Route 66 – Mother Road – Special 100 Year Anniversary Tour – 2026
Part 1: East (Chicago to Oklahoma City) – Mother Road in the Heartland
llinois, Missouri, Kansas, and Oklahoma
May 5 – 13, 2026 * (9 Days) – $3495
Part 2: West (Oklahoma City to Santa Monica) – Mother Road Out West
Oklahoma, Texas, New Mexico, Arizona, and California
May 12 – 23, 2026 * (12 Days) – $4675
Special 19-day Pilgrimage: The Heartland (Part 1) and The Out West (Part 2)
llinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California
May 5 – 23, 2026 * (19 Days) – $7666
*$504 discount for the combined 19 -day Tour
Adventure Pace
Tour Pace: 1 2 3 4 5
Walk Challenge: 1 2 3 4 5
Join Us for this Centennial Celebration
Spaces are limited and filling fast — registrations are confirmed in the order received.
Rediscover the soul of America on a once-in-a-century journey filled with classic cars, neon lights, small-town charm, and the timeless magic of the open road. Join us as we trace the Mother Road from Chicago to Santa Monica, connecting with the nostalgia of America’s coming of age as we wind our way through 8 states from Illinois to California!
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 an era when America moved at a slower and more connection-friendly pace.
The 2026 edition of Route 66 is the 100th anniversary of the opening of Route 66, and iconic Mother Road stops will be celebrated in diverse and colorful ways.
The tour can be done as a single 19-day pilgrimage (recommended) or parsed into either Part 1, The Heartland, or Part 2, The Out West.
TRIP DETAILS
PART 1
East (Chicago to Oklahoma City) – Mother Road in the Heartland
May 5 – 13, 2026 * (9 Days) * $3495
Including:
- 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 route (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 $689. We provide a roommate matching service for those interested.
Activities/Visits to:
- 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)
IMPORTANT INFO
Group Size
24 travelers maximum
Accommodations
Strategically located Tourist Class accommodations or better
Meals
All breakfasts. When possible, optional group meals may be offered. Letters BLD indicate which meals are included.
Airfare
Not included. Start point is our hotel in Chicago, served by Chicago O’Hare International Airport (ORD), Illinois. Finish point is Will Rogers International Airport (OKC), Oklahoma City, Oklahoma or continue to Part 2 (Pilgrimage Tour).
Transportation
Included. We use motorcoaches with a seating capacity of 40-55 seats.
Traveler Age
Our travelers usually range from 50–75 years of age. All ages welcome!
Itinerary
D1 – Tue, May 5: Arrival in Chicago
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
D2 – Wed, May 6: Chicago - Pontiac, IL (BD)
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 fun and historic little Route 66 town of Pontiac.
D3 – Thu, May 7: Pontiac, IL - Springfield, IL (B)
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.
D4 – Fri, May 8: Springfield, IL - St. Louis, MO (B)
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.
D5 – Sat, May 9: St. Louis, MO (B)
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 or 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 to explore the downtown area of St. Louis will be shuttled back to our hotel.
D6 – Sun, May 10: St. Louis, MO - Lebanon, MO (BD)
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 look forward to dinner with a local Ozark flavor.
D7 – Mon, May 11: Lebanon, MO - Miami, OK (B)
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 halfway along 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 sandwiches 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 hometown 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. Price to be communicated later and you will have an opportunity to sign up for this after you have registered for the tour.
D8 – Tue, May 12: Miami, OK - Oklahoma City, OK (B)
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, a 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.
D9 – Wed, May 13: Oklahoma City, OK – Home or continue to Part Two
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.
TRIP DETAILS
PART 2
West (Oklahoma City to Santa Monica) – Mother Road Out West
May 12 – 23, 2026 * (12 Days) * $4675
Including:
- All land travel as outlined in a 50+ seat motorcoach
- Tourist class or better hotel accommodations
- 14 meals: All breakfasts, 1 lunch, and 2 dinners as listed (BLD)
- 9 walk routes (plus optional walks in OKC on Day 1 and at Grand Canyon on Day 8)
- Walking fees for 6 walk stamps for those collecting AVA credit (if AVA sanctions approved)
- WAI guide service throughout (2 guides)
- All tipping for coach driver and group meal
- Pricing is based on double occupancy. A limited number of single rooms are available for a supplement of $990. We also provide a roommate matching service for those interested.
