The Midwest section of Route 66 is the birthplace of the famous highway, which was also known as the 'Will Rogers Highway' in honor of the humorist Will Rogers. Stretching through Illinois, Missouri, and Kansas, this section is the starting point of the entire Route 66 experience and provides a nostalgic look at the U.S. during the early 20th century, when Route 66 helped shape the country’s economy and culture.

Route 66 was established as a federal highway and quickly became the main highway for cross-country travel, facilitating migration, commerce, and tourism. It was recognized as the first highway of its kind, pioneering long-distance road travel in the United States. Whether you’re a history lover, nature lover, or simply someone wanting to explore the heart of America, the Midwest portion of Route 66 has something for everyone.

What Makes the Midwest Section of Route 66 Special?

The Midwest portion of Route 66 is not only the beginning of the famous highway but also offers a remarkable array of attractions that are deeply rooted in the history of America’s road-tripping culture. The Midwest offers a unique experience, combining the charm of small towns with the cultural influence of larger cities.

From Chicago, where Route 66 begins, to Kansas, with its brief yet iconic stretch, the Midwest is packed with historical landmarks, fun attractions, and a distinctive feel of Americana that’s hard to find anywhere else in the country.

What makes this section so special?

• Historical Significance: The Midwest is where Route 66 originated, and it’s packed with historic sites related to early American road culture. During the Great Depression, Route 66 served as the primary route for those who migrated west, acting as a lifeline for families, truckers, and migrants seeking new opportunities.

• Cultural Heritage: The region is known for its American nostalgia. The iconic motels, diners, and gas stations that line Route 66 evoke a sense of simpler times, offering a direct link to mid-20th-century American culture.

• Variety of Landscapes: While the Midwest may not have the rugged mountains or desert landscapes of the West, it boasts scenic farmland, quaint small towns, and rolling hills, offering travelers a picturesque yet laid-back road trip experience.

Must-See Attractions Along Route 66 in the Midwest

1. Historic Route 66 Illinois: The Birthplace

Length of Route 66 in Illinois: 300 miles

Illinois marks the eastern end of Route 66, serving as the starting point of this iconic highway. The route covers approximately 300 miles within the state. Originally, much of Route 66 in Illinois was a dirt road or graded dirt in many places, reflecting the rugged conditions before it was completely paved by 1938.

Over the years, many improvements were made to the Illinois section of Route 66 to enhance safety, speed, and efficiency. Several historic sites along the Illinois stretch are listed on the National Register of Historic Places, preserving the legacy of the route.

Key attractions along the Illinois portion include the Illinois State Fairgrounds, which hosts the Route 66 Experience exhibit year-round, as well as other notable stops. In Chicago, the historic road signs mark the beginning of Route 66, highlighting its significance as the birthplace of the Mother Road.

Key Attractions:

• Chicago: The starting point of Route 66, Chicago sets the tone for your journey with its iconic skyline, bustling streets, and deep-dish pizza. Start your trip at the Route 66 Start Sign at Adler Planetarium and visit landmarks like Millennium Park, the Art Institute of Chicago, and Navy Pier.

• Pontiac: A town brimming with Route 66 memorabilia, Pontiac is home to the Route 66 Hall of Fame & Museum, which features vintage photographs, a gift shop, and serves as a visitor center for travelers. Don’t miss the Giant Route 66 Shield, painted on the side of a building, which is one of the most popular photo ops along the route, or the quirky living mural that chronicles the highway’s history. While in Pontiac, stop by a classic soda fountain for a nostalgic treat and enjoy supporting local businesses that keep the spirit of Route 66 alive.

• Springfield: The hometown of Abraham Lincoln, Springfield offers history buffs plenty to explore. Visit the Abraham Lincoln Presidential Library and Museum, the Old State Capitol, and the Lincoln Tomb to immerse yourself in U.S. history. Don’t miss a local eatery known for its famous chicken pot pie, a comforting favorite among travelers.

• Coffeen: Stop in Coffeen, a smaller town, for Route 66 markers and scenic spots. Be sure to check out the Gateway to the West signs that mark important historical landmarks, and take time to support local businesses that make these small towns unique.

