprising little corner of Kansas offers more than its share of historical drama, including the 1863 Battle of Baxter Springs between Quantrill’s Raiders and Union forces. Our Kansas walk features Baxter Springs and finishes at the excellent Baxter Springs Heritage Museum, one of the better small-town museums we’ve seen.

Crossing into Oklahoma, we pass through Mickey Mantle’s home town of Commerce en route to the small Route 66 town of Miami (pronounced “my-am-uh”).

After a full day along the Route, an optional dinner is offered this evening at Miami’s Coleman Theater, 1929 contemporary of Route 66 designed with an elaborate Mission Revival exterior and a stunning Louis XV interior. A tour of this classic theater is included after dinner. Estimated price: $50 per person.

In 1952, the U.S. Highway 66 Association dubbed Route 66 “Will Rogers Highway”. We learn why when we arrive in Claremore this morning to visit the Will Rogers Memorial Museum and reflect on the life of this beloved humorist, trick roper, actor, newspaper columnist, and social commentator.

Just south of Claremore is the Blue Whale, an quirky, obligatory stop for any serious Route 66 traveler!

The Route 66 Interpretive Center in Chandler offers a fun set of films (viewed from the bench seats of classic cars) and exhibits about the Route.

Oklahoma has more drivable miles of Route 66 (over 400) than any other state! We cover a good percentage of those today, with more fun or historic points of interest punctuating our drive into Oklahoma City, where we spend the night in Bricktown.

Oklahoma City Walk – 6/10 km, rated 1A

Our Oklahoma City Walk features the Bricktown Canal walkway with the spectacular Centennial Land Run Monument–one of the world’s largest with 45 bronze figures frozen in time during the dramatic Land Run of 1889. Also along the trail are the seven-story, cylindrical Crystal Bridge at Myriad Botanical Gardens and the evocative Oklahoma City National Memorial, eulogizing those lost in the tragic bombing of 1995. Time is allowed to visit the memorial museum (admission not included) before we drive to the state capitol for a docent-led visit of the only capitol in the world with its own oil well on site.

NOTE: Travelers who opt for today’s 10 km walk route will use the local club’s self-guided directions and walk by the capitol but would not be with the group for the guided tour.

Travelers finishing their Route 66 experience with us in Oklahoma City should plan on a mid to late afternoon flight departure to participate in this morning’s OKC walk.

Thank you for joining us for Route 66 ~ Part 1: Mother Road in the Heartland.

Before You Book

Click on each heading for more details. More information will be provided at the time of registration.

To register, a non-refundable $300 deposit is required to hold your spot. A final payment is due 90 days before departure and is non-refundable after the due date. You will receive a prompt email from us a week or two in advance.

Soon after registration, an “Adventure Advice” email will be sent with critical information on flight arrangements as well as important steps to take in the months before your trip. Please do not buy your airline tickets until you review this Adventure Advice email.

Please follow this link to read our full General Tour Conditions.

Route 66 vs. Freeway Miles

Route 66 was first opened in 1926. It began to change almost immediately as planners and engineers looked for more efficient ways for automobile traffic to traverse the space between Chicago and Santa Monica. As a result, there are often multiple iterations or “alignments” of the road according to when they were used. In many cases, the road was covered by subsequent freeway construction.

We will not be on Route 66 for the entire 2,448 miles of the original road. That is no longer possible because of the covering of the road by freeway in some cases and by the impassable condition of the road in other places. We will, however, travel significant sections of Route 66, and our planners have selected what we believe are the most interesting sections of the road to share, those that reflect the spirit of Route 66.

We intentionally avoid long sections of freeway frontage road that are labeled “Route 66” but simply run adjacent to the freeway and offer little interest or value. Instead, we are in search of sections of the route that take us through the countryside of America and through the small towns whose fortunes ebbed and flowed with the pulse of traffic along Route 66. It’s an epic journey, and we hope you can join us!

With help from local experts and walking guides, these itineraries are hand-crafted with extensive on-site planning by WAI tour planners.

When planning Classic Curated Tours, our objective is to capture the essence of a destination–the history, culture, and natural wonders unique to that part of the world. We then build activities and walks that take us inside these characteristics.

Yes, these tours are educational, but they are also interactive and immersive; walking gets us off the bus and penetrates local cultures to not only see, but touch, smell, and feel these special spaces.

Along the way, interactions with locals amplify the experience as they share insights into the magic of that particular location.

Walks on this tour are a combination of trails planned in partnership with local walking clubs and vetted by our WAI guide team or planned on site by WAI tour planners.

As a group, this is an easy collection of trails, most rated as 1A, the easiest category in our rating system (see Walk Ratings below).

Because we are on Route 66, many of these trails explore towns and cities along the Route, and are therefore on sidewalks and hard surfaces rather than natural trails.

We generally walk at a pace of 2 to 3 miles per hour. Several walks on this trip are oriented more towards education, and therefore take longer due to stops for guide commentary. Nature walks, on the other hand, generally continue at a steadier pace because we’re stopping less to talk.