Activities/Visits to:
- Stafford Air & Space Museum – OK
- Oklahoma Route 66 Museum – OK
- Devil’s Rope Museum – TX
- Big Texan Steakhouse special dinner – TX
- Palo Duro Canyon State Park – TX
- Pecos National Historical Park – NM
- Santa Fe – NM
- Petrified Forest National Park – AZ
- Williams Route 66 town – AZ
- Grand Canyon National Park (optional)
- Seligman Route 66 town – AZ
- Arizona Route 66 Museum – AZ
- Countless Route 66 stops along the Mother Road
- Optional excursions:
- Pre-day activities in Oklahoma City (Day 1)
- Visit to Grand Canyon (Day 8)
IMPORTANT INFO
Group Size
24 travelers maximum
Accommodations
Strategically located Tourist Class accommodations or better
Meals
All breakfasts. When possible, optional group meals may be offered. Letters BLD indicate which meals are included.
Airfare
Not included. Start point is our hotel in Oklahoma City, served by Will Rogers International Airport (OKC), Oklahoma City, Oklahoma. Finish point is Los Angeles International Airport (LAX), Los Angeles, California.
Transportation
Included. We use motorcoaches with a seating capacity of 40-55 seats.
Traveler Age
Our travelers usually range from 50–75 years of age. All ages welcome!
Itinerary
D1 – Tue, May 12: Arrive Oklahoma City, Oklahoma
Optional Oklahoma City Capitol Walk – 10 km, rated 1A
This All-American Adventure begins near the geographic center of the USA in Oklahoma City. Travelers who arrive early are invited to participate in the self-guided Oklahoma City Capitol Walk, which can be started from our hotel, or consider other worthwhile points of interest within a short taxi ride.
Oklahoma City National Memorial Museum, a moving visit to come to terms with the horrific events of April 19, 1995, when a 4000-pound bomb was detonated in the heart of Oklahoma City, taking the lives of 168 people, and injuring four times that number. Estimated admission: $15 plus transportation. Timed entry must be booked in advance.
National Cowboy & Western Heritage Museum, located about a 15–20-minute taxi ride north of our hotel and one of the country’s premier repositories of American Western history, art, and culture. Estimated price: $15 plus transportation
Oklahoma State Capitol, for a fun and intriguing docent-led visit of the only capitol in the world with its own oil well on site.
A Welcome Orientation meeting this evening at our hotel gives us a chance to get acquainted and talk about adventures ahead on America’s Mother Road.
D2 – Wed, May 13: Oklahoma City, OK - Weatherford, OK (B)
Walk #1: Oklahoma City Bricktown Walk – 6 km, rated 1A
Walk #2: Bethany Route 66 Walk – 5 km, rated 1A
Today’s first walk features the Bricktown Canal walkway with the spectacular Centennial Land Run Monument – one of the world’s largest bronze statuaries with 45 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 (but not the museum), eulogizing those lost in the tragic bombing of 1995.
From OKC, we head west, picking up Route 66 and stopping in the town of Bethany to participate in one of the few trails where we walk directly on Route 66.
Following time for lunch, we continue west through other one-of-a-kind, small, western towns with links to the Mother Road en route to Stafford Air & Space Museum in Weatherford. This highly regarded Smithsonian-affiliated museum is named for Lt. General Thomas Stafford, legendary pilot and astronaut and a Weatherford native.
Our hotel is just a few minutes away in the bustling Route 66 town of Weatherford. We’ll offer an early and a later shuttle from the museum to our hotel and tempt you this evening with an optional Route 66 culinary experience at Lucille’s Roadhouse Diner.
D3 – Thu, May 14: Weatherford, OK - Canyon, TX (BD)
Several fun western towns and Route 66 stops are sprinkled along today’s route through western Oklahoma into Texas. Our first stop is just down the road a piece in Clinton. Here, the Oklahoma Route 66 Museum beckons us with an audio tour that winds through exhibits chronicling the sixty-plus years of American and Oklahoman history the Mother Road has witnessed.
Our first stop in the Lone Star State is the Devil’s Rope Museum (aka “barbed wire”). You may be surprised at the unexpected and intriguing gap in your knowledge of western lore closed by this stop!
Finally, a memorable dinner at the Big Texan Steakhouse makes good the boast that everything in Texas is big! Their 72-ounce steak is on the house, provided you can eat it in the space of 60 minutes.
We spend this evening in the small western town of Canyon, Texas
D4 – Fri, May 15: Canyon, TX - Las Vegas, NM (B)
Walk #3: Palo Duro Canyon Walk – 5 km, rated 1A
Just east of Canyon is the geological phenomenon for which the town is named.
