Route 66 Check-in Challenge

Embarking on a journey along Route 66 is like traveling through a living museum of Americana. From the bustling streets of Chicago to the surf-soaked piers of Santa Monica, this iconic highway stitches together a vibrant tapestry of American history, culture, and natural beauty. Every turn of the wheel brings you face-to-face with quirky roadside attractions, charming diners, and awe-inspiring landscapes—all of which belong on any Route 66 bucket list. Whether you're a history buff, a foodie, or an adventure seeker, there's something magical waiting for you on the Mother Road. So buckle up and get ready to explore the best things to do along Route 66, where every mile is a story waiting to be told.

Historic Route 66 sign, Dell Rhea's Chicken Basket, The Berghoff Restaurant, Lou Mitchell's, Gateway Arch National Park, Milk Bottle Grocery, Arcadia Round Barn, Munger Moss Motel, Meramec Caverns, 66 Drive-In Theatre, Route 66 Auto Museum, Route 66 State Park, U Drop Inn Cafe, Route 66 Mother Road Museum, First Route 66 Sign in Illinois, Cozy Dog Drive In, Old Chain of Rocks Bridge Parking, Blue Swallow Motel, Cadillac Ranch, Gemini Giant

• Historic Route 66 sign, United States

  
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• Dell Rhea's Chicken Basket, United States

  
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• The Berghoff Restaurant in Chicago, United States

  
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  Nestled in Chicago, The Berghoff Restaurant is a historic gem that should not be missed on any Route 66 bucket list. Serving hearty German-American cuisine since 1898, this iconic establishment offers travelers a taste of rich tradition and a chance to experience a piece of Chicago's culinary history. As you embark on your Route 66 journey, a meal at The Berghoff provides the perfect blend of culture and classic flavors to kickstart your adventure.

• Lou Mitchell's in Chicago, United States

  
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  Lou Mitchell's in Chicago is a quintessential stop when embarking on a Route 66 adventure. Known as the "gateway to the Mother Road," this historic diner has been serving hearty breakfasts and complimentary Milk Duds to travelers since 1923. Starting your journey here will immerse you in a true slice of American hospitality and culinary tradition.

• Gateway Arch National Park in St. Louis, United States

  
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  Gateway Arch National Park in St. Louis is a must-visit landmark on your Route 66 bucket list, symbolizing the gateway to the West. The iconic 630-foot stainless steel arch offers breathtaking views of the Mississippi River and the city, and provides a fascinating history lesson at its museum focused on America's westward expansion. Don't miss the opportunity to take a tram ride to the top for a truly unforgettable experience.

• Milk Bottle Grocery in Oklahoma City, United States

  
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  Milk Bottle Grocery, a quirky and iconic pit stop along Route 66, features a giant milk bottle on its roof, making it a must-see for travelers seeking unique roadside attractions. Located in Oklahoma City, this charming slice of Americana captures the nostalgic spirit of the Mother Road and offers a perfect photo opportunity for those checking off their Route 66 bucket list.

• Arcadia Round Barn, United States

  
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  Nestled along the iconic Route 66, the Arcadia Round Barn is a must-see landmark renowned for its unique circular architecture and rich history dating back to 1898. As one of the best stops on the Route 66 bucket list, this meticulously restored barn offers visitors a glimpse into America's past, making it an essential experience for road trippers and history enthusiasts alike.

• Munger Moss Motel, United States

  
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  The Munger Moss Motel in Lebanon, Missouri, is a quintessential stop on the Route 66 bucket list, embodying the nostalgic charm of the historic Mother Road. Established in 1946, this motel offers vintage accommodations that transport travelers back in time, complete with neon signs and period decor, making it a beloved landmark for Route 66 enthusiasts.

• Meramec Caverns, United States

  
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  Meramec Caverns, nestled in Stanton, Missouri, is a must-see wonder along Route 66, boasting stunning geological formations and rich history that dates back to pre-Columbian times. Once a reputed hideout for outlaw Jesse James, these expansive caverns now offer guided tours that reveal their spectacular stalactites, stalagmites, and dramatic underground features. Adding this natural attraction to your Route 66 bucket list promises a memorable blend of adventure and exploration.

• 66 Drive-In Theatre, United States

  
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  The 66 Drive-In Theatre in Carthage, Missouri, is a nostalgic gem that takes visitors back to the golden age of American road trips and cinema, making it a must-see stop on any Route 66 bucket list. Opened in 1949, this beautifully preserved drive-in still screens double features, allowing travelers to experience classic movie magic under the stars.

