Before you start mapping out your dream Route 66 road trip, it’s worth knowing which cities are absolute must-stops along the way. The Mother Road stretches over 2,400 miles from Chicago to Los Angeles, winding through small towns, quirky roadside attractions, and some of the most iconic cities in America. These urban hubs are where history meets modern adventure—where Route 66 legends were born and where road trippers can find everything from neon-lit diners to deep dives into local culture.
From the towering skyline of Chicago, where the journey begins, to the sun-soaked streets of Los Angeles at the end of the road, each major city along Route 66 offers its own unique flavor. You’ll find places rich with Route 66 nostalgia, like Springfield, Missouri, where the highway got its name, and Albuquerque, where neon signs still glow in the desert night. Some cities, like St. Louis and Tulsa, seamlessly blend historic landmarks with big-city attractions, while others, like Amarillo and Santa Fe, offer a taste of the wide-open West.
Whether you’re looking to step into the past at a classic motor court, chow down on local specialties, or explore Route 66 history, these 12 major cities should be on your itinerary. Buckle up, because we’re about to take a city-by-city tour of some of the best places to visit along America’s most legendary highway.
Major Cities on Route 66
Chicago, Illinois
Every great journey starts somewhere—why not at the very beginning?
Chicago, Illinois, is the official starting point of Route 66, making it a must-visit city for any road trip along the Mother Road. Situated on the shores of Lake Michigan, Chicago is the third-largest city in the United States, with a population of nearly 2.7 million people. It’s a bustling metropolis filled with world-class attractions, deep-dish pizza, and rich history.
For Route 66 travelers, Chicago is where it all begins. The historic starting point of the route was originally at Jackson Boulevard and Michigan Avenue, later moved to Adams Street. This city marks the moment where travelers turn their wheels westward toward adventure. Whether you’re snapping a photo at the “Begin Route 66” sign or fueling up on iconic Chicago eats, it’s the perfect place to kick off your journey.
Expect towering skyscrapers, vibrant neighborhoods, and an electric energy that sets the tone for the miles ahead. Take time to explore world-renowned museums, stroll along the Riverwalk, and experience the legendary music and food scene before hitting the open road.
Must-See Stops: The Route 66 Sign and Mural at Navy Pier, Begin Route 66 Sign, Lou Mitchell’s, The Art Institute of Chicago, Millennium Park, Cloud Gate (“The Bean”), Willis Tower Skydeck, Navy Pier
Where to Stay: The Blackstone, W Chicago, Congress Plaza Hotel, Palmer House Hilton, The Gwen
Springfield, Illinois
History, highways, and a hearty helping of nostalgia—Springfield is a Route 66 must-stop!
Springfield, the capital of Illinois, sits about 200 miles south of Chicago and is home to around 113,000 residents. While it’s well-known as the city where Abraham Lincoln lived before becoming president, it’s also a significant stop along Route 66, offering travelers a mix of history, classic roadside charm, and local flavors.
For Route 66 road trippers, Springfield is a key stop filled with iconic attractions. The city was a major hub when the highway was first established, and remnants of that golden age still remain. From classic diners to quirky roadside stops, Springfield keeps the Route 66 spirit alive.
Expect to find a blend of presidential history and Mother Road nostalgia. Visit Lincoln’s historic sites, snap a photo at a giant fiberglass muffler man, and don’t leave without trying a famous Springfield specialty—the Horseshoe Sandwich, a local favorite loaded with fries and cheese sauce.
Must-See Stops: Cozy Dog Drive-In, Route 66 Motorheads Bar & Museum, The Lauterbach Giant, Shea’s Gas Station Museum, Abraham Lincoln Presidential Library & Museum, The Illinois State Capitol
Where to Stay: State House Inn, Inn at 835, The Route 66 Hotel
St. Louis, Missouri
Get your kicks—and a stunning skyline view—at the Gateway to the West!
Straddling the Mississippi River, St. Louis is Missouri’s second-largest city, home to over 300,000 residents and a rich mix of history, culture, and Route 66 nostalgia. As one of the first major stops west of the Illinois border, St. Louis has long been a crossroads for travelers, making it a significant city along the Mother Road.
For Route 66 road trippers, St. Louis marks an exciting transition into Missouri, offering a mix of vintage highway charm and big-city attractions. While the original Route 66 alignments through the city have shifted over time, travelers can still follow the path of the old road and discover iconic landmarks along the way.