2. Missouri: The Gateway to the West

Length of Route 66 in Missouri: 300 miles

Key Attractions:

• St. Louis: Famous for the Gateway Arch, this city marks the transition from the eastern U.S. to the wild west. Route 66 passes through the east side and downtown St. Louis, highlighting the city's historical significance. The Old Chain of Rocks Bridge (also known as the old chain or rocks bridge) is a historic crossing at the north edge of the city, spanning the Mississippi River with its unique 22-degree bend and distinctive architecture. The National Museum of Transportation is a key stop for history buffs, while the National Blues Museum is a must-see for music lovers. Route 66 State Park offers a taste of the natural beauty that Missouri has to offer, with the park's visitor center featuring memorabilia and information about the route. The park is also located near the scenic Meramec River, a popular destination for outdoor activities. Family-friendly fun awaits at Six Flags St. Louis, a major amusement park along the route. Historic road signs mark key points, and some towns bypassed by the highway have become ghost towns. The Missouri section of Route 66 was once known for its dangerous curves, which were later realigned for safety.

• Cuba: Known for its colorful Route 66 murals, Cuba is also home to the historic Wagon Wheel Motel, which has been serving travelers since 1935. The town embodies the charm of old Route 66, with nostalgic stops at local diners and shops. A preserved vintage gas station stands as a roadside attraction, and visitors can admire classic neon signs and vintage signs that evoke the mid-century spirit of the route.

• Springfield: A major city along the route, Springfield is home to the Route 66 Car Museum, which showcases vintage cars that have traveled the historic route. Springfield also boasts some great eateries and a lively local scene.

• Fanning: The small town of Fanning is home to the World’s Largest Rocking Chair, a quirky stop that’s perfect for a photo op and a fun break during your road trip. The area also features nostalgic neon signs and vintage signs as part of the classic roadside experience.

• Red Cedar Inn: Located in Pacific, Missouri, the Red Cedar Inn is a historic stop built in 1934 from local logs. It now serves as a museum and visitor center, offering information about Route 66 and the original Red Cedar Inn Restaurant.

3. Kansas: A Short but Iconic Stretch of Route 66

Length of Route 66 in Kansas: 13 miles

Key Attractions:

• Galena: This tiny town may only have a short stretch of Route 66 near the Kansas-Missouri state line, but it’s packed with character. Cars on the Route is a popular stop, especially for fans of the movie Cars, which was inspired by Route 66. Don’t miss the Tow Mater statue and grab some Route 66 memorabilia while you’re there. In Galena, you can also find preserved sections of the old road, offering a glimpse into the highway’s early days when parts were still graded dirt before being fully paved.

• Riverton: Riverton is home to one of the last remaining historic Route 66 gas stations. This station is a great spot to grab a photo and reflect on the history of the main highway that connected the country’s heartland to the West Coast. The area also features stretches of the old road, preserved for visitors interested in the nostalgia and heritage of Route 66.

• Baxter Springs: Just a short drive from Galena, Baxter Springs offers a taste of local life, with its classic small-town charm and Route 66 nostalgia. Visit the Old Riverton Store for a real look at the Route 66 legacy, and learn about the new route realignments that have shaped travel through the region. This area played a significant role during World War II, as Route 66 was used for moving military equipment and transporting military equipment across the country, highlighting its importance as a main highway for military logistics. During the 1950s and 1960s, the Kansas stretch of Route 66 was also a popular path for vacationers heading west, contributing to the development of roadside attractions and motels along the route.

Cultural Events and Festivals Along Route 66

Traveling the historic Route 66 isn’t just about the open road and vintage neon signs—it’s also about the vibrant cultural events and festivals that keep the spirit of the “Mother Road” alive. Throughout the year, communities along this legendary route come together to celebrate their shared heritage, transforming the highway into a living museum of Americana. Whether you’re a history buff, a classic car enthusiast, or simply love a good street festival, Route 66 offers countless opportunities to immerse yourself in its unique culture.

In Illinois, the journey begins with a bang. The Route 66 International Festival in Springfield draws visitors from across the country, featuring classic car parades, live music, and local food that capture the essence of the “Main Street of America.” Pontiac’s Route 66 Hall of Fame and Museum is not only a treasure trove of memorabilia but also hosts the annual Illinois Route 66 Hall of Fame Induction Ceremony, where legends of the road are honored and stories of the original route are shared. These events are perfect for connecting with fellow travelers and learning more about the people who shaped the highway’s legacy.

