Few roads in the US inspire as much nostalgia as good old Route 66 leading from Chicago to Los Angeles. It represents western migration, freedom of the open road, the American spirit, and a sense of time gone by.

The road was first designated by the US Department of Public Roads in 1926, and after the Great Depression set in, it became a human river of westward moving farmers escaping the Dust Bowl.

WWII had its affect as well as the road was heavily used by the military convoys. Since it was an important road to the government at that time the road received some upgrades and widening.

Post WWII could be seen as Route 66’s heyday, with a surge in popularity. This is when the diners were established, the roadside attractions were created, and the motels multiplied.

By the mid 1950’s the road was getting to be in bad shape and was rerouted and bypassed by the new interstates coming through.

This leaves the question of how does one experience Route 66 today? It is no longer possible to do the trip using only the old road- some of it doesn’t even exist anymore!

If you have a limited amount of time it is not practical to try to stick to the old roads anyway. You can still experience the retro feeling of traveling across some of America’s most amazing cities and landscapes.

Here are eleven of today’s Route 66 highlights not to be missed…

1. Buckingham Fountain – Chicago, Illinois

Built in 1914, this large fountain is often considered the official starting point for Route 66 and is one of the most visited attractions in Chicago. On summer nights the fountain puts on a free show of music and colored lights.

2. Lincoln Home National Historic Site – Springfield, Illinois

Abraham Lincoln is one of the most famous presidents of US history, and Illinois is known as the “Land of Lincoln.” He is most known for signing the Emancipation Proclamation which declared that black slaves were free men and women.

3. Chain of Rocks Bridge – Saint Louis, Missouri

The bridge spans the mighty Mississippi River, connecting Illinois and Missouri. The bridge is now closed to motor vehicles, but is thrilling to cross by foot. It’s a great place to get views of the shoreline and the skyline of St. Louis.

4. Meramec Caverns – Stanton , Missouri

It is not technically on Route 66, but has been a popular side trip since the early days of the highway. Many people do not realize that Missouri is known as the Cave State and has over 6,000 caves within its borders, and Meramec Caverns are the largest among them.

5. Route 66 Museum – Clinton, Oklahoma

Learn everything you want to know and more at this roadside museum. They have been collecting memorabilia such as signs, pins, and posters for years, and recently received a half million dollar renovation.

Here you can also see displays on features of the highway that no longer exist today.

6. Devil’s Rope Museum – McLean, TX

Stopping at quirky, special interest museums along the way is a tradition of Route 66 road trips. In a converted factory, this small town Texas museum is dedicated to the history of barbed wire as well as a Texan tribute to the Mother Road.

7. Cadillac Ranch – Amarillo, Texas

A Route 66 “must-see” lies outside of Amarillo to the west. Constructed in 1974 by three artists, this public modern art installation has captured imaginations since.

It is a real eyebrow raiser, and the fact it’s in the middle of a cow pasture just adds to the surrealist aspect of it. Visitors are even encouraged to add their own spray paint.

8. Blue Hole – Santa Rosa, New Mexico

A trip down Route 66 in the summertime can be a hot one. Blue Hole offers some much needed relief. This is a deep spring popular with swimmers, snorkelers, and even scuba divers.

The deep blue water is a constant chilly 64 °F (18 °C) so it makes for a refreshing midday dip.

9. Petrified Forest National Park – Arizona

This national park combines several amazing features including the badlands of the Painted Desert and Blue Mesa, as well as prehistoric petroglyph sights.

Of course the main draw are the thousands of ancient petrified trees, the largest density of them anywhere on the earth. There are several hikes you can do through site of whimsical names such as Crystal Forest and Rainbow Forest.

10. Snow Cap Drive-In – Seligman, Arizona

Of all the funky, retro, and historic eateries on route, this drive-in has got to be one of the most well known ones. The menu is has a classic selection of burgers, hot dogs, and root beer floats. Be sure to check out Juan’s Garden behind the restaurant to see a collection of antique cars and other kitsch items. This is definitely a place with a sense of silly humor which has been a tradition in the family owned establishment since the beginning.

11. Santa Monica Pier – Los Angeles, California

The pier is considered the official end of Route 66. The pier itself is a bit like a carnival with an original 1920’s carousel and games, and the surrounding beach is a great place to take a load off.

If you are there on a Saturday, make a visit to the nearby Santa Monica Farmer’s Market to see the colourful array of produce and food items.

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About The Author

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Crystal got the itch to travel while living in Chicago in 2007 and hasn't turned back. Now she works in Alaska as a tour director during the summertime, and travels around the world and works odd jobs in the winters. She has also discovered a passion for helping others achieve their travel aspirations.