10 Best Road Trip Stops Along America's Iconic Route 66

Lisette Marie
May 26, 2025

Route 66, often referred to as the "Main Street of America," is more than just a highway; it is an emblem of freedom and exploration, capturing the imagination of travelers for nearly a century. Spanning approximately 2,448 miles from Chicago, Illinois, to Santa Monica, California, this iconic road is a symbol of the American spirit. It traverses eight states, each offering a unique tapestry of landscapes, cultures, and histories. The road invites adventurers to embark on a journey through small towns, bustling cities, and picturesque countryside, capturing the essence of America's heartland. As we explore these 10 must-see stops, we'll uncover the hidden gems and iconic landmarks that make Route 66 a journey worth taking. So buckle up and prepare for a journey through America's heartland, where every mile brings a new story and every stop is a chapter in the great American road trip.

1. Chicago, Illinois - The Starting Point

Chicago, Illinois, USA Cityscape. Photo Credit: Envato @SeanPavone

The journey along Route 66 begins in Chicago, Illinois, a city known for its architectural marvels, vibrant culture, and rich history. As the starting point of this legendary road, Chicago offers travelers a dynamic blend of urban excitement and historical significance. Before hitting the road, take time to explore the city's iconic landmarks, such as the Willis Tower, Millennium Park, and the Art Institute of Chicago. Each of these sites provides a glimpse into the city's diverse cultural landscape and its role as a major hub of American industry and innovation. Chicago's connection to Route 66 is deeply rooted in its history as a transportation and commerce center. The city served as a gateway for travelers heading west, and its bustling streets were the launching point for countless journeys along the Mother Road. Visitors can explore the Route 66 Begin sign on Adams Street, a symbolic marker that signifies the start of the adventure. The city's vibrant neighborhoods, such as Wicker Park and Logan Square, offer a taste of local life, with eclectic dining options, unique shops, and lively entertainment venues.

As travelers prepare to embark on their Route 66 odyssey, Chicago sets the tone for the journey ahead. The city's rich history, diverse culture, and dynamic energy provide a fitting backdrop for the start of an adventure that promises to be both thrilling and transformative. Whether you're exploring the city's iconic landmarks or delving into its vibrant neighborhoods, Chicago offers a captivating introduction to the journey along Route 66.

2. Springfield, Illinois - A Step Back in Time

Historic Route 66 in Springfield, Illinois. Cozy dog drive-in. Photo Credit: Wikimedia Commons @Gorup de Besanez

As travelers leave the bustling streets of Chicago behind, they journey into the heart of Illinois, where Springfield awaits with its rich historical tapestry. Springfield, the capital of Illinois, is a city steeped in history, most notably as the home of Abraham Lincoln before he became the 16th President of the United States. A visit to Springfield is like stepping back in time, offering a glimpse into the life and legacy of one of America's most revered leaders. The Abraham Lincoln Presidential Library and Museum is a must-see attraction that provides an immersive experience into Lincoln's life and times. Through interactive exhibits and historical artifacts, visitors can explore Lincoln's journey from humble beginnings to the presidency. Additionally, the Lincoln Home National Historic Site offers a chance to tour the only home Lincoln ever owned, providing insight into his family life and personal history.

Springfield's connection to Route 66 is also celebrated through various attractions and events. The Cozy Dog Drive-In, a Route 66 original, serves the famous "cozy dog," a corn dog on a stick that has become a staple for road trippers. The Route 66 Drive-In Theater offers a nostalgic experience, allowing travelers to enjoy classic films under the stars. As a city that blends history with nostalgia, Springfield offers a unique stop along Route 66, inviting travelers to explore the past while enjoying the classic Americana that defines the journey.