The walk of the day is in Palo Duro Canyon, by some measures the second largest in the USA at roughly 120 miles long and six miles wide on average.
Continuing our westward pilgrimage, we stop for a photo of the eclectic Cadillac Ranch then enjoy a Route 66 no-host lunch at the halfway point on Route 66 between Chicago and Santa Monica.
A short and somewhat surreal stop offers a chance to pay homage at the remains of Glenrio, a true Route 66 ghost town straddling the Texas/New Mexico border.
Pausing briefly to stroll past a few Mother Road icons in the town of Tucumcari, we continue with a picturesque, high desert drive through New Mexico north to Las Vegas. This is not the town of casinos in Nevada; Las Vegas, New Mexico is a true western cowboy town settled in 1835 by ranchers who received a land grant from Mexico.
The Santa Fe Trail, Teddy Roosevelt Rough Rider gatherings, Cowboy Reunions, and a nasty reputation for outlaws and desperadoes are all part of Las Vegas lore; the town boasts more than 900 buildings on the state and National Register of Historic Places, including tonight’s hotel!
D5 – Sat, May 16: Las Vegas, NM - Santa Fe, NM (B)
Walk #4: Pecos Ancestral Trail – 2 km, rated 2B
Walk #5: Santa Fe Walk – 5/10/11 km, rated 1A
Leaving Las Vegas, we ascend over one of the most challenging sections of the earliest alignment of Old Route 66. New Mexico’s Glorieta Pass, winding between towering Sangre de Cristo Mountains and Glorieta Mesa at an elevation of 7500 feet above sea level, severely challenged primitive internal combustion engines of the 1920s and 1930s.
Today’s first stop is fascinating Pecos National Historical Park, set in the Pecos Valley, a path of least resistance through these mountains for thousands of years. Various Native America groups, Spanish conquistadors and missionaries, Mexican and Anglo armies, Santa Fe Trail followers, and travelers like us along Route 66 and later, Interstate 25, have all passed through the Pecos Valley.
The main attraction at Pecos National Historical Park is an introduction to the Pecos Pueblo with a short, scenic high altitude walk passing through ruins of the original circa 16th century settlement.
The afternoon and evening are devoted to a walk through fascinating and ever-popular Santa Fe, New Mexico’s capital established in 1610, ten years before the Pilgrims arrived at Plymouth Rock.
A captivating tapestry of Native American, Spanish, and Anglo cultures offers insight into the heritage of New Mexico as we stroll past the capitol building, the original Palace of the Governors, and the 17th century San Miguel Mission Church.
D6 – Sun, May 17: Santa Fe, NM - Gallup, NM (B)
Walk #6: El Morro National Monument – 5 km, rated 1A
In the 1930s, Route 66 was rerouted from the northern alignment in New Mexico to a southerly path through Albuquerque that involved less challenging elevation gains. Picturesque stretches of Route 66 across high desert landscape and through miniscule Mother Road communities take us to the town of Grants. Here, we take a break to pick up picnic supplies before leaving 66 to discover a different side of New Mexico’s charms.
The afternoon drive takes us through rugged, lava-ravaged landscapes, with multiple opportunities to get out and stretch our legs and experience remote New Mexico. We plan for our featured walk to be at El Morro, a small national monument in western New Mexico that protects a large sandstone bluff with a permanent pool of water at its base. For hundreds of years, travelers stopped here to rest and left more than 2,000 inscriptions and petroglyphs on the rock, alongside the remains of an Ancestral Puebloan village on top of the bluff.
Tonight, we lodge in iconic El Rancho Hotel, bursting with Route 66, Old West ambiance and frequent home to stars of yester-year like Kirk Douglas, John Wayne, Spencer Tracy, Ronald Reagan, and Katherine Hepburn.
D7 – Mon, May 18: Gallup, NM - Williams, AZ (B)
Walk #7: Petrified Forest National Park – 5 km, rated 2B (unsanctioned)
We follow the open road westward into Arizona this morning. Our first activity today is a series of short trails highlighting the diversity of Petrified Forest National Park, where beautifully marbled chunks of petrified wood lie strewn around the desert like a discarded game of oversized, prehistoric, pick-up sticks.
Other park highlights include Native American petroglyphs, the multi-hued badlands Painted Desert, and even crossing an overgrown section of Old Route 66.
