Route 66 Part 1

The Mother Road turns 100 in 2026, and there's never been a better time to walk the stretch that started it all. Part 1 follows Route 66 from its origin at the Art Institute of Chicago through the heartland of Illinois, across the Mississippi into Missouri, and down through the Ozarks to Oklahoma City. Along the way, you'll walk in the footsteps of Abraham Lincoln in Springfield, taste Ted Drewes frozen custard in St. Louis, cruise past vintage motels and classic diners, and feel the open road under your feet in a way that no car window could ever deliver.

📄Want the full picture? Download our brochure with the complete day-by-day itinerary, pricing, and trip details.

Day-by-Day Itinerary

Walk Rating Key

Incline

Gentle — gain < 200 ft

Moderate — gain 200–1,000 ft

Steep — gain 1,000–2,000 ft

Terrain

🏙️ PavedAlmost entirely on pavement

🥾 TrailsWell-groomed trails, few obstacles

⛰️ RuggedRocky, rooted paths, or soft sand

Day 1

Arrive Chicago · Welcome Orientation

▾

Our adventure along Route 66 begins in the Windy City of Chicago. Travelers arrive throughout the day to our hotel across from Grant Park and Buckingham Fountain on the shores of Lake Michigan. The first official group activity is our Welcome Orientation this evening.

Day 2

Chicago to Pontiac · Lake Michigan Walk · Architecture Cruise

1 walk · 9 km

▾

Breakfast at Lou Mitchell's, a Chicago institution since 1923 and a Route 66 fixture since the road opened in 1926. Our morning walk passes the Shedd Aquarium, Field Museum, and a long stretch along Lake Michigan to Navy Pier (9 km, rated 1A). After lunch, we board a riverboat for the renowned architectural cruise up the Chicago River. By mid-afternoon, our 2,400-mile pilgrimage to Santa Monica begins as we pick up the Mother Road through small towns and farmland to Pontiac.

Chicago Lakefront Walk9 km🏙️ Paved

Day 3

Pontiac to Springfield · Pontiac Museums · Abraham Lincoln Museum

▾

Pontiac is a delightful Route 66 stop with a surprising collection of museums. A trolley ride winds past murals and 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. Lunch at Dixie Café, claiming to be the country's oldest truck stop. The afternoon is reserved for the outstanding Abraham Lincoln Museum.

Day 4

Springfield to St. Louis · Lincoln Heritage Walk · Chain of Rock Bridge

2 walks · 8 km

▾

Our Springfield walk traces the heritage of Abraham Lincoln, passing the state capitol, Governor's Mansion, and the Lincoln Home (6 km, rated 1A). After the Lincoln Tomb, we lunch at Cozy Dog Drive-In, claiming to have created the corn dog. We cross the Missouri border by walking above the Mississippi River on the pedestrianized Chain of Rock Bridge (2 km, rated 1A), notable for its 30-degree bend. Two-night stay in St. Louis, gateway of westward expansion.

Springfield Lincoln Heritage Walk6 km🏙️ Paved

Chain of Rocks Bridge Walk2 km🏙️ Paved

Day 5

St. Louis · Gateway Arch Walk · Forest Park

3 walks · 25 km

▾

Today's walk encompasses St. Louis highlights including the Gateway Arch, the largest monument in the USA (5/10 km, rated 1A). Highlights include City Hall, the Old Courthouse, Busch Stadium, and Union Station. Afternoon excursion to Ted Drewes frozen custard, a Route 66 icon since 1929. Optional second walk through Forest Park (10 km, rated 1A), larger than Central Park, home to the 1904 World's Fair, with free-admission museums and gardens.

St. Louis Gateway Arch Walk5 km🏙️ Paved

St. Louis Gateway Arch Walk (extended) (alternative)10 km🏙️ Paved

Forest Park Walk (optional) (alternative)10 km🏙️ Paved

Day 6

St. Louis to Lebanon · Cuba Mural Walk · Ozark Country

1 walk · 6 km

▾

Route 66 leads diagonally across Missouri to Cuba — Missouri, that is. This friendly town welcomes us with a creative collection of murals and picturesque small-town Ozark neighborhoods (6 km, rated 1A). Quirky, nostalgic Route 66 stops dot our afternoon drive through the Ozarks to Lebanon, where we enjoy dinner with a local Ozark flavor.