3. St. Louis, Missouri - Gateway to the West

St. Louis, Missouri, USA city skyline and park. Photo Credit: Envato @SeanPavone

Continuing westward, the journey along Route 66 leads to St. Louis, Missouri, a city known as the "Gateway to the West." St. Louis is a vibrant metropolis that offers a mix of cultural attractions, historical landmarks, and modern amenities. The city's most iconic symbol is the Gateway Arch, a 630-foot monument that stands as a testament to the spirit of exploration and westward expansion. Visitors can take a tram ride to the top of the arch for breathtaking views of the city and the Mississippi River. St. Louis has a rich history as a major port city and a hub of commerce and culture. The Missouri History Museum offers exhibits that delve into the city's past, from its role in the fur trade to its significance during the westward expansion. The city is also home to the Anheuser-Busch Brewery, where visitors can tour the historic brewery and sample some of the world's most famous beers.

Route 66 travelers will find plenty to explore in St. Louis, from the vibrant neighborhoods of The Loop and Soulard to the lush landscapes of Forest Park. The city's culinary scene is a highlight, offering everything from classic barbecue to innovative cuisine. As a gateway city, St. Louis serves as a bridge between the Midwest and the West, providing a dynamic stop along Route 66 that captures the essence of American exploration and adventure.

4. Meramec Caverns, Missouri - A Natural Wonder

Meramec Caverns, Jesse James Hideout, Stanton, Missouri. Photo Credit: Wikimedia Commons @Ronincmc

A short drive from St. Louis, travelers will discover one of Missouri's most captivating natural attractions: the Meramec Caverns. Located in Stanton, these caverns are a geological wonder, offering a mesmerizing underground landscape of stalactites, stalagmites, and other stunning formations. The caverns have been a popular tourist destination since the 1930s, drawing visitors with their beauty and mystery. The Meramec Caverns offer guided tours that take visitors deep into the heart of the caves, where they can marvel at the natural formations and learn about the caverns' history and geology. The "Wine Room," with its delicate calcite formations, and the "Stage Curtain," a massive sheet of rock, are just two of the highlights that showcase the caverns' natural artistry. The caverns also have a storied past, rumored to have been a hideout for the infamous outlaw Jesse James.

In addition to exploring the caverns, visitors can enjoy a range of outdoor activities in the surrounding area, including hiking, canoeing, and zip-lining. The Meramec River provides a scenic backdrop for these adventures, offering a chance to experience the natural beauty of Missouri's landscape. As a stop along Route 66, the Meramec Caverns provide a unique opportunity to connect with nature and explore the hidden wonders beneath the surface.

5. Tulsa, Oklahoma - The Oil Capital of the World

A Frisco line Meteor steam locomotive displayed at the Route 66 Historical Village, a nostalgic park along historic U.S. Route 66 as it winds through Tulsa, Oklahoma. Called “The Mother Road” by its aficionados, Route 66 was the original paved, mostly tw. Photo Credit: Wikimedia Commons @Mr Mines Engine

As travelers continue their journey along Route 66, they enter Oklahoma, where the city of Tulsa awaits with its rich history and vibrant culture. Known as the "Oil Capital of the World," Tulsa played a significant role in the American oil industry and has since evolved into a thriving city with a diverse array of attractions. The city's skyline is a testament to its prosperous past, with art deco architecture that reflects the wealth and optimism of the early 20th century. Tulsa's connection to Route 66 is celebrated through various landmarks and attractions. The Cyrus Avery Centennial Plaza honors the "Father of Route 66" and features a bronze sculpture depicting the Avery family on the Mother Road. The Tulsa Route 66 Historical Village offers a glimpse into the city's transportation history, with restored train cars and a replica of a 1920s gas station. Visitors can also explore the Blue Dome District, a vibrant area known for its nightlife, dining, and entertainment.

In addition to its Route 66 heritage, Tulsa offers a rich cultural scene with world-class museums, galleries, and performing arts venues. The Philbrook Museum of Art, housed in a stunning Italian Renaissance villa, features an impressive collection of art from around the world. The city's music scene is also noteworthy, with a strong tradition of jazz and blues that continues to thrive today. As a stop along Route 66, Tulsa offers a dynamic blend of history, culture, and modern-day excitement.

