The 10 Best Documentaries And Videos About Route 66

Sep 29, 2023 | Best Of, Geography

Route 66 is one of the most iconic roads in America, and it has been immortalized countless times through books, films and television shows. Now, its story can be told through documentaries as well! The best documentaries about Route 66 showcase the winding road’s intriguing history and alluring charm. From exploring the old-fashioned diners along its length to uncovering the secrets of its wild past, these documentaries provide an in-depth look at one of America’s most beloved highways. Here are some of the best documentaries about Route 66 that you won’t want to miss!


1. Route 66: The Road Into America’s Heartlands

Route 66 has been a long-time symbol of Americana, and for good reason. This celebrated highway has served as the main artery connecting all parts of the country since 1926. Over its storied history, Route 66 has seen travelers from all walks of life: families on vacation, bikers out to explore the open road, and everyone in between. The road has provided a gateway to adventure, travel, and exploration for millions of people over the years. Now, with documentaries like “Route 66


2. The Rise and Fall of Route 66 (Why America’s Greatest Road Fell into Oblivion)

Route 66 is no ordinary highway – it’s a symbol of America’s history, culture and identity. It was the first ever highway built in the United States and has spanned over 90 years, with plenty of decades-worth of weird stops and attractions along its iconic route from Chicago to Los Angeles. This road less traveled has seen many changes since its inception in 1926, but it was ultimately decommissioned as a major highway in 1985. While large chunks of the original Route 66 have now vanished, its legacy lives on through the amazing artifacts and memorabilia kept at the Route 66 Association Hall of Fame and Museum.


3. Revive Route 66 – A Roadmovie Documentary.

Few roads in the US have seen more history, adventure and tragedy than Route 66. From the Dust Bowl refugees of the 1930s to today’s modern travelers, many people have made their way along this historic highway. Revive Route 66 – A Roadmovie Documentary captures this iconic route with a unique combination of music, interviews and stunning photography.The documentary follows several different travelers as they make their way along the Mother Road.


4. Chicago: The Birth of the Legendary Route 66

Route 66 – the Legendary Journey Across America. It’s a journey that started almost 80 years ago, when it connected Chicago to Los Angeles across eight states and four time zones. Today, it’s an iconic symbol of American history and culture – a nostalgic drive through some of its most dramatic moments. From the bustling streets of Chicago to wide open deserts in California, Route 66 is a time capsule of America at its best. Whether it’s the unique diners, quirky roadside attractions and vintage motels or simply the joy of listening to classic American music on a long drive, Route 66 takes you back in time.


5. Route 66: Main Street America

Route 66: A Journey Into America’s Past. This epic documentary from The Learning Channel explores the history of the iconic American highway. Viewers can follow its meandering path from Illinois to California, understanding how it has connected people and places for generations. Along the way, they’ll learn about roadside attractions like City Hall in Amarillo, Texas, as well as the stories of the people who lived, traveled and worked on Route 66. A must-see for those interested in American culture and history!


6. Route 66 Road Trip: Everything To Do & See

Looking to get the most out of your Route 66 road trip? You’re in luck! We’ve traveled the entire length of Route 66 and we want to share our experiences with you. From the desert roads of Arizona, to the classic neon signs in Oklahoma, let us guide you through all that’s worth seeing along this iconic highway. Discover mind-blowing vistas, historic parks and monuments, bustling cities and more! It’s time to get ready for the adventure of a lifetime on Route 66. Get your maps ready and buckle up – you won’t want to miss a single thing!


7. Billy Connolly Travel’s Across America’s Most Famous Road | Route 66 E1

Take a journey with Billy Connolly as he travels along America’s legendary Route 66. From the desert landscapes of Arizona to the bustling city of Chicago, explore the famous roads and landmarks that have made this route legendary. Along the way, discover hidden gems from forgotten diners and roadside attractions; find out about the unique people who call this part of America home; and laugh your way through some of the funniest moments from his adventures. Join Billy Connolly as he shows you why Route 66 is more than a road: it’s an American experience unlike any other.


8. Route 66 Road Trip: 14 Days Driving the Main Street of America

Exploring the legendary Route 66 is an experience like none other. A journey down this historic highway will take you from Santa Monica, California to Chicago, Illinois – a total of 2,400 miles. Taking 14 days to drive the entire route provides the perfect opportunity to explore small towns and cities along the way, uncovering hidden gems that evoke nostalgia for a bygone era.


9. ROUTE 66 1985

ROUTE 66 1985 takes viewers back to the days of Route 66 before it was decommissioned. This documentary gives an authentic look at the old highway, capturing the nostalgia that only a road trip down this iconic stretch of Americana can bring. From small towns and roadside attractions to larger cities along the way, audiences are treated to a glimpse into what it was like to journey down this legendary highway before it became a relic of the past. With interviews from local residents and experts on the history of Route 66, viewers can expect an eye-opening experience that will leave them with a newfound appreciation for this landmark highway.


10. A Journey Down Route 66

Take a wild ride down America’s iconic Route 66! From Chicago to Amarillo, we’ll explore the hidden gems that make up this iconic highway. You’ll visit one of the first truck stops in the business, sample amazing food at diners along the way, and learn why they called it “Bloody 66”. We’ll also drive past the Cadillac Ranch, take on a 72oz steak challenge, and see the Grand Canyon in all its beauty. On top of that, don’t forget to join the classic car “Fun Run” for an experience you won’t soon forget! Join us now on Route 66 – you won’t regret it!

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David B