Missouri keeps the celebration going with events centered around its historic sites. In St. Louis, the iconic Gateway Arch stands as a symbol of westward adventure, and the National Park Service often hosts special programs and guided tours that delve into the city’s role as a crossroads of American history. Festivals in the area frequently feature vintage cars, local music, and food trucks serving up Route 66 classics, all set against the backdrop of the city’s rich architectural heritage.

As you continue west, the festivities don’t stop. Oklahoma’s Route 66 Museum in Clinton offers interactive exhibits and hosts community events that bring the history of the United States highway system to life. In Texas, Amarillo’s Route 66 Festival is a lively celebration with classic car shows, live bands, and a bustling main street atmosphere. New Mexico’s Albuquerque Summerfest and Arizona’s Route 66 Days in Flagstaff both offer a blend of live entertainment, local cuisine, and family-friendly activities, all celebrating the enduring legacy of the route.

Even at the western end of the journey, the spirit of Route 66 shines bright. Santa Monica’s End of the Trail Festival marks the conclusion of the historic route with music, food, and festivities right by the Pacific Ocean, reminding travelers of the road’s lasting impact on American culture.

No matter where you join the route, these festivals and events are a fantastic way to experience the camaraderie and nostalgia that define Route 66. They offer a chance to explore historic sites, meet passionate locals, and see the “Mother Road” in all its glory. So, as you plan your next road trip, consider timing your adventure to coincide with one of these unforgettable celebrations—there’s no better way to experience the heart and soul of Route 66.

Why the Midwest is a Crucial Part of the Mother Road Americana

Route 66 in the Midwest holds a special place in American history. It was the original path that connected the rural Midwest with the urban East Coast and the rugged West. During the Great Depression, it became a lifeline for thousands of people migrating westward in search of better opportunities. The Midwest section, stretching from Chicago to the rolling hills of Missouri and Kansas, is steeped in this history, offering travelers the chance to experience the foundation of American road travel. For those heading west along Route 66, this region marks the beginning of an iconic journey across the country.

The Midwest offers an authentic piece of Americana—the roadside motels, diners, gas stations, and signs that are icons of the American road trip. Many of these establishments still stand today, evoking memories of simpler times and providing travelers with a glimpse into the past. Preservation efforts have ensured that many historic places along the route remain accessible, allowing visitors to connect with the cultural heritage of Route 66. Route 66 was the birthplace of American road culture, and in the Midwest, you’ll experience this history in the most authentic way, with all the charm of vintage Americana.

As you explore, you'll find not only classic attractions but also new destinations that have been added to enhance the travel experience. The decline of Route 66 began as the interstate highway system was completed, ultimately replacing the old road with faster, more efficient routes and leading to its removal from the U.S. Highway System.

How to Remember and Record Your Route 66 Adventure

One of the best parts about taking a road trip on Route 66 is the opportunity to capture your adventure. Whether you’re snapping photos, filming videos, or sharing your journey on social media, documenting your trip helps preserve the memories and share them with others. Here’s how you can record your Route 66 adventure through the Midwest and make the most of your trip:

Capture the Journey Through Photos

• Iconic Landmarks: The Midwest section is packed with photo-worthy stops, including the Gateway Arch in St. Louis, the World’s Largest Rocking Chair in Fanning, and the Cars on the Route in Galena. Don’t miss the opportunity to snap a photo at these iconic spots for a unique record of your journey.

• Historical Buildings: The Wagon Wheel Motel in Cuba and the Route 66 Hall of Fame & Museum in Pontiac are both visually interesting and historic. Capture the charm of these old-school establishments and their vintage neon signs.

• Nature and Views: The Missouri countryside offers scenic beauty, particularly in Route 66 State Park. Take photos of the rolling hills and peaceful landscapes, and don’t forget the picturesque Rainbow Bridge in Kansas.

Record Videos and Share Your Experience

• Time-Lapse Video: Capture the rolling landscape and changing scenes as you drive through the Midwest. A time-lapse video of your Route 66 journey provides an exciting visual representation of your adventure.