6. Oklahoma City, Oklahoma - A City of Resilience

The Oklahoma City National Memorial stands as a poignant tribute to those affected by the tragic bombing on April 19, 1995. It encompasses the sacred ground where the Alfred P. Murrah Federal Building once stood, now transformed into a place of quiet refl. Photo Credit: Wikimedia Commons @xiquinhosilva

Continuing westward, travelers arrive in Oklahoma City, a city known for its resilience and vibrant spirit. As the capital of Oklahoma, the city offers a mix of historical attractions, cultural experiences, and modern amenities. Oklahoma City's history is deeply intertwined with Route 66, and the city embraces its heritage with pride, offering visitors a chance to explore its unique connection to the Mother Road. The Oklahoma City National Memorial and Museum is a poignant tribute to the victims of the 1995 bombing of the Alfred P. Murrah Federal Building. The memorial and museum provide a space for reflection and remembrance, offering insight into the city's resilience and strength in the face of tragedy. The Bricktown District, a revitalized warehouse area, offers a lively atmosphere with restaurants, shops, and entertainment venues, providing a vibrant contrast to the city's somber history.

Oklahoma City's connection to Route 66 is celebrated through various attractions, including the Route 66 Park, which features walking trails, a skate park, and a playground, all designed to honor the historic highway. The city also hosts events and festivals that celebrate its Route 66 heritage, drawing visitors from near and far. As a stop along Route 66, Oklahoma City offers a unique blend of history, culture, and community spirit, inviting travelers to explore its past while experiencing its vibrant present.

7. Amarillo, Texas - The Heart of the Panhandle

Caution Wet Paint" is written inside a heart on one of the Cadillacs, offering a unique perspective of the liminal nature of the graffiti at the Cadillac Ranch. Photo Credit: Wikimedia Commons @TinyCatMistress

As travelers cross into Texas, they arrive in Amarillo, a city known as the "Heart of the Panhandle." Amarillo offers a taste of the Wild West, with its wide-open spaces, cowboy culture, and rugged landscapes. The city's connection to Route 66 is celebrated through various attractions and landmarks, making it a must-see stop along the journey. One of Amarillo's most iconic attractions is the Cadillac Ranch, an art installation featuring ten vintage Cadillacs buried nose-first in the ground. Visitors are encouraged to bring spray paint and add their own artistic touch to the cars, creating a constantly evolving canvas of color and creativity. The Big Texan Steak Ranch is another Route 66 staple, famous for its 72-ounce steak challenge, where diners attempt to consume the massive meal in under an hour.

Amarillo's connection to the cowboy culture is evident in its annual events, such as the Tri-State Fair and Rodeo, which celebrate the region's agricultural heritage and Western traditions. The American Quarter Horse Hall of Fame & Museum offers insight into the history and significance of the American Quarter Horse, a breed closely associated with the cowboy lifestyle. As a stop along Route 66, Amarillo provides a unique opportunity to experience the spirit of the West and the hospitality of Texas.

8. Santa Fe, New Mexico - A Tapestry of Cultures

Enjoying my walk at the beautiful Santa Fe Plaza. Photo Credit: Wikimedia Commons @WikTalksmart

As travelers venture further west, they arrive in Santa Fe, New Mexico, a city known for its rich cultural tapestry and stunning natural beauty. Santa Fe is the oldest capital city in the United States, offering a unique blend of Native American, Spanish, and Anglo cultures. The city's adobe architecture, vibrant arts scene, and stunning landscapes make it a captivating stop along Route 66. Santa Fe's historic Plaza is the heart of the city, offering a bustling hub of activity with shops, galleries, and restaurants. The Palace of the Governors, located on the Plaza, is a National Historic Landmark that provides insight into the region's history and cultural heritage. The Georgia O'Keeffe Museum celebrates the life and work of the renowned artist, whose paintings of the New Mexico landscape have become iconic.

Santa Fe's connection to Route 66 is celebrated through various attractions and events, including the annual Santa Fe Indian Market, which showcases the work of Native American artists from across the country. The city's vibrant arts scene is complemented by its stunning natural surroundings, with opportunities for hiking, skiing, and exploring the nearby Sangre de Cristo Mountains. As a stop along Route 66, Santa Fe offers a rich tapestry of cultures and experiences, inviting travelers to explore its unique blend of history and creativity.

