Table of Contents

• Route: Chicago, Springfield, St. Louis, Springfield, Amarillo, Santa Fe
• Highlights: Chain of Rocks Bridge, Cadillac Ranch, Petrified Forest National Park, Santa Fe Plaza
• Theme: Historic Adventure

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Introduction

Route 66, often referred to as the "Main Street of America," is more than just a road; it's a journey through the heart of the United States, steeped in history, culture, and nostalgia. Stretching from Chicago to Santa Fe and back, this "Historic Adventure" takes you through a kaleidoscope of landscapes, from the urban sprawl of the Midwest to the expansive deserts of the Southwest. As you traverse this iconic route, you'll encounter relics of a bygone era, quirky roadside attractions, and breathtaking natural wonders. Join William and Hui Cha Stanek on this historic adventure, as they share their personal insights and experiences, guiding you through the soul of America.

Personal Insights from Hui Cha Stanek: "Route 66 is a journey into the past, a road that echoes with the stories of countless travelers who have come before us. It's a path that winds through the heart of America, where the spirit of exploration and adventure is palpable at every turn. William and I have always been drawn to the history and romance of Route 66 - the neon signs, the vintage motels, and the endless stretches of open road that invite you to keep driving, to see what lies just beyond the horizon. This trip is not just about the destinations, but about the journey itself - the people you meet, the stories you hear, and the memories you make along the way. Route 66 is more than a road; it's a ribbon of memories that ties the past to the present, and we're excited to share this adventure with you."

Note: See our 11-Day Road Trip for return to Chicago or our Santa Fe to Los Angeles Road Trip to continue.

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Day 1: Chicago to Springfield, Illinois

Morning: Departure from Chicago

• Overview: Start your journey in the vibrant city of Chicago, the starting point of historic Route 66. Before hitting the road, take some time to explore a few of the city's iconic sites, like Millennium Park and Buckingham Fountain.
• Tips from Hui Cha: "Chicago is a city of contrasts - modern skyscrapers stand side by side with historic buildings. Capture the early morning light reflecting off the glass facades of the downtown skyline."

Mid-Morning: Joliet

• Overview: Head out of Chicago towards Joliet, known for its rich history and beautiful architecture. Stop by the Joliet Route 66 Welcome Center for a quick introduction to the road ahead.
• Recommended Scenic Stops: Joliet Historical Museum, Old Joliet Prison, Route 66 Raceway.
• Photography Tips: "The Route 66 sign at the Welcome Center is a must-capture moment to commemorate the start of your journey."

Lunch Stop: Joliet

• Lunch Recommendations:
  1. The Public Landing Restaurant: Enjoy American cuisine in a historic building overlooking the Des Plaines River.
  2. Old Fashioned Pancake House: A local favorite for hearty breakfasts and classic American diner fare.
  3. Hamburgerseria: A casual spot known for its creative burger options and relaxed atmosphere.

Afternoon: Route to Springfield

• Overview: Continue your journey southwest towards Springfield, the capital of Illinois and a city rich in Abraham Lincoln history.
• Recommended Scenic Stops: Route 66 Association Hall of Fame and Museum in Pontiac, Lincoln's Tomb, and the Old State Capitol in Springfield.
• Evening: Explore Springfield's historic downtown before settling in for the night.
• Dining Recommendations:
  1. D'Arcy's Pint: Known for their famous horseshoe sandwich, a Springfield specialty.
  2. Maldaner's Restaurant: A fine dining experience offering farm-to-table American cuisine.
  3. Cooper's Hawk Winery & Restaurant: A perfect spot for wine lovers, offering a wide selection of wines and a sophisticated menu.
• Accommodation Options:
  1. Inn at 835: A historic bed and breakfast offering elegant rooms and modern amenities.
  2. President Abraham Lincoln Springfield - a DoubleTree by Hilton: A comfortable stay with historic charm.
  3. Route 66 Hotel and Conference Center: A themed hotel offering a nostalgic experience along the famous route.

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Day 2: Springfield to St. Louis, Missouri

Morning: Explore Springfield

• Overview: Spend the morning exploring the historic sites of Springfield, including the Abraham Lincoln Presidential Library and Museum and Lincoln Home National Historic Site.
• Tips from Hui Cha: "Springfield is steeped in history. The Lincoln Home, in particular, offers a poignant glimpse into the life of one of America's greatest presidents. Early morning is the best time to visit to avoid crowds and capture the quiet dignity of the site."

