The Ultimate Route 66 Road Trip Itinerary

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Route 66, known as the “Main Street of America,” is more than just a highway—it’s a journey through the heart of the United States, filled with history, nostalgia, and iconic roadside attractions. Spanning nearly 2,500 miles from Chicago to Santa Monica, this legendary route takes you through a diverse landscape of small towns, vibrant cities, and breathtaking scenery. Whether you’re a history buff, a lover of quirky attractions, or just looking for an epic adventure, Route 66 has something for everyone. Here’s your ultimate guide to making the most of every stop along the way.

1. Chicago, Illinois: The Start of the Journey

Must-See Attraction: The Route 66 Sign

• The journey begins at the historic “Begin Route 66” sign at the intersection of Adams Street and Michigan Avenue. This iconic spot is perfect for a commemorative photo to kick off your adventure.

Highlights:

• The Art Institute of Chicago: This world-class museum is home to an impressive collection of art from around the globe. Be sure to see Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte, two of the most famous pieces on display. The museum itself is an architectural masterpiece, featuring a mix of classical and modern design.
• Millennium Park: A hub of activity in downtown Chicago, Millennium Park is where you’ll find the iconic “Cloud Gate,” affectionately known as “The Bean.” This stainless-steel sculpture reflects the city’s skyline and is a popular spot for photos. The park also hosts free concerts and art installations.
• Willis Tower Skydeck: Standing 1,450 feet tall, Willis Tower (formerly Sears Tower) was once the tallest building in the world. The Skydeck offers breathtaking views of the city and Lake Michigan. For the brave, step out onto “The Ledge,” a glass box extending 4.3 feet outside the building for an unobstructed view below.

Insider Tip: Before hitting the road, indulge in a Chicago-style deep-dish pizza at Lou Malnati’s or Giordano’s. These iconic pizzerias offer the city’s signature dish, a must-try before you embark on your journey. Consider taking a pizza tour to learn more about Chicago’s history and to try some of the best pizzas in the city.

2. Springfield, Illinois: Lincoln’s Legacy

Must-See Attraction: Abraham Lincoln Presidential Library and Museum

• This museum offers a comprehensive look at the life and legacy of one of America’s greatest presidents. The exhibits are interactive and engaging, featuring artifacts from Lincoln’s life, such as his stovepipe hat, and vivid recreations of key moments in history.

Highlights:

• Cozy Dog Drive-In: Claiming to be the birthplace of the corn dog, Cozy Dog Drive-In is a Route 66 landmark. The “Cozy Dog” is a delicious treat, perfect for a quick bite on the road. The diner also offers a nostalgic atmosphere with Route 66 memorabilia lining the walls.
• Lincoln Home National Historic Site: Tour the preserved home of Abraham Lincoln, where he lived with his family before becoming president. The home is beautifully maintained, offering a glimpse into the domestic life of the 16th president.
• Route 66 Drive-In Theatre: Experience a classic American pastime at this retro drive-in. It’s one of the few remaining drive-ins on Route 66, showing double features on weekends. Bring some popcorn and enjoy a movie under the stars.

Insider Tip: While in Springfield, visit the Illinois State Capitol, an architectural marvel with a stunning dome and intricate interior design. Guided tours are available, providing insight into the state’s legislative process.

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

Must-See Attraction: The Gateway Arch

• The Gateway Arch is not only a symbol of St. Louis but also a tribute to the westward expansion of the United States. Standing at 630 feet, it’s the tallest man-made monument in the country. Take a tram ride to the top for panoramic views of the city and the Mississippi River.

Highlights:

• Ted Drewes Frozen Custard: A St. Louis institution since 1929, Ted Drewes is famous for its “concretes,” frozen custard so thick that it’s served upside down. The stand is a favorite stop for locals and Route 66 travelers alike, offering a variety of flavors and toppings.
• Old Chain of Rocks Bridge: This historic bridge, once a part of Route 66, spans the Mississippi River. It’s now a pedestrian and bike path, offering stunning views of the river and the city. The bridge is known for its unique 22-degree bend in the middle.
• City Museum: Housed in a former shoe factory, the City Museum is an eclectic mix of playground, funhouse, and architectural marvel. It’s filled with tunnels, slides, and secret passages, all made from repurposed industrial materials. It’s a must-visit for families and anyone with a sense of adventure.

Insider Tip: Take some time to explore the Missouri Botanical Garden, one of the oldest botanical gardens in the U.S. The garden features beautiful landscapes, historic structures, and a stunning Japanese Garden.

