Celebrating a Centennial: The Ultimate Route 66 Adventure from Chicago to Grapevine

Route 66 is more than just a highway; it is a journey through the heart of America, capturing the essence of its diverse landscapes, cultures, and histories. From the architectural marvels of Chicago to the sun-kissed beaches of Santa Monica, Route 66 offers an unforgettable exploration of the American spirit. Whether traveling east to west or vice versa, the Mother Road promises an adventure filled with discovery, nostalgia, and the open road’s endless possibilities.

Here are two great itineraries for exploring Route 66:

The Eastern Expedition: Chicago to Grapevine

The eastern portion of Route 66 begins in the dynamic city of Chicago, Illinois, known for its stunning architecture and cultural landmarks. Travelers can explore Millennium Park, take an architectural tour, or delve into the city’s rich history through its museums and public art. The route from Chicago offers a mix of urban excitement and historical charm as it winds through Illinois, with notable stops in towns like Joliet and Pontiac, showcasing Route 66’s heritage through murals, classic diners, and museums.

Heading south, travelers reach St. Louis, Missouri, home to the iconic Gateway Arch. St. Louis offers a blend of historical and modern attractions, including the Missouri Botanical Garden, the historic Soulard district, and the vibrant Delmar Loop. The city’s rich culture and historical significance make it a key stop on Route 66.

Missouri’s segment of Route 66 is filled with small-town charm and natural beauty, with Springfield standing out for its historic sites and the picturesque Ozarks. Key attractions include the Route 66 Car Museum and Fantastic Caverns.

As the journey continues through Oklahoma, travelers experience Southern hospitality and Western charm. Tulsa and Oklahoma City highlight the state’s cultural diversity and rich heritage. Tulsa is known for its art deco architecture and vibrant arts scene, while Oklahoma City offers cowboy culture and urban attractions such as the National Cowboy & Western Heritage Museum and Stockyards City.

The eastern expedition concludes in Grapevine, Texas. This charming city, located in the Dallas-Fort Worth metroplex, is renowned for its historic downtown, wineries, and the Grapevine Vintage Railroad. Grapevine’s blend of history, culture, and modern amenities makes it a perfect end to the eastern journey.

For more detailed information on this segment, visit the Route 66 East itinerary.

The Western Expedition: Grapevine to Santa Monica

The western segment of Route 66 picks up in Grapevine, Texas, offering a gateway to the diverse landscapes and cultural tapestries of the American Southwest. The journey begins with stops in Durant and Duncan, Oklahoma, where travelers can immerse themselves in Native American heritage at the Choctaw Cultural Center and explore the history of the Chisholm Trail at the Chisholm Trail Heritage Center.

Rejoining Route 66 in Oklahoma City, travelers can explore a variety of attractions, including the First Americans Museum, the National Cowboy & Western Heritage Museum, and the lively Bricktown district. Oklahoma City’s blend of historical and modern experiences enriches the Route 66 journey.

Heading westward into Texas, travelers encounter Amarillo, a city known for its quirky charm epitomized by the Cadillac Ranch and a vibrant art scene. The journey continues into New Mexico, where Santa Fe and Albuquerque offer a mix of cultural and natural attractions. Santa Fe’s Pueblo-style architecture and artistic community provide a serene experience, while Albuquerque’s old town and Balloon Fiesta add whimsy and wonder.

Arizona’s stunning landscapes greet travelers next, with key stops in Holbrook, Flagstaff, and Kingman. These destinations offer opportunities to explore natural wonders such as the Painted Desert, Petrified Forest, and the Grand Canyon. The small-town charm and historical significance of these Arizona towns enhance the Route 66 adventure.

The journey reaches its western terminus in Santa Monica, California. The iconic Santa Monica Pier marks the end of Route 66, offering stunning ocean views and a vibrant beach culture. Santa Monica’s attractions include the Pacific Park amusement park, the Third Street Promenade, and the Original Muscle Beach. The city’s coastal charm and vibrant urban scene make it a fitting end to the Route 66 journey.

For more detailed information on this segment, visit the Route 66 West itinerary.

Learn more about Grapevine Convention & Visitors Bureau