Mid-Morning: Route to St. Louis

• Overview: Depart Springfield and continue your journey along Route 66 towards St. Louis.
• Recommended Scenic Stops: Chain of Rocks Bridge (a unique mile-long bridge crossing the Mississippi River), Henry's Rabbit Ranch, and the small town of Litchfield, known for the historic Ariston cafe.
• Photography Tips: "The Chain of Rocks Bridge offers a stunning view of the Mississippi River and the distant skyline of St. Louis. It's a fantastic spot for panoramic shots."

Lunch Stop: Litchfield

• Lunch Recommendations:
  1. Ariston cafe: A Route 66 landmark serving classic American dishes since 1924.
  2. Jubelt's Bakery & Restaurant: A family-owned spot offering homemade baked goods and comfort food.
  3. The Garden Family Restaurant: A casual eatery known for its friendly service and hearty meals.

Afternoon: Arrival in St. Louis

• Overview: Arrive in St. Louis, a city known for its iconic Gateway Arch and vibrant cultural scene. Spend the afternoon exploring the city's highlights.
• Recommended Scenic Stops: Gateway Arch, St. Louis Cathedral Basilica, and Forest Park.
• Evening: Enjoy an evening in St. Louis, sampling the city's famous barbecue and blues music.
• Dining Recommendations:
  1. Pappy's Smokehouse: A must-visit for Memphis-style barbecue.
  2. Sidney Street cafe: A fine dining experience with creative New American cuisine.
  3. Blues City Deli: A lively spot combining great sandwiches with live blues music.
• Accommodation Options:
  1. The Chase Park Plaza Royal Sonesta St. Louis: A luxurious hotel located in the heart of the city.
  2. The Moonrise Hotel: A boutique hotel with a funky, space-themed decor and rooftop bar.
  3. Hotel Saint Louis, Autograph Collection: A historic hotel offering modern luxury and a central location.

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Day 3: St. Louis to Springfield, Missouri

Morning: Explore St. Louis

• Overview: Begin your day by visiting some of St. Louis's most iconic sites, including the Gateway Arch and the Old Courthouse.
• Tips from Hui Cha: "The Gateway Arch is a symbol of westward expansion and offers incredible views of the city and the Mississippi River. The morning light is perfect for capturing the Arch's gleaming exterior."

Mid-Morning: Route to Springfield, Missouri

• Overview: Depart St. Louis and continue your journey through Missouri, heading towards Springfield.
• Recommended Scenic Stops: Meramec Caverns (a large cave system with guided tours), the historic town of Cuba (known for its murals), and the Devil's Elbow (a picturesque bend in the road along the Big Piney River).
• Photography Tips: "The Meramec Caverns offer fascinating opportunities for low-light photography. Bring a tripod and explore the play of light and shadow in the cave formations."

Lunch Stop: Rolla

• Lunch Recommendations:
  1. Alex's Pizza Palace: A local favorite known for its Greek-style pizza and casual atmosphere.
  2. Bandana's Bar-B-Q: A regional chain serving up hearty, smoky barbecue.
  3. A Slice of Pie: Famous for its homemade pies, this cozy spot also offers sandwiches and soups.

Afternoon: Arrival in Springfield, Missouri

• Overview: Arrive in Springfield, Missouri, known as the birthplace of Route 66. Spend the afternoon visiting the Route 66 Car Museum and exploring the city's vibrant downtown.
• Recommended Scenic Stops: Route 66 Car Museum, Fantastic Caverns (America's only ride-through cave), and the Springfield Conservation Nature Center.
• Evening: Enjoy a relaxing evening in Springfield with a hearty meal and some local entertainment.
• Dining Recommendations:
  1. Gilardi's Ristorante: An Italian restaurant offering fresh, locally sourced dishes.
  2. Aviary cafe: Known for its savory and sweet crepes, this cafe has a charming, French-inspired ambiance.
  3. Black Sheep Burgers & Shakes: A popular spot for gourmet burgers and creative milkshakes.
• Accommodation Options:
  1. Hotel Vandivort: A chic, boutique hotel located in downtown Springfield.
  2. The Mansion at Elfindale: A historic bed and breakfast offering Victorian-style accommodations.
  3. Best Western Route 66 Rail Haven: A nostalgic, Route 66-themed motel with vintage flair.