Expect to find a blend of historic Route 66 stops, delicious St. Louis-style barbecue, and breathtaking views from the Gateway Arch. Take a drive down Chippewa Street to see classic neon signs, stop for a frozen treat at a beloved custard stand, and soak in the city’s rich history before continuing west.
Must-See Stops: Gateway Arch National Park, Ted Drewes Frozen Custard, Chain of Rocks Bridge, The Museum of Transportation
Where to Stay: St. Louis Union Station, Drury Plaza Hotel St. Louis at The Arch, Magnolia St. Louis
Springfield, Missouri
Welcome to the birthplace of Route 66—where the Mother Road got its name!
Springfield, Missouri, is more than just another stop along Route 66—it’s where the highway officially got its name. On April 30, 1926, at a meeting held in Springfield, officials decided on the now-famous “Route 66” designation, forever linking the city to the history of the highway. With a population of around 170,000, Springfield is the third-largest city in Missouri and a major stop for road trippers exploring the Ozarks.
For Route 66 travelers, Springfield offers a mix of classic roadside attractions, vintage diners, and a deep connection to the highway’s legacy. The city has preserved its Mother Road heritage, with retro motels, historic landmarks, and a welcoming atmosphere that makes it a great place to rest and explore.
Expect a blend of history, nostalgia, and local flavor. Visit museums dedicated to Route 66, snap a photo with a giant fork, and grab a meal at a classic diner that has served road-weary travelers for decades. Springfield is a place where the past and present of Route 66 come together.
Must-See Stops: Route 66 Springfield Visitor Center, Birthplace of Route 66 Roadside Park, Gillioz Theatre, World’s Second Largest Fork, Birthplace of Route 66 Monument, Birthplace Plaza, History Museum on the Square
Where to Stay: Best Western Route 66 Rail Haven, Rockwood Motor Court, Hotel Vandivort
Tulsa, Oklahoma
Neon lights, Art Deco sights, and a whole lot of Route 66 history—welcome to Tulsa!
Tulsa, Oklahoma, is one of the most vibrant cities along Route 66, blending historic charm with modern attractions. With a population of about 400,000, it’s the second-largest city in Oklahoma and a key stop along the Mother Road. Tulsa played a major role in the early days of Route 66, with the highway cutting right through town and leaving behind a legacy of classic diners, vintage motels, and stunning Art Deco architecture.
For Route 66 travelers, Tulsa is a must-stop destination filled with history and iconic landmarks. The city has embraced its Route 66 roots, preserving historic buildings and adding new attractions that celebrate the highway’s past. Whether you’re exploring its thriving arts scene, hunting for neon signs, or grabbing a bite at a classic drive-in, Tulsa delivers a perfect mix of nostalgia and city life. Plus, for lovers of roadside quirk, Tulsa is quickly becoming a Land of the Giants, with five Route 66 muffler men and Uniroyal Gals in the Route 66 district.
Expect to find a city rich in history, from its early oil boom days to its deep connection to Route 66. Take a drive down 11th Street, Tulsa’s main Route 66 stretch, and you’ll find restored gas stations, quirky roadside attractions, and some of the best food along the highway.
Must-See Stops: Meadow Gold Sign, Cyrus Avery Centennial Plaza, Buck Atom’s Cosmic Curios, The Blue Dome District, Route 66 Historical Village, The Golden Driller
Where to Stay: The Campbell Hotel, Hotel Indigo, Ambassador Hotel, Desert Hills Motel
Oklahoma City, Oklahoma
Big city energy meets classic Route 66 charm in the heart of Oklahoma!
Oklahoma City, the capital of Oklahoma, is the largest city along Route 66 in the state, with a population of nearly 700,000. Situated right in the middle of the Mother Road’s path, OKC has long been a major stop for travelers making their way west. The city blends modern attractions with historic Route 66 landmarks, making it a must-visit destination for road trippers.
For Route 66 travelers, Oklahoma City offers a mix of vintage roadside stops, cultural attractions, and a deep connection to the highway’s history. It’s a place where past and present collide in the best way possible.
Expect to find a dynamic city with a little bit of everything—historic Route 66 landmarks, a thriving arts and entertainment district, and plenty of spots to fuel up on classic Oklahoma eats. Whether you’re stopping to see a giant milk bottle or diving into the city’s cowboy culture, OKC is packed with reasons to pull over and stay awhile.
Must-See Stops: Milk Bottle Grocery, Tower Theatre, Gold Dome Building, National Cowboy & Western Heritage Museum
Where to Stay: Classen Inn, The Skirvin Hotel, Colcord Hotel
Amarillo, Texas
Everything’s bigger in Texas—including the Route 66 attractions!