4. Cuba, Missouri: Mural City

Must-See Attraction: Historic Murals

• Known as “Mural City,” Cuba features a collection of large, colorful murals that depict the town’s history and its connection to Route 66. These murals are spread throughout the town, making for a fun walking tour that’s both educational and visually striking.

Highlights:

• The Wagon Wheel Motel: One of the oldest continuously operating motels on Route 66, The Wagon Wheel Motel is a charming place to stay. The motel has been meticulously restored, offering vintage-style accommodations with modern amenities. Its neon sign is a classic Route 66 photo opportunity.
• Crawford County History Museum: This museum offers a deep dive into the local history of Crawford County and its significance on Route 66. The exhibits include everything from Native American artifacts to vintage automobiles.
• Fanning 66 Outpost: Home to the world’s largest rocking chair, this roadside attraction is a fun stop for photos and souvenirs. The outpost also offers Route 66 memorabilia and local crafts.

Insider Tip: For a true taste of Missouri, stop by Missouri Hick Bar-B-Q. This restaurant is known for its mouthwatering smoked meats, including ribs, brisket, and pulled pork, served with a variety of tangy sauces.

5. Carthage, Missouri: Small-Town Charm

Must-See Attraction: The 66 Drive-In Theatre

• The 66 Drive-In Theatre is a nostalgic stop on Route 66, offering a classic drive-in movie experience. The theatre dates back to 1949 and has been lovingly maintained, making it a perfect place to enjoy a double feature under the stars.

Highlights:

• The Precious Moments Chapel: Even if you’re not a collector, the Precious Moments Chapel is a unique and serene stop. The chapel is decorated with murals and stained glass inspired by the famous Precious Moments figurines, created by artist Samuel Butcher. The grounds are peaceful and beautifully landscaped.
• Boots Court Motel: A quintessential Route 66 motel, Boots Court has hosted travelers since the 1930s, including Hollywood star Clark Gable. The motel has been restored to its 1940s glory, with period-appropriate furnishings and décor. It’s a perfect place to experience vintage Route 66 hospitality.
• Carthage Civil War Museum: Learn about the Battle of Carthage, the first major land battle of the Civil War, at this small but informative museum. The museum offers exhibits on local history and artifacts from the Civil War era.

Insider Tip: Don’t miss the Jasper County Courthouse, a stunning example of Romanesque Revival architecture. The courthouse is the centerpiece of the town square, surrounded by shops and cafes, and it’s particularly beautiful when lit up at night.

6. Oklahoma City, Oklahoma: Western Heritage

Must-See Attraction: The National Cowboy & Western Heritage Museum

• This museum is a treasure trove of Western art, culture, and history. The exhibits include everything from Native American artifacts to cowboy gear and Western movie memorabilia. The museum’s expansive collection of Western art is particularly impressive, featuring works by Frederic Remington and Charles M. Russell.

Highlights:

• Pops 66 Soda Ranch: Located in Arcadia, just outside Oklahoma City, Pops 66 Soda Ranch is famous for its 66-foot-tall soda bottle sculpture that lights up in neon at night. Inside, you’ll find over 700 varieties of soda from around the world, along with a retro diner serving classic American fare.
• Route 66 Park: Situated on the west side of Oklahoma City, this park is a tribute to the Mother Road. It features a walking trail lined with interpretive signs detailing the history of Route 66, as well as a replica of the original roadbed. There’s also a playground and a scenic lake, making it a great stop for families.
• Bricktown Entertainment District: Once a warehouse district, Bricktown has been revitalized into Oklahoma City’s premier entertainment area. It’s home to a variety of restaurants, bars, shops, and a scenic canal where you can take a water taxi ride. It’s a lively spot to spend an evening.

Insider Tip: While in Oklahoma City, visit the Oklahoma City National Memorial & Museum, a poignant and moving tribute to the victims of the 1995 bombing. The outdoor memorial is open 24 hours a day, with a reflecting pool, symbolic Gates of Time, and the Survivor Tree.

7. Amarillo, Texas: The Lone Star State’s Quirky Side

Must-See Attraction: Cadillac Ranch

• Cadillac Ranch is one of Route 66’s most iconic and quirky attractions. This public art installation features ten Cadillacs buried nose-down in a field, with their tail fins sticking up. The cars are covered in layers of spray paint, and visitors are encouraged to add their own graffiti. It’s a colorful and ever-changing piece of art.