Cuba Mural Walk6 km🏙️ Paved

Day 7

Lebanon to Miami · Kansas · Baxter Springs Walk · Coleman Theater

1 walk · 6 km

▾

Classic Route 66 stops on the western edge of Missouri before crossing into Kansas, which claims only 13 miles of the Route. Lunch at Nelson's Old Riverton Store (est. 1925). Our walk features Baxter Springs and finishes at the excellent Heritage Museum (6 km, rated 1A). Crossing into Oklahoma through Mickey Mantle's hometown of Commerce to Miami. Optional dinner at the 1929 Coleman Theater with its stunning Louis XV interior.

Baxter Springs Heritage Walk6 km🏙️ Paved

Day 8

Miami to Oklahoma City · Will Rogers · Blue Whale · Route 66 Interpretive Center

▾

We visit the Will Rogers Memorial Museum in Claremore and reflect on the life of this beloved humorist and social commentator. Just south is the Blue Whale, a quirky obligatory stop for any serious Route 66 traveler. The Route 66 Interpretive Center in Chandler offers films viewed from bench seats of classic cars. Oklahoma has more drivable miles of Route 66 than any other state — over 400. We spend the night in Oklahoma City's Bricktown district.

Day 9

Oklahoma City Walk · Capitol Tour · Depart or Continue to Part 2

2 walks · 16 km

▾

Our Oklahoma City Walk features the Bricktown Canal walkway with the spectacular Centennial Land Run Monument — one of the world's largest bronze statuaries with 45 figures (6/10 km, rated 1A). Also along the trail: Crystal Bridge at Myriad Botanical Gardens and the Oklahoma City National Memorial. We visit the state Capitol, the only one in the world with its own oil well. Travelers depart OKC or continue to Part 2.

Oklahoma City Bricktown Walk6 km🏙️ Paved

Oklahoma City Bricktown Walk (extended) (alternative)10 km🏙️ Paved

Take this itinerary with you.

Download the full brochure with day-by-day details, pricing, and what's included.

What's Included

Included

All land travel by motorcoach
hotel accommodations
8 breakfasts
4 group dinners
7 guided walks
Route 66 museum admissions
Abraham Lincoln sites
WAI guide service throughout. Based on double occupancy.

Not Included

Airfare
lunches
most dinners
travel insurance
single supplement
personal expenses

Ready to Explore Route 66 Part 1?

Reserve Your Spot

Questions? Call 360.260.9393 · Mon–Fri, 7–10am Pacific

Enhance Your Trip

Make your adventure even richer with these optional additions. Pre-nights and activities can be added at any time — before booking, during registration, or later via your trip advisor.

Single Supplement — Part 1 Pre-Night

Single room supplement for the May 4 pre-night in Chicago.

$144

Single Supplement — Part 1

Single room supplement for Part 1 (Chicago to Oklahoma City).

$689

Pre-Night in Chicago

Arrive a day early in Chicago before Route 66 Part 1 begins.

$154/night

Single Supplement — Part 2 Pre-Night

For the Route 66 Part 2

Single room supplement for the May 11 pre-night in Oklahoma City.

$84

Single Supplement — Part 2

For the Route 66 Part 2

Single room supplement for Part 2 (Oklahoma City to Santa Monica).

$990

Pre-Night in Oklahoma City

For the Route 66 Part 2

Arrive a day early in Oklahoma City before Part 2 begins.

$88/night

Oklahoma City National Memorial & Museum

For the Route 66 Part 2

Visit the deeply moving Oklahoma City National Memorial and Museum on the morning of Day 1. Self-guided admission included.

$15/personHalf day

Coleman Theater Evening

An evening at the historic Coleman Theatre Beautiful in Miami, Oklahoma.

$59/person

National Cowboy & Western Heritage Museum

For the Route 66 Part 2

Explore one of America's premier Western art and history museums in Oklahoma City, with exhibits spanning cowboy culture, rodeo, and frontier life.

$15/personHalf day

Available to add during registration or by calling 360.260.9393.

