Historic Road Trip Wonders

Some roads double as time machines, guiding you past monuments that have stood for generations. Every mile brings you face-to-face with America’s strangest and most lovable roadside oddities. They were carved long before GPS was even a thought. What remains today is nostalgia and a living scrapbook of the nation's unforgettable detours. Let’s uncover the 20 oldest American roadside attractions worth a stop.

Carol M. Highsmith on Wikimedia

1. Lucy The Elephant – Margate, New Jersey

Six stories tall and shaped like an elephant, Lucy was built to promote real estate back in 1881. Now, she’s a National Historic Landmark offering panoramic views and a peek into a time when marketing meant building a 90-ton pachyderm. Don’t be in New Jersey and not get a glimpse.

Navya Sriramaneni on Wikimedia

2. Cabazon Dinosaurs – Cabazon, California

Towering over I-10 since the 1960s, these massive concrete dinos started as a restaurant gimmick. They’ve since become stars in movies and memes. Visitors still climb inside Mr. Rex for a view of retro roadside flair and a desert view.

Jllm06 on Wikimedia

3. The Blue Whale – Catoosa, Oklahoma

The Blue Whale has been resting on Route 66 since 1972. It was originally a family swimming hole. Over the years, it has been painted and patched. Today, the whale is a selfie magnet and a nod to old-school American kitsch that refuses to sink.

Ben Turover (Turover at en.wikipedia) on Wikimedia

4. The World's Largest Ball Of Twine – Cawker City, Kansas

Started in 1953, this ever-growing ball of twine blends roadside oddity with homespun tradition. Travelers keep adding strands, turning it into a living sculpture. It began as a personal project, but now, it symbolizes persistence and the simple joy of slow, collective creation.

Visiting the World’s Largest Ball of Twine - Cawker City Kansas by Mike Less - Farmhand Mike

5. The Coral Castle – Homestead, Florida

After being left by his fiancée a day before their wedding, Edward Leedskalnin spent decades building a limestone monument to lost love—by himself. He shaped and stacked over 1,000 tons of coral rock using no machinery. The heartbreak is carved into every stone.

Ebyabe on Wikimedia

6. The Shoe House – Hallam, Pennsylvania

The Shoe House was constructed in 1948 by a shoe salesman who embraced creativity. This giant boot-shaped home straddles fantasy and advertising. Now a museum, it captures mid-century Americana where charm met commerce.

PLBthetoonist on Wikimedia

7. South Of The Border – Dillon, South Carolina

Since the 1950s, this neon-soaked I-95 fixture has amused and polarized passersby. Packed with giant sombreros, fireworks, and fiberglass animals, it’s a chaotic time capsule. Love it or cringe at it, you’ll remember this one, and that’s exactly what a roadside spectacle aims to do.

Plantsmushrooms on Wikimedia

8. Wall Drug Store – Wall, South Dakota

In 1931, a promise of free ice water transformed this humble drugstore into a sprawling 76,000-square-foot spectacle. Today, it’s a whirlwind of taxidermy and five-cent coffee. Every wall and corridor competes for your attention. What began as a roadside refreshment now defines maximalist Americana.

Runner1928 on Wikimedia

9. The Wigwam Motel – Holbrook, Arizona

Opened in 1950 along historic Route 66, this motel features 15 concrete wigwams arranged in a semicircle, each equipped with basic amenities. It’s one of only three surviving Wigwam Villages in the U.S. and is listed on the National Register of Historic Places for its roadside architectural significance.

Marine 69-71 on Wikimedia

10. The Mystery Spot – Santa Cruz, California

The Mystery Spot has baffled visitors since 1940. Within its 150-foot zone, objects seem to defy gravity and orientation. The tilted house creates optical illusions that make people appear to lean or change height. It has been drawing curious crowds and ongoing debate ever since.

Tshrinivasan on Wikimedia

11. The World's Largest Catsup Bottle – Collinsville, Illinois

This roadside weirdness turned into an architectural legend. Completed in 1949, the 170-foot-tall water tower is shaped like a catsup bottle. It was once an actual advertisement. Though retired from utility, it still stands proudly beside Route 159. Drivers slow down just to gawk.

Inehmo on Wikimedia

12. The Giant Paul Bunyan Statue – Bemidji, Minnesota

Made in 1937 as part of a winter carnival promotion, this 18-foot statue of Paul Bunyan stands beside his 10-foot blue ox, Babe. Recognized as one of America’s first and most famous roadside giants, it’s listed on the National Register of Historic Places.

Another Amazing Roadside Attraction! Paul Bunyan and His Blue Ox, Babe — Video Dispatch by Listening to America with Clay Jenkinson

13. Dinosaur Park – Rapid City, South Dakota

The concrete dinos have watched over the Black Hills since 1936. Designed during the Depression to lure tourists, they’re delightfully outdated. But that’s the appeal—angular and entirely unapologetic. It’s a Jurassic stroll through America’s pre-digital charm.

Minnesota Jones at en.wikipedia on Wikimedia

14. The Madonna Inn – San Luis Obispo, California

This 1958 hotel leans all the way into eccentricity. Each room has its own wild theme, ranging from caveman suites to floral fever dreams. Covered in pink, gold, glitter, and a pseudo-Swiss Alps exterior, it’s a romantic fever dream you escape to or from.

Cory Doctorow from Beautiful Downtown Burbank, USA on Wikimedia

15. The Big Duck – Flanders, New York

Martin Maurer, the duck farmer who built it, did it in the most literal way possible. It's a 1931 architectural quirk that doubles as a sales pitch. The giant duck once sold poultry and now sells memories. Its glowing eyes and odd proportions make it unforgettable.

Photograph by Mike Peel (www.mikepeel.net). on Wikimedia

16. The Giant Coffee Pot – Bedford, Pennsylvania

Constructed in 1927 beside a gas station on the Lincoln Highway, an 18-foot-tall structure was designed to catch the eyes of passing motorists. It served as a lunch stand selling coffee and snacks. It has been restored and relocated near the Bedford County Fairgrounds.

Jeff Kubina from Columbia, Maryland on Wikimedia

17. Clark’s Trading Post – Lincoln, New Hampshire

In the 1920s, it sold trinkets. Today, it hosts steam trains and bear shows in the White Mountains. Still run by the same family, the place blends wilderness kitsch with small-town aesthetics. Nothing here feels corporate, and that’s exactly the point.

Kenneth C. Zirkel on Wikimedia

18. The Leaning Tower of Niles – Niles, Illinois

Completed in 1934 as a decorative water tower, this half-size Pisa replica turned heads long before travel influencers existed. It was built for a YMCA complex and accidentally became a roadside icon—quirky and still leaning proudly in suburban Illinois.

Ken Lund from Reno, Nevada, USA on Wikimedia

19. The World’s Largest Chest Of Drawers – High Point, North Carolina

The 38-foot dresser promoted High Point’s booming furniture trade. Two dangling socks reference the local hosiery industry. The original chest of drawers, built in 1936, was remodeled in 1996 into the Queen Anne-style structure that exists today, designed by Sid Lenger.

Cmalaspina on Wikimedia

20. The Petrified Wood Gas Station – Lamar, Colorado

This tiny gas station was built using actual petrified wood. It's a geological masterpiece on the plains. Though no longer operational, it’s preserved as a local landmark and listed on the Colorado State Register of Historic Properties.

Carol M. Highsmith on Wikimedia