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Collector and Classic Car Insurance for Less

Route 66 – The Ultimate Classic Car Cruise

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Road Trip Made in the USA

Whether reading John Steinbeck’s The Grapes of Wrath, singing the classic song, watching the ultimate corvette road trip movie or memorizing the animated film Cars with your kids, the iconic U.S. Route 66 is still one of the best road trips to experience true Americana. This 2,448-mile roadway that runs from Chicago to Santa Monica is often referred to as the “Main Street of America,” and the sweet spot for a classic car enthusiast is to cruise it yourself.

Don’t Scoot and Shoot – Soak it In

As the locals say, don’t “scoot and shoot” by riding the Will Rogers Highway (another one of its nicknames), taking a selfie and moving on. A full trip that hits all the touristy highlights takes around two weeks. If you want to stop and experience the small town ambience, then you need an entire month.

The “Mother Road” West

The “Mother Road,” as Steinbeck calls it, opens in 1926 as a way to connect Chicago to Los Angeles and becomes the main artery for westward migration during the Dust Bowl of the 1930’s. Starting in Springfield, Illinois, it crosses three time zones and eight states (Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California) on its way west.

National Scenic Byway

Plan your trip without relying on GPS alone. Route 66 had all but vanished by the early 80’s due to the growth of interstate highways. Many portions of the highway are no longer around and road signs often go missing. Officially decommissioned in 1985, the few remaining sections have become a National Scenic Byway renamed the Historic Route 66. Guide books can help navigate you through the small towns and point out hidden treasures. 

Route 66 americas national scenic byway


Shaping the Way America Travels

From the simple two-pump filling stations in front of old houses to the sleek, modern ones with service bays and tire dealers, Route 66 helps shape car travel in America. Early motorists sleep in their cars on the side of the road and after WWII, they drive up to a comfortable motor lodge or motel at the end of a trip. Truck stops also dot the landscape; one of the oldest in America, the Dixie Truckers Home in McLean, Illinois (est. 1928) is still pumping gas and serving a delicious buffet.

Route 66 helped to shape car travel in america


10 Most Excellent Stops Along Route 66

  1. Lou Mitchell’s Restaurant (Chicago, IL) – Established in 1923 this eatery often gives out fresh donut holes and Milk Duds to its patrons.
  2. Chain of Rocks Bridge (Illinois-Missouri border) – Now a footbridge, it is part of the original Route 66 that spans the Mississippi River.
  3. Cars on Route (Galena, KS) – Formerly the Four Girls on Route service station, this landmark’s 1951 tow truck is the inspiration for the “Tow Mater” character in the film Cars.
  4. Oklahoma Route 66 Museum (Clinton, OK) – Everything you ever want to know about the road and then some.
  5. Cadillac Ranch (Amarillo, TX) – This is classic car art at its finest. Ten graffiti-covered Cadillacs buried nose first in the Texas dirt.
  6. U Drop Inn (Shamrock, TX) – A piece of green-tiled art deco architecture that many classic car buffs will recognize.
  7. Blue Swallow Motel (Tucumcari, NM) – It’s landmark neon sign still lights up the night sky as it welcomes weary travelers.
  8. Hackberry General Store (Hackberry, AZ) – Gas, groceries and a trip down memory lane, all in one place.
  9. Wigwam Motel (Holbrook, AZ) – One of the last three concrete teepee motels left in America. Others are in California and Kentucky.
  10. Santa Monica Pier (Santa Monica, CA) – Though the route ends a few blocks away, this is the picture perfect spot to end your journey.


Birthplace of Route 66 Festival August 12-14

Check out the Birthplace of Route 66 Festival August 12-14 in Springfield, Missouri to help plan your road trip to see a slice of American history along this storied highway that is sadly vanishing.

Collector and Classic Car Insurance for Less

Whether restoring a classic corvette or helping preserve a national treasure like Route 66, honoring our past is important to the collector car community. Classic Auto Insurance respects your commitment to staying true to your car’s history. There are no “one size fits all” policies here! Our friendly, knowledgeable staff will answer all your questions and find the right coverage for your classic. Visit our website at and see how we can help safeguard your dream car.

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