Highlights:

• The Big Texan Steak Ranch: Known for its 72-ounce steak challenge (finish it in under an hour, and it’s free), The Big Texan is a must-visit for any meat lover. Even if you’re not up for the challenge, the restaurant offers a wide variety of steaks, ribs, and other Texas-sized dishes. The decor is Western-themed, with plenty of kitsch and character.
• Route 66 Historic District: Amarillo’s Historic District along Route 66 is lined with antique shops, art galleries, and restaurants. It’s a great place to take a leisurely stroll, explore unique shops, and soak in the retro atmosphere.
• Amarillo Zoo: A fun stop for families, the Amarillo Zoo is home to over 80 species of animals, including big cats, primates, reptiles, and exotic birds. The zoo is set in Thompson Park, which also offers picnic areas, playgrounds, and a lake.

Insider Tip: For a unique experience, visit Palo Duro Canyon State Park, just south of Amarillo. Often referred to as the “Grand Canyon of Texas,” it offers stunning landscapes, hiking trails, and the outdoor musical drama “TEXAS,” performed in the summer months.

8. Albuquerque, New Mexico: A Blend of Cultures

Must-See Attraction: Old Town Albuquerque

• Old Town Albuquerque is the heart of the city’s history, with its adobe buildings, Spanish colonial architecture, and vibrant cultural scene. Explore the historic San Felipe de Neri Church, browse the local shops, and enjoy traditional New Mexican cuisine at one of the many restaurants.

Highlights:

• The Albuquerque International Balloon Fiesta: If your road trip coincides with early October, you’re in for a treat. The Albuquerque International Balloon Fiesta is the world’s largest hot air balloon festival, featuring hundreds of colorful balloons filling the sky at dawn and dusk. Feeling adventurous? Consider taking your own hot air balloon ride. This Albuquerque Hot Air Balloon ride at Sunrise operates year-round, ready to give you amazing views of Albuquerque and the surrounding areas.
• The Sandia Peak Tramway: Take a ride on the Sandia Peak Tramway, one of the longest aerial tramways in the world. The tram takes you 2.7 miles up to the 10,378-foot peak of the Sandia Mountains, offering breathtaking views of the Rio Grande Valley and beyond.
• The Indian Pueblo Cultural Center: Learn about the history, culture, and art of New Mexico’s 19 Pueblo tribes at this fascinating museum. The center also hosts traditional dance performances and has a great gift shop featuring Native American crafts.

Insider Tip: Visit the Petroglyph National Monument, where you can see ancient rock carvings left by Native American and Spanish settlers. The monument offers several hiking trails that lead you past hundreds of these fascinating petroglyphs.

9. Flagstaff, Arizona: Gateway to the Grand Canyon

Must-See Attraction: Lowell Observatory

• Flagstaff is home to Lowell Observatory, where Pluto was discovered in 1930. The observatory offers public tours, stargazing sessions, and exhibits on astronomy and space exploration. It’s a must-visit for anyone interested in the night sky.

Highlights:

• Walnut Canyon National Monument: Explore ancient cliff dwellings built by the Sinagua people over 700 years ago. The site features a scenic trail that takes you down into the canyon and through the well-preserved ruins.
• Meteor Crater: Just outside Flagstaff, Meteor Crater is one of the best-preserved meteorite impact sites on Earth. The visitor center offers exhibits on meteor science, and you can walk along the rim of the massive crater.
• The Museum of Northern Arizona: This museum offers a deep dive into the natural and cultural history of the Colorado Plateau. The exhibits cover everything from Native American art and artifacts to geology and paleontology.

Insider Tip: Flagstaff is a great base for visiting the Grand Canyon, located about 80 miles to the north. Consider making a side trip to one of the world’s most iconic natural wonders.

10. Kingman, Arizona: Heart of Route 66

Must-See Attraction: The Historic Route 66 Museum

• Located in the Powerhouse Visitor Center, the Historic Route 66 Museum in Kingman offers a detailed history of the Mother Road. The exhibits include vintage cars, road signs, and memorabilia, all telling the story of the people and places along Route 66.

Highlights:

• The Mojave Museum of History and Arts: This museum offers exhibits on the history of northwestern Arizona, including Native American artifacts, mining equipment, and old photographs. It’s a great place to learn about the region’s rich history.
• Cool Springs Station: Just outside Kingman, Cool Springs Station is a restored 1920s gas station and gift shop. The station is located along the scenic and winding Oatman Highway, part of the original Route 66.
• Route 66 Drive-Thru Shield: This quirky attraction in Kingman is a giant Route 66 shield that you can drive through. It’s a fun photo op and a unique piece of Route 66 history.

Insider Tip: Take a detour to the town of Oatman, a former gold mining town turned tourist attraction. Oatman is famous for its wild burros that roam the streets, as well as its gunfight reenactments and quirky shops.