Amarillo is the largest city on Route 66 in the Texas Panhandle, with a population of about 200,000. Located right in the middle of the vast Texas plains, it has long been a crucial stop for travelers making their way along the Mother Road. Amarillo embraces its Route 66 history with classic diners, quirky roadside attractions, and wide-open stretches of highway.
For Route 66 travelers, Amarillo is a city packed with roadside fun. Whether you’re spray-painting a car at the world-famous Cadillac Ranch, grabbing a meal at an old-school steakhouse, or exploring a stretch of the city’s preserved Route 66 Historic District, there’s no shortage of things to see and do.
Expect to find a true taste of Texas with a Route 66 twist. Amarillo is home to neon-lit motels, massive steaks (seriously, a 72-ounce one), and some of the most iconic roadside attractions on the entire highway. Get ready for a city that’s as bold and unforgettable as the road that runs through it.
Must-See Stops: Cadillac Ranch, The Big Texan Steak Ranch, Route 66 Historic District, Amarillo Route 66 Visitors Center, Jack Sisemore Traveland RV Museum, Slug Bug Ranch
Where to Stay: The Barfield, The Big Texan Motel, Atrea Inn, Route 66 Inn
Santa Fe, New Mexico
Where Route 66 took the scenic route—and so should you!
Santa Fe, the capital of New Mexico, is one of the most unique cities along Route 66. With a population of about 90,000, it’s known for its rich history, Pueblo-style adobe architecture, and thriving arts scene. Though later alignments of Route 66 bypassed Santa Fe in favor of a more direct route through Albuquerque, the original 1926 alignment wound through this beautiful high-desert city, making it an essential stop for history-minded road trippers.
For Route 66 travelers, Santa Fe offers a mix of historic charm, cultural attractions, and stunning scenery. The city’s deep Native American, Spanish, and Old West influences create an atmosphere unlike anywhere else on the Mother Road. Whether you’re exploring the historic Plaza, visiting centuries-old churches, or browsing the many galleries along Canyon Road, Santa Fe is a place that invites you to slow down and take it all in.
Expect to find a city filled with art, history, and incredible Southwestern cuisine. Santa Fe’s original Route 66 alignment may have been rerouted, but the spirit of the road still lingers in its historic streets and well-preserved landmarks.
Must-See Stops: Santa Fe Plaza, San Miguel Chapel, The Miraculous Staircase at Loretto Chapel, The Palace of the Governors, Canyon Road, Meow Wolf
Where to Stay: El Rey Court, La Fonda on the Plaza, The Mystic Santa Fe, Inn of the Governors
Albuquerque, New Mexico
Neon lights, vintage motels, and the longest urban stretch of Route 66—welcome to Albuquerque!
Albuquerque is the largest city in New Mexico and one of the most important stops along Route 66. With a population of over 560,000, it sits right in the heart of the state and boasts the longest urban stretch of the Mother Road. Route 66 runs straight through town on Central Avenue, where neon signs, retro motels, and classic diners keep the highway’s spirit alive.
For Route 66 travelers, Albuquerque offers a mix of old and new. You’ll find well-preserved motor lodges, historic theaters, and plenty of roadside oddities. The city also has a rich cultural heritage, with deep Native American and Spanish influences that are reflected in its architecture, art, and cuisine. Whether you’re cruising past vintage neon signs or exploring Old Town’s adobe-lined streets, Albuquerque is a city that blends the past and present beautifully.
Expect to find a Route 66 destination full of color, character, and classic roadside charm. And if you time your trip right, you might even catch the world-famous Albuquerque International Balloon Fiesta, where hundreds of hot air balloons fill the sky.
Must-See Stops: Route 66 Crossing Sign, 66 Diner, Dog House Drive, KiMo Theatre, Old Town Albuquerque, National Museum of Nuclear Science & History
Where to Stay: El Vado Motel, The Monterey Motel, Bottger Mansion of Old Town, Casas de Suenos Old Town Historic Inn
Flagstaff, Arizona
High-altitude adventure and Route 66 nostalgia—welcome to Flagstaff!
Nestled in the mountains at an elevation of nearly 7,000 feet, Flagstaff is a Route 66 city that offers a cool, pine-scented contrast to the desert landscapes of Arizona. With a population of about 75,000, it’s known for its outdoor recreation, historic downtown, and deep ties to both Route 66 and the railroad. The Mother Road runs right through town, and vintage motels, neon signs, and classic diners still line the route, keeping the spirit of the highway alive.