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Day 4: Springfield, Missouri to Amarillo, Texas

Morning: Departure from Springfield, Missouri

• Overview: Begin your day with a hearty breakfast before heading southwest towards the vast landscapes of the Texas Panhandle.
• Tips from Hui Cha: "As you drive through Missouri, take time to appreciate the changing scenery - from the rolling hills to the flat plains as you approach the Southwest."

Mid-Morning: Route to Joplin

• Overview: Pass through the town of Joplin, Missouri, a city with deep ties to Route 66 history.
• Recommended Scenic Stops: Joplin's Route 66 Mural Park, Red Oak II (a recreated 1930s town), and the historic Boots Court Motel in Carthage.
• Photography Tips: "Red Oak II is a photographer's playground - capture the nostalgia of a small-town America that feels frozen in time."

Lunch Stop: Tulsa, Oklahoma

• Lunch Recommendations:
  1. Elote cafe & Catering: A vibrant spot offering fresh Mexican-inspired dishes.
  2. Mother Road Market: A food hall with various vendors, perfect for sampling different cuisines.
  3. The Tavern: A gastropub known for its creative comfort food and cozy atmosphere.

Afternoon: Route to Amarillo, Texas

• Overview: Continue your journey through Oklahoma, crossing into the Texas Panhandle, and heading towards Amarillo.
• Recommended Scenic Stops: The Blue Whale of Catoosa (a quirky roadside attraction), the Oklahoma Route 66 Museum in Clinton, and the U-Drop Inn in Shamrock (an art deco gas station and cafe).
• Evening: Arrive in Amarillo, known for its wide-open spaces and Texas charm.
• Dining Recommendations:
  1. The Big Texan Steak Ranch: Famous for its 72-ounce steak challenge and classic Texas ambiance.
  2. Coyote Bluff cafe: A laid-back spot offering some of the best burgers in Texas.
  3. Youngblood's cafe: Known for its down-home cooking and hearty portions.
• Accommodation Options:
  1. The Big Texan Motel: A themed motel offering a true Texas experience, complete with western decor.
  2. Embassy Suites Amarillo Downtown: Modern accommodations with spacious suites and a convenient location.
  3. Courtyard by Marriott Amarillo Downtown: A historic hotel located in the heart of Amarillo, blending modern comfort with historic charm.

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Day 5: Amarillo to Santa Fe, New Mexico

Morning: Departure from Amarillo

• Overview: Start your day with a visit to one of Route 66's most iconic landmarks, Cadillac Ranch, before heading west towards New Mexico.
• Tips from Hui Cha: "Cadillac Ranch is a must-see - these half-buried cars covered in graffiti are a symbol of Route 66's quirky charm. Don't forget to bring your own spray paint to leave your mark."

Mid-Morning: Route to Tucumcari, New Mexico

• Overview: Continue your journey along Route 66, crossing into New Mexico, and heading towards the town of Tucumcari, known for its vibrant murals and classic motels.
• Recommended Scenic Stops: Cadillac Ranch, Midpoint cafe in Adrian (the exact midpoint of Route 66), and Tucumcari's Blue Swallow Motel (one of the most iconic motels on Route 66).
• Photography Tips: "Tucumcari's murals and neon signs are a photographer's dream - capture the vintage vibe in the early evening when the neon starts to glow."

Lunch Stop: Tucumcari

• Lunch Recommendations:
  1. Kix on 66: A retro diner offering classic American breakfast and lunch options.
  2. Del's Restaurant: A long-standing Route 66 establishment known for its comfort food and friendly service.
  3. Pow Wow Restaurant & Lizard Lounge: A quirky spot with Southwestern dishes and a lively atmosphere.

Afternoon: Route to Santa Fe

• Overview: Continue your journey through the high deserts of New Mexico towards Santa Fe, a city known for its rich history, arts, and unique blend of Native American and Spanish cultures.
• Recommended Scenic Stops: Santa Rosa (Blue Hole, a natural swimming hole), Pecos National Historical Park (ancient pueblo ruins), and Glorieta Pass.
• Evening: Arrive in Santa Fe, where you can explore the city's historic plaza and vibrant arts scene.
• Dining Recommendations:
  1. The Shed: A Santa Fe institution serving traditional New Mexican cuisine.
  2. Geronimo: An upscale dining experience offering global flavors with a Southwestern twist.
  3. Coyote cafe: A creative, contemporary take on Southwestern cuisine.
• Accommodation Options:
  1. Inn of the Governors: A charming hotel offering Southwestern hospitality and authentic decor.
  2. La Fonda on the Plaza: A historic hotel located on Santa Fe's famous plaza, blending luxury with history.
  3. The Inn & Spa at Loretto: A luxurious retreat offering a unique adobe-style architecture and world-class amenities.

