Once dubbed America's Main Street, Route 66 was officially retired on June 27, 1985. Despite this, it still attracts countless travelers seeking a slice of nostalgia. If you're a fan of warm hospitality, charming small towns, and rich history, Route 66 is a journey worth taking. Below, we highlight some of the most intriguing spots along the iconic route. Feel free to share your own Route 66 adventures in the comments below.
10. Gemini Giant Located in Wilmington, Illinois

At the Launching Pad Drive-in, you'll find a towering 20-foot-tall green astronaut, complete with a rocket in hand, keeping watch over the area.
9. Dixie Truckers Home McLean, Illinois

Dixie Truckers Home holds the title of the oldest truck stop along Route 66. For nearly 70 years, it has only closed once—due to a fire. Today, it still provides travelers with food, fuel, and a small museum dedicated to the history of Route 66.
8. Chain of Rocks Bridge St. Louis, Missouri

The Chain of Rocks Bridge once spanned Route 66 over the grand Mississippi River. This bridge was distinctive due to its 24-degree curve in the middle, designed to allow boats to navigate the river. Eventually, the construction of I-270 rendered the bridge obsolete, and it was left in a state of neglect for years. However, it was later repurposed as a scenic path for pedestrians and cyclists. Nearby, two charming water intake towers rise above the river like miniature castles.
7. Ted Drewe’s Frozen Custard St. Louis, Missouri

If I had to choose only one dessert for the rest of my life, it would undoubtedly be Ted Drewe’s Frozen Custard. It is simply INCREDIBLE!
6. Meramec Caverns Stanton, Missouri

The infamous outlaw Jesse James used this cave system as a hideout, evading the sheriff's grasp. Eventually, the cave was transformed into a tourist attraction, and it's also where the iconic bumper sticker was first created!
5. The Blue Whale Catoosa, Oklahoma

Hugh Davis constructed The Blue Whale as a special anniversary present for his wife. Initially meant for private family use, the whale soon became a beloved swimming spot for both locals and tourists alike.
4. Cadillac Ranch Amarillo, Texas

This unconventional art installation was commissioned by the wealthy and quirky Stanley Marsh III. In the desert sands, ten Cadillacs are buried at a slant, and over the years, they have been covered in layers of vibrant spray-painted graffiti by visitors.
3. Santa Monica Pier Santa Monica, California

The iconic Santa Monica Pier sits just past the intersection of Ocean Avenue and Santa Monica Boulevard, marking the official end of Route 66. At the time of writing, the Ferris wheel had been auctioned off on Ebay and was in the process of being dismantled and transported to Oklahoma City!
2. Sitgreaves Pass (between Kingman and Oatman) Arizona

Route 66 meanders through the rugged Black Mountains en route to Oatman. Over the course of nine miles, the road ascends 1400 feet, and although it is treacherous with sharp, hairpin turns, the breathtaking views along the way are worth the challenge.
1. Blue Swallow Motel Tucumcari, New Mexico

Regarded as one of the oldest motels still operating along Route 66, the Blue Swallow is instantly recognizable thanks to its stunning and unique neon sign.