Before You Book

Start by browsing our tour calendar and finding the adventure that fits your interests, dates, and walking level. There are two ways to secure your spot. You can pre-register for $200 per person to express interest before full details are released — pre-registered travelers receive a Priority Booking Invitation with one week to register before remaining space opens to the general public. Full registration requires a non-refundable $500 deposit ($200 pre-registration + $300 additional, or $500 if registering directly). Final payment is due 90 days before departure and can be made online or mailed by check for a 1% discount. Final payment is non-refundable and non-transferable. You'll receive reminders before each deadline. About 2-3 weeks before departure, you'll receive a final email packet with hotel names, contact information, a list of fellow travelers, and a detailed daily schedule. All registrations are subject to our General Terms & Conditions. Questions? Call us at 360.260.9393 or email hello@walkingadventures.fun.

Yes to all three. Route 66 is designed as two independent tours that also work beautifully together. Part 1 runs Chicago to Oklahoma City. Part 2 runs Oklahoma City to Santa Monica. Each part is a complete experience on its own. Travelers booking both parts enjoy a seamless handoff in Oklahoma City — no need to fly home and back. Many travelers book one part first, then add the other once they see the itinerary.

Airfare is generally not included in the tour price. The starting point for each tour is the arrival airport or first hotel. We recommend booking your own flights so you can use your preferred airline, frequent flyer miles, or travel credit. When air travel is necessary within an itinerary (such as inter-island flights in the Azores), it is usually included in the tour price. We recommend contacting Laura Pfahler, the travel agent we work with, to help book your flight arrangements. Detailed arrival and departure airport information is provided on each tour page and in your registration materials.

Route 66 was officially established on November 11, 1926. This centennial year brings once-in-a-lifetime celebrations along the entire route — from small-town festivals and vintage car rallies to museum exhibitions and community events honoring the Mother Road's legacy. Walking Route 66 during its 100th year means experiencing the road at a moment when communities along the route are especially alive with pride and celebration. This won't happen again.

Once paid, your registration deposit is non-refundable. Final payment is due before departure — your tour page has the specific dates — and is non-refundable after the due date. We'll send you a reminder a week or two before each deadline so nothing sneaks up on you. If a tour doesn't reach the minimum number of participants needed to run, WAI may cancel the departure — and if that happens, you'll receive a full refund of everything you've paid. It's rare, but we want you to know where you stand. See our General Tour Conditions for complete cancellation and refund details.

WAI believes strongly in the importance of travel insurance for financial and medical protection from unforeseen circumstances before departure or during your adventure. We recommend a policy covering trip cancellation, medical evacuation, and emergency medical expenses. Be aware that some policies contain time-sensitive provisions — benefits like coverage of pre-existing conditions may only be available if the policy is purchased within a certain number of days of booking. Airfare is generally not covered by tour travel insurance. Using SquareMouth.com is a good way to compare pricing. Other options include Allianz, Travel Guard, and Travel Insured International. WAI bears no responsibility for travel insurance benefits advertised by credit card companies — verify coverage types and limits before relying on them.

Every WAI walk uses a two-part rating: a number (1–3) for incline and a letter (A–C) for terrain. Here’s what they look like:

1 — Gentle (gain < 200 ft)

2 — Moderate (gain 200–1,000 ft)

3 — Steep (gain 1,000–2,000 ft)

🏙️ PavedA — Paved (almost entirely on pavement)

🥾 TrailsB — Trails (well-groomed trails, few obstacles)

⛰️ RuggedC — Rugged (rocky, rooted paths, or soft sand)

Quick Reference

	🏙️ Paved	🥾 Trails	⛰️ Rugged
Gentle	🏙️ Paved	🥾 Trails	⛰️ Rugged
Moderate	🏙️ Paved	🥾 Trails	⛰️ Rugged
Steep	🏙️ Paved	🥾 Trails	⛰️ Rugged

Each tour page also has a Tour Pace rating (1–5) and a Walk Challenge rating (1–5) that summarize the overall difficulty. Use these to compare tours at a glance — then check the day-by-day itinerary for the full picture.

You'll receive a detailed packing list and final email packet about 2-3 weeks before departure, including hotel names, contact information, a list of fellow travelers, and a more detailed daily schedule. Key items for every WAI tour: well broken-in walking shoes (not new ones), layers for variable weather, a lightweight waterproof rain jacket, a small daypack for daily walks, sunscreen, and a hat. For international tours, check your tour page for destination-specific recommendations. Comfortable, modest clothing works for most group dinners — WAI tours are relaxed, not formal.