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Day 6: Explore Santa Fe, New Mexico

Morning: Explore Santa Fe

• Overview: Spend the day immersing yourself in the rich cultural heritage of Santa Fe, from its art galleries to its historic landmarks.
• Tips from Hui Cha: "Santa Fe is a city that celebrates its history and culture - spend time exploring the Santa Fe Plaza, visiting the Georgia O'Keeffe Museum, and strolling through the many art galleries on Canyon Road."

Mid-Morning: Santa Fe Plaza and Surroundings

• Overview: Start your day at the Santa Fe Plaza, the heart of the city, surrounded by historic buildings and museums.
• Recommended Scenic Stops: Santa Fe Plaza, Palace of the Governors, Loretto Chapel (famous for its miraculous staircase), and the Cathedral Basilica of St. Francis of Assisi.
• Photography Tips: "The Plaza and surrounding areas are rich in history - capture the adobe architecture and the vibrant colors of the local markets."

Lunch Stop: Santa Fe

• Lunch Recommendations:
  1. Cafe Pasqual's: A beloved eatery offering organic, locally-sourced dishes with a New Mexican flair.
  2. Tia Sophia's: Known for its classic New Mexican breakfast and lunch offerings, including the famous breakfast burrito.
  3. Palacio cafe: A cozy spot offering a mix of Southwestern and American dishes.

Afternoon: Canyon Road

• Overview: Spend the afternoon exploring Canyon Road, home to over 100 art galleries featuring works ranging from contemporary to traditional Native American art.
• Recommended Scenic Stops: Canyon Road Galleries, Museum of International Folk Art, and the Wheelwright Museum of the American Indian.
• Evening: Enjoy a final evening in Santa Fe, soaking in the unique blend of cultures that make this city so special.
• Dining Recommendations:
  1. La Choza: A local favorite offering authentic New Mexican dishes in a relaxed setting.
  2. Sazon: An upscale restaurant known for its innovative take on traditional Mexican cuisine.
  3. El Farol: A historic tapas restaurant offering live music and flamenco performances.
• Accommodation Options:
  1. Rosewood Inn of the Anasazi: A luxury boutique hotel that blends Southwestern style with modern comforts.
  2. Hotel Santa Fe: The city's only Native American-owned hotel, offering a unique cultural experience.
  3. La Posada de Santa Fe: A historic resort and spa located just steps from the Plaza.

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Conclusion

Reflections from Hui Cha Stanek:
"Route 66 is more than just a road - it's a journey through America's past, a path that weaves together the stories, dreams, and adventures of countless travelers. As we traveled from the skyscrapers of Chicago to the adobe houses of Santa Fe, I was reminded of the diversity and richness of our country. Each town, each stop, offered a glimpse into a different time, a different way of life. The road itself seemed to carry the echoes of those who had come before, from the pioneers seeking new opportunities in the West to the families on vacation in the golden age of the American road trip. As we made our way back, retracing our steps along this historic route, I couldn't help but feel a deep connection to those who had traveled this road before us. Route 66 is not just about the destinations, but about the journey itself - about the stories that are written with every mile, every turn, every stop. It's a reminder that while the road ahead may be uncertain, the journey is always worth taking."

Road Trip Music Recommendations for Route 66: "Historic Adventure"

Music is the perfect companion for a journey along the historic Route 66, setting the tone as you travel from the bustling streets of Chicago to the artistic hub of Santa Fe. Each playlist is tailored to different age groups, capturing the spirit of adventure, nostalgia, and the diverse landscapes you'll encounter along the way.

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For Adults 20-35

This playlist blends modern hits with indie and alternative tracks that evoke the sense of freedom and exploration that comes with a road trip on Route 66.