We were pleasantly surprised by Williams, Arizona and consider it our favorite Route 66 town! We stay here two nights, using it as a base to explore the Grand Canyon!
D8 – Tue, May 19: Activities in Williams, AZ (B)
Optional Grand Canyon South Rim Walk – 5/10 KM, rated 3B — elevation-7000’
Today is a free day. Our hotel is just a few minutes walk from shops, restaurants, and diners of Route 66; browsing, window-shopping, and snacking are a great way to enjoy the Route 66 ambiance and relax after a busy week along Route 66.
Optional Grand Canyon Excursion: For those who’d like to keep moving and see one of the wonders of the world, the Grand Canyon is within reach on a memorable day trip.
Due to challenging group restrictions in the Park, WAI is not able to arrange a group visit. However, a vintage railroad trip is a fun and easy way to see the Canyon from Williams.
Grand Canyon Railway charges about $100 per person round-trip in coach class. The train departs at 9:30 am (train station walkable from our hotel) and arrives at the Canyon at 11:45 am. You then return on 3:30 pm train, getting back before 6 pm.
WAI will send information to help you book train tickets in the Adventure Advice memo that comes a bit later in the process.
Canyon-goers should be back in Williams in time to enjoy a fun dinner along Route 66.
D9 – Wed, May 20: Williams, AZ - Needles, CA (B)
We leave Williams today, returning to Route 66 to travel the best-preserved section of the Mother Road.
Our midmorning stop in Seligman offers a colorful handful of Route 66 diners and gift shops, including the fabled Snow Cap Drive-In Restaurant, a Route 66 icon started by Juan Delgadillo. Juan’s brother, Angel, is widely considered the “Father of the Mother Road” for successfully petitioning for “Historic Route 66” signage and designation for the Road in Arizona, a 1980s movement that carried to the other seven states.
We continue along 66 from Seligman to Kingman for a no-host diner lunch and a visit to an excellent Route 66 museum. The last Route 66 stop of the day is the old mining village of Oatman, known for semi-wild burros that wander main street panhandling for donkey food sold by local vendors to be handed out by visitors.
Our lodgings for the night are across the border in Needles, California, jumping off point for tomorrow’s final run to the Pacific!
D10 – Thu, May 21: Needles, CA - Marina del Rey, CA (BL)
Walk #8: Beverly Hills Walk – 6 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 better understand this anxiety as we cruise the parched and unforgiving but often picturesque desert.
Entering the more populated areas of Southern California, lunch today is a stop for burgers and fries at a quintessential SoCal culinary institution, an In-N-Out burger joint.
A final range of mountains is our final barrier for reaching the coast and our objective in Beverly Hills. A walk here takes us through two famous segments – homes of the rich and famous and Rodeo Drive, the ultra-posh shopping district where seeing and being seen is more important than what you buy.
We end the day in a lovely hotel in Marina del Rey in anticipation of finishing Route 66 in style tomorrow!
D11 – Fri, May 22: Activities in Marina del Rey, CA (BD)
Walk #10: Santa Monica End of the Road Walk – 8/11 km, rated 1A
The Mother Road ends at the corner of Santa Monica Boulevard and Ocean Avenue, a stone’s throw from the waves of the Pacific in the popular ocean resort town of Santa Monica.
The final walk starts from our hotel in Marina del Rey and winds through upscale neighborhoods and along the canals of Venice to the beach. A stretch along the Ocean Front Walk – a lengthy and colorful seaside promenade that includes Venice Beach Boardwalk, Venice Muscle Beach, and several parks, finishes at the Santa Monica Pier, right next to the end of Route 66 on Ocean Avenue.
You have all day to enjoy this walk and explore “end of the road” attractions such as one of Santa Monica’s many museums, public murals and monuments along the walk, shops and restaurants along the pier, a Venice Beach food tour for lunch, or any of a host of bike, Segway, or bus tours offered in the Santa Monica/Los Angeles area.
Join us this evening for a fun and relaxing Farewell Dinner to reminisce about our memorable odyssey along the Mother Road!
D12 – Sat, May 23: Santa Monica, CA – Home (B)
Make your way to nearby Los Angeles International Airport this morning, bidding farewell to fellow Route 66 Roadies before returning to your own corner of America. As the song says, we “got our kicks on Route 66.”
We connected with our country on a road less traveled down the Main Street of America. We took a road obstructed by traffic signals and stop signs that made us slow down, a road representing a time when relationships trumped efficiency. Thanks for sharing this nostalgic mother of all road trips along the Mother Road.