• Route 66 Auto Museum, United States

  
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  The Route 66 Auto Museum in Santa Rosa, New Mexico, is a must-see for car enthusiasts traveling the historic Route 66. Featuring over 30 classic and vintage cars, along with an impressive collection of Route 66 memorabilia, the museum offers a nostalgic journey back to the golden age of American road trips. It's an essential stop for anyone looking to fully immerse themselves in the rich automotive history that defines the iconic Mother Road.

• Route 66 State Park, United States

  
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  Route 66 State Park in Missouri is a must-visit spot on any Route 66 bucket list, offering a blend of history and natural beauty. Set on the grounds of the former town of Times Beach, the park features a visitor center with fascinating exhibits about the iconic highway's legacy and the unique story of the town's unexpected transformation. Outdoor enthusiasts can also enjoy picturesque trails, picnic areas, and river views, making it an ideal stop for both history buffs and nature lovers.

• U Drop Inn Cafe, United States

  
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  A visit to Route 66 would be incomplete without stopping at the iconic U Drop Inn Café in Shamrock, Texas. This historic Art Deco building, originally constructed in 1936, now serves as a visitor center and museum, offering a nostalgic glimpse into the golden era of America's "Mother Road." With its unique architecture and charming ambiance, it's a must-see destination for any Route 66 enthusiast.

• Route 66 Mother Road Museum, United States

  
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  The Route 66 Mother Road Museum in Barstow, California, is a must-visit stop on any Route 66 bucket list, offering a treasure trove of memorabilia and exhibits that celebrate the iconic highway's rich history. Showcasing vintage cars, photographs, and artifacts, the museum provides a nostalgic journey through time, making it a perfect destination for history buffs and road trip enthusiasts alike.

• First Route 66 Sign in Illinois in Chicago, United States

  
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  A must-see stop on your Route 66 bucket list is the First Route 66 Sign in Illinois, located in downtown Chicago at the historic intersection of Adams Street and Michigan Avenue. This iconic sign marks the eastern terminus of the legendary Mother Road, inviting travelers to begin their journey with a photo op and a sense of nostalgia for the epic adventure ahead. Starting your Route 66 journey here sets the tone for the American road trip experience, filled with historic landmarks, quirky roadside attractions, and unforgettable memories.

• Cozy Dog Drive In in Springfield, United States

  
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  Cozy Dog Drive In in Springfield, Illinois, is a must-visit spot along Route 66 for anyone creating a bucket list of iconic stops. Famous for inventing the corn dog on a stick, this nostalgic eatery offers both a delicious taste of Americana and a genuine glimpse into the roadside charm that makes Route 66 legendary. Make sure to grab a Cozy Dog and take in the vibrant Route 66 memorabilia that adorn the walls.

• Old Chain of Rocks Bridge Parking in Granite City, United States

  
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  The Old Chain of Rocks Bridge Parking is a must-stop on your Route 66 bucket list, offering easy access to one of the most iconic pedestrian bridges along the historic highway. Originally part of the "Mother Road," the bridge spans the Mississippi River and provides a scenic, nostalgic walk with stunning views, making it a perfect spot for photos and reflection on the journey's past. Be sure to allocate some time to explore the retro charm and learn about its historical significance.

• Blue Swallow Motel in Tucumcari, United States

  
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  The Blue Swallow Motel in Tucumcari, New Mexico, is a quintessential stop on any Route 66 bucket list. This historic motor court, with its retro neon sign and charmingly preserved rooms, offers a nostalgic glimpse into the golden age of American road travel. Staying here provides an authentic experience that embodies the spirit of the Mother Road.

• Cadillac Ranch in Amarillo, United States

  
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  Cadillac Ranch in Amarillo, Texas, is a must-see stop along Route 66, where ten vibrant, graffiti-covered Cadillacs are half-buried nose-first in the ground. This iconic public art installation invites travelers to contribute their own spray-painted designs, making it a living canvas and a unique, interactive experience on your Route 66 journey. Don't forget to bring some spray paint and leave your mark on this quirky and colorful landmark.

• Gemini Giant, United States

  
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  The Gemini Giant is a must-see attraction on the Route 66 Bucket List, embodying the nostalgic spirit of America's historic highway. Located in Wilmington, Illinois, this 28-foot tall fiberglass statue of a spaceman, donning a space helmet and holding a rocket, serves as a whimsical roadside photo op and a tribute to mid-20th-century American car culture. It's a perfect stop to capture a piece of classic Americana along your Route 66 journey.