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 to both enjoy the trip and avoid medical issues due to overexertion. If you have questions about your ability to participate, please contact our office at [email protected].

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 on the table below:


1. Minimal hills or stair climbing. Cumulative elevation gain: <200 feet.
2. Some moderate hills and stair climbing. Cumulative elevation gain: 200-1000 feet.
3. Some significant hill or stair climbing. Cumulative elevation gain: 1000-2000 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).

Good quality, tourist-class accommodations are the standard for our Adventure. Most accommodations on this tour are selected primarily as a practical base from which to pursue our itinerary.

Because much of this Adventure is in small towns, a few of our properties are quality motels reflecting the spirit of Historic Route 66, which we think you’ll enjoy.

Most, but not all, of our accommodations on this adventure are single-floor or have elevators. Travelers should be able to carry their luggage up a number of steps to get to a second-floor room if necessary.

The official start point for Route 66 ~ Part 1: Mother Road in the Heartland is our hotel in Chicago, Illinois. The nearest airports are Chicago O’Hare International Airport (airport code ORD) which is about 60 minutes from our hotel, and Chicago Midway International Airport (airport code MDW) which is about 30 minutes from our hotel.

The official finish point for Part 1 is our hotel in Oklahoma City, Oklahoma. The logical airport to use is the Will Rogers World Airport (airport code OKC), about 20 minutes from our hotel.

We recommend that you contact Laura Pfahler, the travel agent we work with, to help book your flight arrangements. In this age of airfare complications and airport uncertainty, using a travel agent is a good investment! More details about flight arrangements and travel agent contact information will be provided in an Adventure Advice PDF by email after you register for the Adventure.  Please do not book your airfare prior to receiving these flight details from us!


WAI believes strongly in the importance of travel insurance for financial and medical protection from any number of unforeseen circumstances that can arise before departure or during your Adventure. This is now especially true in the era of COVID-19, which is typically treated like any other illness for travel insurance purposes. Many travel insurance providers are available for you to consider. Laura Pfahler and Sharon Mitchell of World Travel Inc. are travel agents who provide air travel and insurance services to many WAI travelers.

Laura Pfahler: 503.434.6401 or [email protected]

Sharon Mitchell: 971.261.2091 or [email protected]

Check out Insurance Tips from World Travel for a short introduction to travel insurance. (NOTE: WAI receives no commission or financial remuneration from World Travel Inc.).

As always, do some shopping to ensure you are getting the best value. Using the website can be a good way to compare pricing.

Other options include:

Travel Guard
Travel Insured International

NOTE: We suggest purchasing from a reputable, well-established insurance company (avoid buying insurance from an unknown company found only online). Travelers interested in purchasing “cancel for any reason” insurance coverage should be careful to check pricing and terms BEFORE they register for a tour. Recent changes in the international travel landscape has caused changes in the policies of some insurance companies, and made the purchase of this particular type of policy even more time-sensitive.

Walking Adventures International reserves the right to cancel this tour departure with fewer than 12 participants, in which case registered participants will receive a 100% refund of payments received.

This refund policy contains one exclusion. Some suppliers require non-refundable deposits as a condition of booking services. Unforeseen circumstances can, in rare circumstances, force us to cancel a tour. Due to these supplier’s non-refundable policies, WAI attempts to retrieve as much of these deposits as possible, but cannot guarantee a 100% refund. In cases where full refunds cannot be obtained for a cancelled tour, we will do our best to transfer unrefunded money as traveler credits to be applied to a future tour to that destination.

WAI has relaxed our policies and currently require no mitigation procedures (current WAI Wellness on Tour Policy). However, Walking Adventures International policy includes endeavoring to comply with any COVID-19 policies in place in the destinations through which we travel.

We are not aware of any COVID-19 policies or restrictions that will impact this tour along Route 66.

WAI will update travelers upon learning of any changes.

Travelers participating in the Route 66 ~ The Mother Road tour must agree to abide by policies in place at the time of travel.

Upon registering for this Adventure, you will receive a welcome email and initial invoice notifying you of your tour balance and due date. All payments for the tour or optional services/excursions can now be made online.

Soon after registration, an “Adventure Advice” email will be sent with critical information on flight arrangements as well as important steps to take in the months before your trip. Please do not buy your airline tickets until you review this Adventure Advice email.

A final payment is due 90 days before departure (currently June 27, 2023) and is non-refundable after the due date. You will receive a prompt email from us a week or two in advance. Please see our General Tour Conditions for the full terms and conditions for participation in this Adventure.

Around 2-3 weeks before departure, you will receive a final email packet with details of the program, including hotel names and contact information, a list of fellow travelers, and a more detailed daily schedule.

Take a few minutes to peruse the enclosed itinerary. In the end, we think you will agree that walking is still and always the best way to experience our world. Join us for this nostalgic Walking Adventure program through Route 66—The Mother Road!

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Route 66 ~ The Mother Road 2023