BEFORE YOU BOOK
How Do I Lock in My Place on This Adventure?
To register, a non-refundable $500 deposit is required to hold your spot. If you’ve already pre-registered for this tour ($200), all that is required is an additional $300 to lock in your place.
A second non-refundable $500 deposit is due by January 6, 2026. Final payment is due 90 days before departure and is non-refundable after the due date. You will receive a prompt email from us 2 to 3 weeks in advance of each payment deadline.
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
What is a Classic Curated Tour?
With help from local experts and walking guides, these itineraries are crafted with extensive on-site planning by WAI tour planners.
When designing 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 also touch, smell, and feel these special spaces.
Along the way, interactions with locals amplify the experience by sharing insights into the magic of that particular location.
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!
Walk Ratings
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 in order 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 office@walkingadventures.fun
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:
INCLINE
- Minimal hills or stair climbing. Cumulative elevation gain: <200 feet.
- Some moderate hills and stair climbing. Cumulative elevation gain: 200-1000 feet.
- Some significant hill or stair climbing. Cumulative elevation gain: 1000-2000 feet.
TERRAIN
- Almost entirely on pavement.
- A significant part of the route is on well-groomed trails with very few obstacles.
- A significant part of the route is on somewhat difficult terrain (rocky / rooted paths or soft sand).
Walk Difficulty
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 above).
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.
Tour Accommodations
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 heritage hotel reflecting the spirit of Historic Route 66, which we think you’ll enjoy.
Accommodations on this adventure are single-floor or have elevators.
How Is Airfare Arranged?
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.
The official start point for Route 66 ~ Part 2: Mother Road Out West 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.
The official finish point for Part 2 is our hotel in Marina del Rey, California. The logical airport to use is Los Angeles International Airport (airport code LAX), about 15 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!
Laura Pfahler: 503.434.6401 or llp@wtpdx.com
Travel Insurance
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. Many travel insurance providers are available for you to consider.
Laura Pfahler and Sharon Mitchell of World Travel Inc. are travel agents who provides air travel and insurance services to many WAI travelers.
Laura Pfahler: 503-434-6401 or llp@wtpdx.com
Sharon Mitchell: 971-261-2091 or smitchell@wtpdx.com
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.).
Be aware that some travel insurance policies contain time-sensitive provisions (i.e. some benefits, such as coverage of pre-existing conditions, are available only if the policy is purchased within a certain number of days of the purchase of the travel package). In addition, remember that airfare is not covered by any travel insurance policy you may have purchased for the tour.
As always, do some shopping to ensure you are getting the best value. Using
the SquareMouth.com website can be a good way to compare pricing.
Other options include:
- Allianz
- Betins
- Travel Guard
- Travel Insured International
WAI bears no responsibility for travel insurance benefits advertised by various credit card companies. If you are relying on this type of benefit for insurance, we advise you to verify coverage types and limits and that your purchase does in fact qualify you for this insurance.
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.
What if WAI Cancels the Tour
Walking Adventures International reserves the right to cancel this tour departure with fewer than 15 participants, in which case registered participants will receive a 100% refund of payments received.
This refund policy contains one exclusion. Many suppliers require non-refundable deposits as a condition of booking services. Though it is rare, unforeseen circumstances can force us to cancel a tour. In cases where supplier’s non-refundable policies are imposed, 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.
Wellness Policies for This Tour
Our approach to wellness on tour has traditionally been to encourage travelers to:
- Focus on health before the tour so you start healthy.
- Pace yourself while on tour; travel is inherently stimulating and can produce adrenalin boosts that mask energy drain. Guard your energy reserves and consider the length of the trip and whether to opt out of some activities and/or walks.
- Be self-aware. If you feel yourself tiring or feel a bug coming on, take precautions to block it (e.g. extra rest, extra doses of vitamin C, etc).
- If you feel a bug coming on or if you take ill, distance yourself from others when possible.
- If you feel ill, isolate yourself towards the back of the bus and away from others and please wear a mask.
What Happens Next?
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 second non-refundable deposit of $500 is due by January 6, 2026.
A final payment is due 90 days before departure (early to mid-February, 2026) and is non-refundable after the due date. You will receive a prompt email from us a week or two in advance of each payment deadline. 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 Route 66 – Mother Road 100 Year Anniversary Tour itinerary. We are eager to share this unique slice of Americana in the springtime with you!