1. Cadillac Ranch – Amarillo, Texas
Driving through Texas? You can’t miss this quirky, larger-than-life art installation right off Route 66. Cadillac Ranch is a row of vintage Cadillacs buried nose-first in the dirt, all covered in colorful graffiti. Visitors are encouraged to grab a can of spray paint and leave their mark, so the look of these cars is always changing. Just make sure to bring an extra can for the next visitor!
2. Wall Drug – Wall, South Dakota
Wall Drug is part travel stop, part museum, and part cowboy-themed amusement park. Originally a simple drugstore offering free ice water to travelers, it’s grown into a massive complex of shops, eateries, and kitschy photo-ops. Plus, it’s one of the few places you can get a fresh donut, a buffalo burger, and a cup of 5-cent coffee in one spot.
3. The World’s Largest Ball of Twine – Cawker City, Kansas
There are several giant balls of twine across America, but the one in Cawker City has a special status—it’s the largest one that’s still actively growing. This huge ball of twine, started by a local farmer in 1953, gets a little bit bigger every August during the city’s Twine-a-thon, when visitors can add their own twine to the ball.
4. The Fremont Troll – Seattle, Washington
Seattle’s Fremont neighborhood is home to a massive troll sculpture under the Aurora Bridge. The troll, gripping an actual VW Beetle in one hand, has become a beloved piece of local art. Visitors love to climb on it for photos, making it a must-see for anyone exploring Seattle’s quirkiest spots.
5. Mystery Spot – Santa Cruz, California
The Mystery Spot is a strange little area in the redwoods where the rules of gravity seem to go haywire. Rooms feel tilted, objects roll uphill, and people can lean at impossible angles. The owners say it’s all about “gravitational anomalies,” but some think it’s just a cool optical illusion. Either way, it’s a fun and brain-bending experience.
6. The Wigwam Motel – Holbrook, Arizona
Spend the night in a real-life tepee at the Wigwam Motel! Built in the 1950s, this retro motel features individual “wigwams” that are actually cozy little rooms, perfect for Route 66 travelers looking for a one-of-a-kind stay. It’s quirky, nostalgic, and close to other Route 66 landmarks like the Petrified Forest.
7. The Enchanted Highway – Regent, North Dakota
This 32-mile stretch of road is home to some of the largest scrap metal sculptures you’ll ever see. From towering grasshoppers to giant pheasants, each sculpture is a creative and slightly surreal sight. Created by a local artist to attract tourists, the Enchanted Highway is an open-air gallery of Americana.
8. Lucy the Elephant – Margate, New Jersey
Lucy is a six-story-tall elephant-shaped building that’s over a century old. Originally built as a gimmick to sell real estate, Lucy has survived hurricanes and even plans for demolition. Today, you can tour the inside, where you’ll find museum exhibits and one of the quirkiest views of the New Jersey coastline.
9. Dinosaur Land – White Post, Virginia
Dinosaur Land has been delighting families since the 1960s with its 50+ life-sized dinosaur statues, including a massive T. rex and a brontosaurus. It’s delightfully low-tech, and there’s a vintage charm to it that makes you feel like you’re stepping back in time. Plus, the gift shop is packed with classic dino-themed souvenirs.
10. Carhenge – Alliance, Nebraska
Imagine Stonehenge, but made from old cars painted gray and arranged in a field. Carhenge is just that—a quirky roadside attraction built by a local artist as a tribute to his father. This car-based replica of the ancient monument is free to visit and even features some other fun car sculptures around the site.
11. Salvation Mountain – Niland, California
In the Southern California desert stands Salvation Mountain, a massive, colorful mountain of adobe and paint created by artist Leonard Knight. The mountain is covered in bright artwork and messages of love, hope, and faith. It’s an inspiring place for those looking to see something a little different off the beaten path.
12. The World’s Largest Rocking Chair – Casey, Illinois
Casey, Illinois, has a thing for “world’s largest” items, but its 56-foot-tall rocking chair is one of the most impressive. Made from wood and metal, the chair is certified by Guinness World Records and sits proudly along Main Street. Visitors can climb up to take a photo, although you’ll need a wide-angle lens to get it all in.
13. The Big Texan Steak Ranch – Amarillo, Texas
Famous for its 72-ounce steak challenge (eat it in under an hour, and it’s free), the Big Texan is a Texas-sized restaurant and motel along Route 66. The atmosphere is as big as the steaks, with a Wild West vibe, animal heads on the walls, and kitschy cowboy decor. Even if you’re not tackling the steak challenge, it’s a fun place to grab a hearty meal.