Most days begin with a group breakfast, followed by a morning walk or cultural visit. Midday includes a lunch stop — sometimes included, sometimes on your own at a local restaurant. Afternoons blend walking with sightseeing, and evenings are usually free with periodic group dinners. You'll never feel rushed, and there's always time to rest, explore on your own, or sit in a café and watch the world go by. Your guides will share a detailed daily schedule before the trip so you'll know exactly what to expect.

You don't need to be an athlete. WAI tours range from gentle strolls through city streets to more adventurous walks on hills and trails — and most walking days offer a shorter or easier alternative so you can choose your level. If you enjoy walking regularly and can handle a couple of miles at a comfortable pace, you'll find tours that fit. More experienced walkers will find plenty to challenge them too. The best preparation is to walk regularly in the weeks before your trip, gradually building up distance. Every tour page shows walk-by-walk ratings so you can see exactly what's involved — and if you're unsure, give us a call. We love helping people find the right fit.

WAI groups are small by design — every group is kept intentionally small so you're never just a face in the crowd. Two WAI guides accompany every trip (plus local national guides on international tours), which means more personal attention, better access to local experiences, and the kind of camaraderie that turns fellow travelers into lasting friends. Check your tour page for specific group size details.

Absolutely — and you won't be alone for long. Many of our travelers come solo and quickly find themselves part of the group. We offer a roommate matching service at no extra charge, or you can book a single room for a supplement (amount varies by tour). Solo travelers consistently tell us that the community feel of a WAI trip is one of the best parts.

Meal inclusions vary by tour — check your specific tour page for details. Most tours include daily breakfast, several group dinners, and select lunches. On free-meal days, your guides will recommend local restaurants that match the group's tastes and budget. Group dinners are a highlight — they're often at locally owned restaurants where the food tells a story about the place you're visiting.

With help from local experts and walking guides, Classic Curated itineraries are crafted with extensive on-site planning by WAI tour planners. Our objective is to capture the essence of a destination by weaving together its culture, history, natural beauty, and culinary traditions into a walking-centric adventure. Think of it as a fully planned trip where each day is thoughtfully designed — not a self-guided hike, not a resort stay, but an immersive journey with a small group led by experienced WAI guides.

After you register, we'll send you an Adventure Advice email with everything you need to plan your trip — recommended flights, arrival airports, timing tips, and important steps to take before departure. One big thing: please don't buy your flights until you've seen this email. It'll save you headaches and help you find the best options. Closer to departure, you'll get a final packet with hotel details, a list of your fellow travelers, and a day-by-day schedule.

If a tour departure doesn't reach the minimum enrollment needed to run, WAI reserves the right to cancel it. If that happens, registered participants receive a 100% refund of all payments made to WAI. Most tours reach minimum enrollment well in advance, and cancellations are rare — but we want you to know we stand behind our commitment if it ever happens. In cases where supplier non-refundable deposits limit what WAI can recover, we'll do our best to apply unrecovered amounts as credit toward a future tour.

Our approach to wellness on tour encourages travelers to: focus on health before the tour so you start healthy; pace yourself while on tour, as travel is inherently stimulating and can mask energy drain; stay hydrated and rested, especially on long-haul travel days and at altitude; and speak up if you're not feeling well — our guides are trained to help and would rather know early. We travel in small groups where everyone looks out for each other, and our guides carry first aid supplies and know local medical resources at every stop. Read our full Wellness on Tour Policy for details.

For Route 66 Part 2

The optional Grand Canyon South Rim excursion on the free day in Williams is spectacular — but it's also physically demanding. The rim sits at 7,000 feet elevation, and the walks (5 or 10 km) involve uneven terrain and exposure to sun and wind. If you've never seen the Grand Canyon, this is a remarkable opportunity. If you prefer a rest day, Williams itself is a charming Route 66 town with plenty to explore at a gentler pace.

For Route 66 Part 2

The walks on Route 66 are among the most accessible in our catalog — almost entirely flat (rated 1A) on paved surfaces, sidewalks, and well-maintained paths. The exceptions are Pecos Pueblo (2B, some uneven ground), Petrified Forest (2B, desert terrain), and the optional Grand Canyon (3B, elevation and rocky paths). This is a great tour for walkers who want cultural richness without extreme physical demands.

Route 66 Part 1

Tour Pace

Walk Challenge

Route 66 Part 1

Day-by-Day Itinerary

What's Included

Included

Not Included

Ready to Explore Route 66 Part 1?

Enhance Your Trip

Before You Book

You Might Also Love

Ready to Explore Route 66 Part 1?