11. Santa Monica, California: The End of the Road

Must-See Attraction: The End of the Trail Sign

• Your journey comes to an end at the Santa Monica Pier, where you’ll find the iconic “End of the Trail” sign marking the conclusion of Route 66. The pier itself is a bustling attraction with restaurants, shops, and an amusement park.

Highlights:

• Santa Monica Pier: The pier is home to Pacific Park, an amusement park with a Ferris wheel offering stunning views of the Pacific Ocean. The pier also has an aquarium, arcade games, and plenty of dining options.
• Third Street Promenade: A vibrant pedestrian shopping district in downtown Santa Monica, the Third Street Promenade is lined with shops, cafes, and street performers. It’s a great place to unwind and do some shopping after your long journey.
• Palisades Park: This scenic park runs along the bluffs overlooking the Pacific Ocean, offering beautiful walking paths, gardens, and spectacular views of the coastline. It’s a peaceful spot to reflect on your journey before heading home.

Insider Tip: If you have time, explore nearby Venice Beach, known for its eclectic boardwalk, Muscle Beach, and the Venice Canals. It’s a lively area that captures the laid-back vibe of Southern California.

Weird Things to See on Route 66:

One of the most charming aspects of Route 66 is the abundance of quirky, offbeat attractions that pepper the landscape. These oddities add character to your road trip and make for memorable stops along the way. Here are some of the weirdest and most wonderful attractions you won’t want to miss:

1. The Blue Whale of Catoosa – Catoosa, Oklahoma

• What It Is: A giant blue whale sculpture that sits in a pond, this roadside attraction was originally built in the 1970s as an anniversary gift from a husband to his wife. It quickly became a popular stop for Route 66 travelers, and today, it’s one of the most recognizable landmarks on the road.

2. The Leaning Tower of Texas – Groom, Texas

• What It Is: A water tower that appears to be leaning at a precarious angle, this structure was intentionally tilted by its builder as a roadside curiosity.

3. The World’s Largest Rocking Chair – Fanning, Missouri

• What It Is: Standing at an impressive 42 feet tall, this gigantic rocking chair was once the largest in the world. While it’s no longer the official record holder, it remains a popular stop on Route 66.

4. The Gemini Giant – Wilmington, Illinois

• What It Is: A towering fiberglass statue of a spaceman holding a rocket, the Gemini Giant is one of the last remaining “Muffler Men,” a series of giant advertising figures from the 1960s.

5. The Wigwam Motel – Holbrook, Arizona

• What It Is: A vintage motel where the rooms are shaped like large concrete teepees, the Wigwam Motel is a piece of Americana that harks back to the golden age of car travel.

6. The Bottle Tree Ranch – Oro Grande, California

• What It Is: A forest of “trees” made from metal pipes adorned with colorful glass bottles, Bottle Tree Ranch is the creation of artist Elmer Long. The bottles catch the sunlight, creating a kaleidoscope of colors.

7. The Totem Pole Park – Foyil, Oklahoma

• What It Is: A collection of hand-carved totem poles, including the world’s largest at 90 feet tall, Totem Pole Park is a tribute to Native American culture by artist Ed Galloway.

8. The Devil’s Rope Museum – McLean, Texas

• What It Is: A museum dedicated entirely to barbed wire, also known as “devil’s rope.” The museum explores the history, variations, and uses of this often-overlooked material.

Detours Just Off Route 66

While Route 66 is packed with iconic attractions, some of the most memorable experiences lie just a short detour away. Whether you’re seeking natural wonders, historic sites, or quirky roadside stops, these off-the-beaten-path gems are well worth the drive.

1. Meramec Caverns, Missouri

Located about 30 minutes off Route 66 near Stanton, Missouri, Meramec Caverns is a massive limestone cave system that has been a popular tourist attraction since the 1930s. The caverns are steeped in history, with legends of Jesse James using them as a hideout. Today, you can take a guided tour through the stunning formations, including the massive “Stage Curtain” and the underground “Wine Table.”

2. Cahokia Mounds, Illinois

Located just a 20-minute drive from St. Louis, Cahokia Mounds is a prehistoric Native American city that once thrived as the largest urban center north of Mexico. This UNESCO World Heritage site features over 80 mounds, including the massive Monks Mound, and offers a glimpse into the lives of the Mississippian people who built this complex society over a thousand years ago.

3. Lincoln’s Tomb, Illinois

A short drive from Springfield, Illinois, takes you to Oak Ridge Cemetery, where Abraham Lincoln, the 16th President of the United States, is laid to rest. The impressive monument and tomb are surrounded by statues and plaques commemorating Lincoln’s life and legacy. It’s a poignant stop for history buffs and anyone looking to pay their respects.