9. Flagstaff, Arizona - Gateway to the Grand Canyon

Lowell Observatory main entrance in Flagstaff, Az. Photo Credit: Wikimedia Commons @Marine 69-71

As travelers approach the western edge of Route 66, they arrive in Flagstaff, Arizona, a city known as the "Gateway to the Grand Canyon." Flagstaff offers a unique blend of natural beauty, outdoor adventure, and cultural attractions, making it a perfect stop along the journey. The city's location at the base of the San Francisco Peaks provides a stunning backdrop for exploration and adventure. Flagstaff's connection to Route 66 is celebrated through various attractions, including the Historic Downtown District, which offers a charming mix of shops, restaurants, and historic buildings. The Museum of Northern Arizona provides insight into the region's natural and cultural history, with exhibits on Native American cultures, geology, and archaeology. The Lowell Observatory, where Pluto was discovered, offers stargazing opportunities and educational programs for visitors of all ages.

Flagstaff's proximity to the Grand Canyon makes it an ideal base for exploring one of the world's most iconic natural wonders. The Grand Canyon National Park offers breathtaking views, hiking trails, and opportunities for wildlife viewing, providing a once-in-a-lifetime experience for travelers. As a stop along Route 66, Flagstaff offers a gateway to adventure and discovery, inviting travelers to explore the natural beauty and cultural richness of the region.

10. Kingman, Arizona - The Heart of Route 66

Historic Route 66 in Kingman, Az. Photo Credit: Wikimedia Commons @Marine 69-71

Continuing westward, travelers arrive in Kingman, Arizona, a city known as the "Heart of Route 66." Kingman offers a rich history and a strong connection to the Mother Road, making it a must-see stop along the journey. The city's location in the Mojave Desert provides a stunning backdrop for exploration and adventure. Kingman's connection to Route 66 is celebrated through various attractions, including the Route 66 Museum, which offers exhibits on the history and significance of the highway. The museum provides insight into the people and places that have shaped the road's legacy, offering a glimpse into the past and present of this iconic route. The city's Historic Downtown District offers a charming mix of shops, restaurants, and historic buildings, providing a taste of classic Americana.

Kingman's location in the Mojave Desert offers opportunities for outdoor adventure, with hiking trails, scenic drives, and opportunities for wildlife viewing. The nearby Hualapai Mountains provide a stunning backdrop for exploration, offering a chance to experience the natural beauty of the region. As a stop along Route 66, Kingman offers a unique blend of history, culture, and adventure, inviting travelers to explore the heart of the Mother Road.

10. Santa Monica, California - The Journey's End

Route 66 Santa Monica End of the trail. Photo Credit: Envato @rawf8

The journey along Route 66 concludes in Santa Monica, California, where the road meets the Pacific Ocean. Santa Monica offers a vibrant blend of beachside beauty, cultural attractions, and modern amenities, making it a fitting end to the adventure. The city's iconic Santa Monica Pier serves as a symbolic endpoint for travelers, offering a mix of entertainment, dining, and stunning ocean views. Santa Monica's connection to Route 66 is celebrated through various attractions and landmarks. The Route 66 End of the Trail sign on the pier marks the conclusion of the journey, providing a photo opportunity and a chance to reflect on the adventure. The city's vibrant arts scene, with galleries, theaters, and cultural events, offers a dynamic contrast to the natural beauty of the beach.

Santa Monica's location on the Pacific Ocean provides opportunities for outdoor adventure, with surfing, biking, and beachcombing among the popular activities. The city's culinary scene offers a diverse array of dining options, from fresh seafood to international cuisine, providing a taste of California's diverse flavors. As the journey along Route 66 comes to an end, Santa Monica offers a vibrant and fitting conclusion, inviting travelers to relax and reflect on the adventure of a lifetime.

Author Image
Lisette Marie
A creative problem-solver with expertise across digital marketing, writing, and web development. Dedicated to building effective solutions and telling powerful stories that lead to meaningful impact.

Latest

Latest