The Classic American Road Trip: Celebrating the Iconic History of Route 66

Route 66 inspired the first great American road trip. As its centenary is approaching, America’s National Trust for Historic Preservation is collecting personal memories and photos from tourists and travelers to compile a comprehensive account of the Mother Road’s history. In this post, we’ll visit some of the legendary highway’s iconic stops.

Nothing beats a classic American road trip, where you hit the road, explore the open country, and see a part of America you thought was long gone. One of the world’s most iconic road trips, at least in the Northern Hemisphere, is Route 66. This historic highway has risen to celebrity status and is a bucket list road trip for travelers in no particular hurry.   

winslow arizona route 66 sign
Route 66 sign in Winslow, Arizona

Route 66: General Overview

U.S. Route 66 is a little over 2,400 miles long. Driving from Illinois to California is a great way to immerse yourself in the highway’s rich history and discover America’s heartland as Route 66 passes through iconic towns and cities in eight states. 

After a stay in the Windy City, you’ll head to Springfield, Missouri. From here, you can travel along one of the best-preserved sections of Route 66 to Tulsa and then further west to Albuquerque in New Mexico and Flagstaff, Arizona

All these cities offer visitors a chance to see iconic and historic sights, including a collection of classic cars, beautiful Art Deco buildings, and the legendary bar and motel neon signs that help to tell the colorful story of Route 66 since its opening almost a hundred years ago.

Driving From Route 66 Official Starting Point to its Ceremonial Birthplace

If you’re driving the entire length of Route 66 from east to west, a versatile crossover offers comfort and fuel efficiency on the long stretches of open road. With stopovers along the way, you’ll also want a car that’s easier to drive in the city than other larger SUVs, especially when you’re navigating through the streets of Chicago to reach the official Route 66 starting point on Michigan Avenue. 

Before setting off on your trip, check out the view from America’s highest observation platform, Skydeck Chicago, where you can see as far as 50 miles along Route 66. Once on the road, you’ll reach Springfield, Missouri, after just over 500 miles of driving. The city is known as the birthplace of Route 66, as this is where the highway was officially named in 1926.  

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Among the many sights to see in Springfield, car enthusiasts will enjoy the Route 66 Car Museum, home to over 70 vintage car models, many of which would have been on the road when the route was first opened. More motoring memorabilia is on show at the iconic Best Western Rail Haven Motel, where vintage gas pumps flank the motel’s office, and in the Elvis Presley Suite, you can sleep in a bed shaped like a Cadillac.

Route 66
Antique cars and gas station along Route 66

Art Deco Treasures in the Heart of the Route’s New Official Capital

From Springfield, keep heading west to Tulsa, Oklahoma, the city that has recently secured the U.S. copyright as the official capital of Route 66. With Gateway Arches at either end, a 28-mile stretch of the famous highway runs through the city and will take you past some of America’s most impressive examples of Art Deco architecture. 

Built in 1924 as a Route 66 filling station, the iconic Blue Dome resembles the Hagia Sophia mosque in Istanbul and is now at the center of a vibrant arts district offering a wide range of shops, restaurants, and nightlife. Other Art Deco treasures can be found in Tulsarama Town Square on Route 66 and the downtown Deco District, with one of the most notable buildings, the Boston Avenue Methodist Church, situated a little further south. 

Route 66
Old gas station along Route 66

Vintage Neon Signs in Albuquerque and Flagstaff

After another ten hours of driving, you’ll reach Albuquerque, a city with a long-standing relationship with Route 66, as the road runs right through it past distinctive shops and unique restaurants. In honor of the upcoming 100th anniversary of the ‘Mother Road’ and with the help of the City of Albuquerque, several local businesses are restoring the vintage neon signs of their iconic premises. The City Council has also proposed a welcome gateway on the city’s east side to match the sign already in place in the west. 

For more iconic neon signs, follow the road further west to Flagstaff in Arizona, the highest point of Route 66. Just over 14 miles of the historic road remain in the city, and an urban trail following part of the historic route allows visitors to walk along a segment of the route’s 1939 pavement. Look out for landmark neon signs of the Western Hills Motel and the world-famous Museum Club, a roadhouse and dance hall offering some of the best live country and western music.

Route 66
Route 66 near Flagstaff

The approaching centenary of Route 66 has created renewed interest in recording the highway’s history and restoring some of its iconic features. You can become a part of the route’s story on a classic American road trip that takes in some of the historic features of major cities along the road.