The Ultimate 15-Day Guide to Exploring Route 66 🇺🇸

Spanning nearly 2,500 miles from Chicago to Los Angeles, Route 66 is the quintessential American road trip, packed with history, charm, and endless adventure. Known as the “Main Street of America,” this legendary route passes through eight states and offers a deep dive into Americana, from vintage diners to quirky roadside attractions and natural wonders. Here’s a detailed, day-by-day itinerary to help you make the most out of your journey.

Day 1: Arrival in Chicago

Start your journey in the bustling city of Chicago, the official beginning of Route 66. Spend the day exploring Chicago’s iconic landmarks, like Millennium Park, the Willis Tower, and Navy Pier. Don’t miss out on deep-dish pizza or a Chicago-style hot dog! Rest up for an early departure tomorrow as you set off on your Route 66 adventure.

Day 2: Chicago to Springfield, Illinois (via Pontiac)

On your first official Route 66 leg, you’ll drive through the charming town of Pontiac, where you can visit the Route 66 Hall of Fame and Museum. Continue to Springfield, the birthplace of Abraham Lincoln, and immerse yourself in history at the Abraham Lincoln Presidential Library and Museum.

• Must-See: Route 66 Hall of Fame and Museum, Lincoln Home National Historic Site
• Stay: Springfield (2 nights)

Day 3: Springfield to St. Louis, Missouri

As you approach St. Louis, stop by the Chain of Rocks Bridge, an iconic Route 66 landmark. Once in the city, explore the famous Gateway Arch, the tallest arch in the world, and visit historic neighborhoods like The Hill, known for its Italian heritage.

• Must-See: Gateway Arch, Missouri Botanical Garden, St. Louis Zoo
• Stay: St. Louis

Day 4: St. Louis to Branson, Missouri (via Meramec Caverns)

Today, head southwest towards Branson, stopping at the Meramec Caverns, a famous hideout for the notorious outlaw Jesse James. Enjoy a scenic drive through the Ozarks before reaching Branson, a city known for its lively entertainment scene and beautiful lakes.

• Must-See: Meramec Caverns, Branson’s 76 Strip
• Stay: Branson

Day 5: Branson to Oklahoma City, Oklahoma (via Claremore)

On this leg, pass through Claremore, where you can visit the Will Rogers Memorial Museum dedicated to the beloved humorist. Continue to Oklahoma City, a city rich in cowboy culture and Native American history.

• Must-See: Will Rogers Memorial Museum
• Stay: Oklahoma City (2 nights)

Day 6: Oklahoma City Sightseeing

Spend your day exploring Oklahoma City’s attractions, like the National Cowboy & Western Heritage Museum and the Bricktown entertainment district. Take a moment at the Oklahoma City National Memorial to honor those affected by the 1995 bombing.

• Must-See: National Cowboy Museum, Bricktown, Oklahoma City National Memorial

Day 7: Oklahoma City to Amarillo, Texas (via Route 66 Museum)

En route to Amarillo, visit the Oklahoma Route 66 Museum in Clinton, which offers fascinating exhibits about the history of the highway. Upon reaching Amarillo, check out the Cadillac Ranch, an art installation featuring cars buried nose-first in the ground.

• Must-See: Oklahoma Route 66 Museum, Cadillac Ranch
• Stay: Amarillo

Day 8: Amarillo to Albuquerque, New Mexico

Today, drive across the Texas panhandle into New Mexico, reaching the vibrant city of Albuquerque. Known for its adobe buildings and breathtaking sunsets, Albuquerque is a great place to soak in Southwestern culture.

• Must-See: Old Town Albuquerque, Sandia Peak Tramway
• Stay: Albuquerque (2 nights)

Day 9: Albuquerque Sightseeing

Take a leisurely day to explore Albuquerque. Visit Old Town, a historic district filled with shops, galleries, and restaurants. Ride the Sandia Peak Tramway for panoramic views of the city and beyond.

Day 10: Albuquerque to Flagstaff, Arizona

Continuing west, drive through red-rock country to Flagstaff, Arizona. Along the way, enjoy the desert scenery and make a pit stop in Gallup, known for its Native American art and crafts.

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• Must-See: Downtown Flagstaff, Historic Route 66 Motels
• Stay: Flagstaff

Day 11: Flagstaff to Grand Canyon National Park (via Cameron Trading Post)

Today, head north to the Grand Canyon, stopping at the historic Cameron Trading Post for Navajo crafts and local art. Spend your afternoon marveling at the grandeur of the Grand Canyon, one of the natural wonders of the world.

• Must-See: Cameron Trading Post, South Rim of the Grand Canyon
• Stay: Grand Canyon National Park

Day 12: Grand Canyon to Las Vegas, Nevada (via Seligman)

Leaving the Grand Canyon, drive through Seligman, a town famous for its Route 66 memorabilia and colorful murals. Continue to the vibrant city of Las Vegas, where you can relax, explore, and enjoy world-class entertainment.

• Must-See: Seligman, Las Vegas Strip
• Stay: Las Vegas (2 nights)

Day 13: Las Vegas Sightseeing

Spend your day experiencing Las Vegas! Whether you’re interested in the dazzling casinos, incredible shows, or simply enjoying a buffet, Vegas has something for everyone.

• Must-See: The Strip, Bellagio Fountains, Fremont Street Experience

Day 14: Las Vegas to Los Angeles, California

Begin your final leg towards Los Angeles, passing through the Mojave Desert. As you enter California, take in the final miles of Route 66, stopping by iconic attractions like the Santa Monica Pier, where the route officially ends.

• Must-See: Santa Monica Pier, Hollywood Walk of Fame
• Stay: Los Angeles

Day 15: Departure from Los Angeles

Wrap up your journey with a relaxing day in Los Angeles. Enjoy the beaches, iconic landmarks, and vibrant neighborhoods like Venice Beach and Beverly Hills before you head home.

10 Things You May Not Know About Route 66 🚗🇺🇸

1. Not the Longest Highway: While Route 66 is famous, it’s not the longest U.S. highway. That title belongs to U.S. Route 20, which runs from Boston to Oregon.
2. Birth of the American Diner: The growth of Route 66 led to the establishment of classic American diners, bringing affordable, fast meals to travelers.
3. A Lifeline in the Dust Bowl: During the Great Depression, Route 66 served as an escape route for thousands fleeing the Dust Bowl region.
4. Military Support: During WWII, Route 66 was vital for moving military equipment and personnel across the country.
5. Historic Significance: Route 66 became the first fully paved transcontinental highway in America by 1938, revolutionizing road travel.
6. A Pop Culture Icon: Songs, movies, and TV shows have immortalized Route 66, like the popular song “(Get Your Kicks on) Route 66” by Bobby Troup.
7. Vintage Roadside Attractions: From neon signs to quirky motels, Route 66 is known for its unique roadside attractions, drawing tourists from around the world.
8. Mother Road’s Decline and Revival: With the construction of the Interstate Highway System, Route 66 lost much of its traffic but has seen a resurgence as a historic and scenic route.
9. Route 66 Festivals: Many towns along the route host annual festivals celebrating its history, bringing together car enthusiasts, musicians, and food vendors.
10. Endless Stories and Legends: Every town on Route 66 has its own unique stories, from infamous outlaws to stories of hope and resilience during the Great Depression.

Route 66 is more than a road; it’s a journey through America’s heart and soul. From bustling cities to sleepy towns, majestic natural wonders to quirky roadside attractions, the Mother Road offers an unforgettable travel experience. Whether you’re a history buff, adventure seeker, or simply a curious traveler, Route 66 promises memories that will last a lifetime.