4. Red Rock Canyon State Park, Oklahoma

Just a short detour from Route 66 near Hinton, Oklahoma, Red Rock Canyon State Park offers stunning red rock cliffs, hiking trails, and picnic spots. The canyon was once a stop for settlers on the California Trail, and today, it’s a peaceful retreat where you can explore nature, camp, or simply enjoy the unique scenery.

5. Santa Fe, New Mexico

A 60-mile detour from Albuquerque, the historic city of Santa Fe offers a rich blend of Native American, Spanish, and Anglo cultures. Explore the vibrant art scene, stroll through the historic Plaza, visit the Georgia O’Keeffe Museum, or indulge in the city’s renowned Southwestern cuisine. Santa Fe’s adobe architecture and cultural heritage make it a unique and rewarding stop.

6. The Blue Hole, New Mexico

Located in Santa Rosa, New Mexico, about 15 minutes off Route 66, The Blue Hole is a natural artesian spring that’s become a popular spot for scuba diving and swimming. With crystal-clear water and a depth of 80 feet, this oasis in the desert offers a refreshing break from the road. It’s a surprising and serene stop that adds a splash of adventure to your journey.

7. Grand Canyon National Park, Arizona

A short drive from Williams, Arizona, the Grand Canyon is one of the most awe-inspiring natural wonders in the world. Just 60 miles north of Route 66, this UNESCO World Heritage site offers breathtaking vistas, hiking trails, and opportunities for adventure. Whether you take in the views from the South Rim, embark on a mule ride, or catch a sunset, the Grand Canyon is an unforgettable detour.

8. Petrified Forest National Park, Arizona

Situated about 20 miles off Route 66 near Holbrook, Petrified Forest National Park is home to one of the world’s largest and most colorful concentrations of petrified wood. The park also features the stunning Painted Desert, ancient petroglyphs, and remnants of prehistoric villages. It’s a fascinating stop for both geology enthusiasts and history buffs.

9. Oatman, Arizona

About 30 minutes off Route 66 near Kingman, the old mining town of Oatman is a quirky blast from the past. Nestled in the Black Mountains, Oatman is famous for its wild burros that roam the streets and its daily staged gunfights. The town’s rustic charm and Old West atmosphere make it a fun and entertaining detour.

10. Meteor Crater, Arizona

Just a 30-minute drive from Winslow, Arizona, Meteor Crater is one of the best-preserved meteorite impact sites in the world. This massive crater, measuring nearly a mile wide, was created around 50,000 years ago by a meteorite impact. The visitor center offers exhibits on the science behind meteor impacts, and you can even walk along the rim for spectacular views.

11. Walnut Canyon National Monument, Arizona

Located about 20 minutes off Route 66 near Flagstaff, Walnut Canyon National Monument is home to ancient cliff dwellings built by the Sinagua people over 800 years ago. The park’s trails allow you to explore these well-preserved ruins and enjoy the beautiful canyon views. It’s a fascinating glimpse into the lives of the region’s early inhabitants.

Route 66 Road Trip Tips

Plan Ahead: While spontaneity is part of the fun, having a rough itinerary helps ensure you don’t miss any must-see attractions. Research each stop, and consider booking accommodations in advance, especially in smaller towns where options may be limited.

Stay Flexible: Road trips are about the journey, not just the destination. If you find something interesting along the way, don’t hesitate to take a detour or make an unplanned stop. Some of the best experiences happen off the beaten path.

Pack Essentials: Make sure your vehicle is in good condition, and pack essentials like a first aid kit, extra water, snacks, and a physical map. Cell service can be spotty in remote areas, so having a map is crucial.

Embrace the Nostalgia: Route 66 is steeped in history and nostalgia. Take time to explore the vintage motels, diners, and roadside attractions that have been preserved along the route. These places offer a glimpse into the past and are an integral part of the Route 66 experience.

Capture the Moments: Bring a good camera or use your smartphone to capture the sights along the way. Whether it’s a beautiful landscape, a quirky roadside attraction, or a historic landmark, Route 66 is full of photo-worthy moments.

Respect the Locals: Many of the towns along Route 66 are small, close-knit communities. Be respectful and courteous to the locals, and support local businesses whenever possible. Your patronage helps keep the spirit of Route 66 alive.

Enjoy the Journey: Finally, remember that Route 66 is all about the journey. Take your time, soak in the sights, and enjoy the unique experience of traveling America’s most famous road.

By following this Route 66 itinerary, you’ll make the most of your road trip adventure, creating memories that will last a lifetime. Whether you’re a seasoned road tripper or embarking on your first long drive, the Mother Road offers something for everyone. So, buckle up, hit the gas, and let Route 66 take you on the ultimate American road trip. Safe travels!