For Route 66 travelers, Flagstaff is a perfect mix of history and adventure. It’s home to the famous Lowell Observatory, where Pluto was discovered, and serves as a gateway to natural wonders like the Grand Canyon, just 80 miles to the north. The city’s historic downtown, with its brick buildings and bustling restaurants, is a great place to stretch your legs and soak in some classic Route 66 charm.
Expect to find a vibrant city where Route 66 meets the great outdoors. Whether you’re stopping for a night or using Flagstaff as a base for nearby attractions, this is a must-visit spot on any Mother Road itinerary.
Must-See Stops: NAU Skydome Lumberjack Muffler Man, Historic Route 66 Downtown District, Lowell Observatory, Museum of Northern Arizona, Walnut Canyon National Monument, Museum Club (Currently Closed), Miz Zip’s
Where to Stay: Hotel Monte Vista, Americana Motor Hotel, Western Hills Motel, High Country Motor Lodge, Little America Hotel, Weatherford Hotel
San Bernardino, California
The final stretch of Route 66 starts here—where history meets the highway!
San Bernardino, a major city in Southern California, is one of the last big stops on Route 66 before reaching the end of the road in Santa Monica. With a population of about 220,000, it has long been a key gateway for travelers making their way west. As one of the first California cities Route 66 travelers encountered, San Bernardino became a hub of motels, diners, and service stations catering to those chasing the American dream along the Mother Road.
For Route 66 travelers, San Bernardino is packed with history. It’s home to one of the most famous roadside icons—the very first McDonald’s, which opened in 1948. The city also played a big role in car culture, with historic cruise nights and drive-ins that once defined the Route 66 experience.
Expect to find a city that embraces its Route 66 heritage with museums, classic eateries, and plenty of vintage signs that still dot the landscape. San Bernardino might be close to the end of the road, but it’s a stop that proves the journey is just as important as the destination.
Must-See Stops: The Original McDonald’s Museum, Wigwam Motel, California Theatre of the Performing Arts, San Manuel Stadium
Where to Stay: Wigwam Motel, Sunshine Motel, Hilton Garden Inn
Los Angeles & Santa Monica, California
The end of the road, but not the end of the adventure!
Santa Monica, California, in Los Angeles County, is where Route 66 meets the Pacific Ocean, marking the official end of the Mother Road. As the second-largest city in the United States, LA sprawls across more than 500 square miles, home to nearly 4 million people. But for road trippers, it’s more than just a big city—it’s the grand finale of an unforgettable journey.
Route 66 has been guiding travelers west to Los Angeles since the highway’s inception in 1926. For Dust Bowl migrants, it was a path to opportunity. For mid-century vacationers, it was the gateway to Hollywood glamour and sun-soaked beaches. Today, reaching the end of Route 66 at Santa Monica Pier is a rite of passage for road trippers, a moment to soak in the salty breeze and reflect on the miles behind.
In LA and Santa Monica, expect a mix of history, pop culture, and classic roadside nostalgia. Snap a photo at the famous “End of the Trail” sign, stroll the Hollywood Walk of Fame, or grab a burger at an old-school drive-in. Whether you’re into vintage neon, scenic ocean views, or iconic movie locations, this is the ultimate road trip reward.
Must-See Stops: Santa Monica Pier, Route 66 “End of the Trail” sign, 66-to-Cali, Chicken Boy, Hollywood Walk of Fame, Griffith Observatory, Universal Studios Hollywood
Where to Stay: The Georgian Hotel, The Beacon, Fairmont Miramar Hotel & Bungalows, Palm Motel
Route 66 offers a journey through time, a cross-country adventure that connects some of America’s most vibrant cities. From the towering skyline of Chicago to the sun-soaked shores of Los Angeles, each major stop along the way tells a story of history, culture, and the ever-evolving spirit of the open road.
These 12 cities showcase the diverse landscapes and experiences that make Route 66 such an iconic drive. Whether you’re marveling at the Gateway Arch in St. Louis, exploring the vibrant art scene in Albuquerque, or standing at the edge of the Pacific in Los Angeles, every city adds its own unique chapter to your Route 66 story. No matter how you experience it, Route 66 is a journey that stays with you long after the last mile.
So, which cities will you add to your Route 66 road trip? The adventure is yours to create—just grab a map, hit the road, and get ready to make memories on the Mother Road!