1. "Take Me Home, Country Roads" by John Denver - A classic road trip anthem that's perfect for wide-open spaces.
2. "Home" by Edward Sharpe & The Magnetic Zeros - A feel-good indie hit that celebrates the journey and the people you share it with.
3. "Ho Hey" by The Lumineers - A catchy folk-rock tune that's great for singing along as you drive.
4. "Midnight City" by M83 - An atmospheric, synth-driven track that matches the open roads and endless skies.
5. "Drive" by Incubus - A reflective rock song that pairs well with the vast landscapes of the Midwest and Southwest.
6. "Send Me on My Way" by Rusted Root - An upbeat, rhythmic song that captures the joy of the journey.
7. "Road Trippin'" by Red Hot Chili Peppers - A mellow, acoustic track that's all about the freedom of the open road.
8. "Ain't No Rest for the Wicked" by Cage the Elephant - A gritty rock track with a rebellious spirit, perfect for Route 66's quirky roadside attractions.
9. "Life Is a Highway" by Tom Cochrane - A road trip classic that's synonymous with long drives and adventure.
10. "Riptide" by Vance Joy - A laid-back indie-folk song that fits the easy-going pace of a cross-country drive.
11. "Ophelia" by The Lumineers - A modern folk-rock track with an infectious chorus, ideal for cruising along Route 66.
12. "Electric Feel" by MGMT - A psychedelic pop tune that adds a touch of fun and excitement to your journey.

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For Adults 35-50

This playlist mixes 90s and 2000s rock with Americana and classic tracks that echo the historic and adventurous spirit of Route 66.

1. "Born to Run" by Bruce Springsteen - An iconic rock anthem that embodies the spirit of freedom and the open road.
2. "Iris" by Goo Goo Dolls - A powerful ballad that pairs well with the sweeping landscapes of the Midwest.
3. "Learning to Fly" by Tom Petty and the Heartbreakers - A reflective track that captures the feeling of being on a journey.
4. "Fast Car" by Tracy Chapman - A soulful, introspective song about the desire for a better life, fitting for a road steeped in history.
5. "Where the Streets Have No Name" by U2 - A soaring anthem perfect for the wide-open spaces of the Southwest.
6. "Runaway Train" by Soul Asylum - A 90s classic that adds a touch of nostalgia to your drive.
7. "Santa Monica" by Everclear - A rock track that celebrates California dreaming, ideal as you approach the end of the route.
8. "One Headlight" by The Wallflowers - A mid-90s hit that's perfect for night driving and reflecting on the road ahead.
9. "Interstate Love Song" by Stone Temple Pilots - A rock track that captures the essence of traveling down the highway.
10. "Counting Blue Cars" by Dishwalla - A 90s alternative rock hit with a laid-back vibe, perfect for cruising.
11. "What I Got" by Sublime - A feel-good track with a relaxed, carefree energy that suits the journey.
12. "The Way" by Fastball - A mysterious, yet catchy song that fits the adventurous spirit of Route 66.

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For Adults 50+

This playlist features timeless classics, rock, and folk tunes that evoke nostalgia and the historic charm of Route 66.

1. "Route 66" by Nat King Cole - The ultimate Route 66 anthem, setting the perfect tone for your historic adventure.
2. "On the Road Again" by Willie Nelson - A country classic that celebrates the joy of hitting the open road.
3. "Take It Easy" by Eagles - A laid-back rock track that's perfect for the wide-open roads of the Southwest.
4. "King of the Road" by Roger Miller - A cheerful, carefree tune that embodies the spirit of the traveler.
5. "Ramblin' Man" by The Allman Brothers Band - A Southern rock classic that fits the journey through the heart of America.
6. "Mustang Sally" by Wilson Pickett - A soulful track that adds a bit of groove to your drive.
7. "The Weight" by The Band - A folk-rock classic that's ideal for reflecting on the journey.
8. "California Dreamin'" by The Mamas & The Papas - A nostalgic track that captures the allure of the West Coast.
9. "Me and Bobby McGee" by Janis Joplin - A soulful, road-trip classic with themes of freedom and adventure.
10. "Sweet Home Alabama" by Lynyrd Skynyrd - A Southern rock anthem that pairs well with the Southern stretches of Route 66.
11. "The Wanderer" by Dion - A rock 'n' roll classic that's all about the spirit of adventure.
12. "(Sittin' On) The Dock of the Bay" by Otis Redding - A soulful tune that's perfect for moments of quiet reflection along the route.

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These playlists are designed to complement the journey along Route 66, capturing the spirit of the open road, the history, and the sense of adventure that makes this road trip so special. Whether you're soaking in the nostalgia of the past or embracing the excitement of discovery, these songs will enhance your experience and create lasting memories on your Historic Adventure.