• GoPro or Drone Footage: If you have access to a GoPro or drone, take shots of the landscape and attractions from different angles. A bird’s-eye view of landmarks like Cuba’s murals or the Gateway Arch adds a dynamic element to your memories.

Use Social Media to Share Your Story

• Instagram: Use popular hashtags like #Route66 and #Route66Adventures to share your photos and connect with fellow travelers. Post your best shots of iconic signs, quirky roadside attractions, and your RV experience to inspire others.

• TikTok and YouTube: Create short videos documenting your favorite stops or giving your followers a tour of the Route 66 museums and historical sites. Show off quirky roadside attractions and record your experience of staying in vintage motels along the route.

Create a Travel Journal

A travel journal is a fantastic way to record your Route 66 experiences. Along with writing about your favorite moments, you can add tickets, brochures, or postcards from the places you visit. A journal also provides a personal account of the people you meet, the foods you try, and the things that make Route 66 special to you.

Travel Tips for the Midwest Section of Route 66

1. Time to Spend: To fully explore the Midwest section of Route 66, plan to spend 2–3 days in Illinois and Missouri, and a few hours in Kansas. The distances between major attractions are relatively short, so you can cover a lot of ground in a short period.

2. Fuel and Supplies: While Route 66 is well-served in Illinois and Missouri, some of the more remote stretches through smaller towns in Missouri and Kansas may have limited services. Be sure to fill up your gas tank and stock up on supplies in larger cities like St. Louis or Springfield.

3. Best Time to Visit: The best time to travel Route 66 in the Midwest is during spring and fall when the weather is mild, and many roadside attractions are in full swing. Summer can be hot, especially in Missouri, so consider visiting in the cooler months if you're not a fan of the heat.

Frequently Asked Questions (FAQ)

How long is the Route 66 stretch in Illinois, Missouri, and Kansas?

The total length of Route 66 through these states is approximately 600 miles, with about 300 miles in Illinois, 300 miles in Missouri, and 13 miles in Kansas.

What are the most famous stops along Route 66 in the Midwest?

Key highlights include the Gateway Arch in St. Louis, the Route 66 Hall of Fame Museum in Pontiac, and the Cars on the Route in Galena. Other notable stops include the Wagon Wheel Motel in Cuba and the World’s Largest Rocking Chair in Fanning.

What are the major cities along Route 66?

Major cities along Route 66 include Chicago, St. Louis, Oklahoma City, Albuquerque, and Los Angeles. Oklahoma City is a key stop, offering travelers a vibrant downtown and a rich Route 66 history.

Where does Route 66 officially begin and end?

Route 66 officially begins in Chicago and ends in Santa Monica, California. The western terminus is at the intersection of Lincoln and Olympic boulevards in Santa Monica, near downtown Los Angeles, marking the iconic endpoint of the historic highway.

How much time should I spend in the Midwest section of Route 66?A: Depending on how much you want to explore, spending 2–3 days in the Midwest section is ideal. This allows you to enjoy both the urban sights and the quieter, scenic stretches of the route.

Can I travel the entire Midwest section of Route 66 in an RV?

Absolutely! The Midwest section of Route 66 is very RV-friendly, with many campgrounds and motels along the way. Just be prepared for some stretches through smaller towns where services might be sparse, and plan your fuel stops accordingly.

Is there anything to do in the Kansas section of Route 66?

Although the Kansas stretch is short, it’s packed with unique stops like the Rainbow Bridge in Riverton and Cars on the Route in Galena. It’s a quick but memorable leg of the journey.

Start Your Trip on Route 66

The Midwest section of Route 66 offers a unique blend of history, culture, and scenic beauty, making it one of the most important and exciting parts of this historic road trip. From the iconic Gateway Arch in St. Louis to the quirky Cars on the Route in Kansas, the Midwest portion of Route 66 gives travelers a deeper look at Americana and the nation’s history. Whether you’re an avid Route 66 enthusiast or someone new to the highway, this region offers something for everyone.

Book your RV today with Cruise America and set off on a journey through the heart of America, where every mile of Route 66 tells a story of the past and present.