A bustling pier with crowds of people, a Ferris wheel, and amusement rides, overlooking a sunny beachfront.

13 Vintage Stops on Route 66 That’ll Transport You Back in Time

Route 66, one of the first highways in the US, stretches from Illinois to California. If you’re gearing up for an unforgettable road trip along this iconic route, you have to discover the must-visit spots, including quirky attractions, charming diners, and stunning national parks.

I’ve compiled a list of the top stops along Route 66 that will add excitement and lasting memories to your journey.

1. Cozy Dog Drive-In – Springfield, Illinois

Diner
Photo Credit: Deposit Photos.

One of the places you absolutely shouldn’t miss for breakfast, lunch, or dinner is the Cozy Dog Drive-In. While they serve all three meals, I recommend checking it out during lunch. 

This old-school diner is known for serving delicious corn dogs, hot dogs, and burgers. It also sells loads of Route 66 memorabilia, perfect for commemorating your time at the diner and on your legendary road trip. 

2. Blue Whale – Catoosa, Oklahoma

A large blue whale-shaped playground structure by a pond, with a slide coming out of the mouth and a viewing scope on top.
Photo Credit: Deposit Photos.

The Blue Whale of Catoosa is a must-see quirky spot along Route 66. As the name suggests, it’s a massive structure made to look like a blue whale! Built by Hugh S. Davis in 1972 for his grandkids to play near the pond, it quickly became a hit with travelers. 

Today, it’s a popular spot for photo ops and picnics. Visitors also appreciate the seasonal restroom, making it a convenient and enjoyable stop.

3. Pops – Arcadia, Oklahoma

A brightly lit red and white spiraling sculpture resembling a soda bottle with a straw, in front of a building at twilight.
Photo Credit: Deposit Photos.

Pops is a one-stop shop on Route 66, with a restaurant, gas station, and convenience store. It’s famous for its various bottled sodas and features a huge 66-foot-tall soda bottle with LED lights. 

It’s a fun and convenient stop that everyone, kids and adults alike, will enjoy. And don’t forget to grab some memorabilia like t-shirts, hats, or stickers to remember your visit!

4. Oklahoma Route 66 Museum – Clinton, Oklahoma


A museum exhibit depicting a covered wagon with figures dressed in historical clothing, reminiscent of the American pioneer era, set against a backdrop of a desert sunset.
Photo Credit: Deposit Photos.

If you love history and Route 66, don’t overlook the Oklahoma Route 66 Museum. Here, you’ll find captivating photos and stories about this famous highway, along with myths and stories. 

Dive into the past and experience the Dust Bowl era, learning about the challenges and migrations to California along this historic route. It’s a fascinating journey through time for anyone interested in Route 66’s history!

5. Gateway Arch – St. Louis, Missouri

Gateway Arch National Park 1

When you think of St. Louis, Missouri, the towering 630-foot-tall monument arch likely comes to mind. Whether you’re driving through or strolling around the city, you’re bound to catch a glimpse of this iconic structure. But did you know you can explore inside it?

The arch project began in 1935 during President Franklin D. Roosevelt’s era but wasn’t completed until 1965. It stands as a symbol of national identity and mid-century modern design, celebrating the influential figures of the region like Thomas Jefferson, Lewis & Clark, Dred, and Harriet Scott, among others. Today, visitors can ride a tram to the top, tour the museum, or even ride a riverboat nearby.

6. Meramec Caverns – Stanton, Missouri

Tourists, including children and adults, are exploring the interior of a cavern with stalactites and rugged rock formations, following a path with a handrail.
Photo Credit: Shutterstock.

Meramec Caverns, located in Missouri’s Ozarks, is a series of caves with unique limestone formations. It’s a fascinating and slightly spooky experience you should see for yourself. These caves are as tall as a 7-story building, making them very impressive. 

Besides exploring the caves, there are many fun activities like ziplining, riverboat rides, and a wax museum. It’s perfect for families and kids under five can explore the caverns for free!

7. Cars On The Route- Galena, Kansas

Three vintage trucks with anthropomorphic features displayed outside a classic service station under a blue sky with fluffy clouds.
Photo Credit: Deposit Photos.

If you haven’t already watched the classic Pixar film “Cars,” it’s a must-see before embarking on your iconic Route 66 road trip. As you venture into Kansas, take the chance to visit Cars On The Route in Galena.

Legend has it that the director and animator of “Cars” found inspiration for the character Tow Mater when they visited this Kan-O-Tex Service Station and spotted a rusty tow truck. Today, you can see a few old cars resembling famous movie characters. It’s a fantastic photo opportunity, and kids will love it. It’s like stepping into the funky world of the movie.

8. Tower Station and U Drop Inn Cafe – Shamrock, Texas

A historic Conoco gas station with art deco architecture and vintage gas pumps under a clear blue sky.
Photo Credit: Deposit Photos.

The Tower Station and U Drop Inn Cafe were built in 1936. This architectural gem is one of the most distinctive buildings along Route 66 and was originally used as a bustling stop for travelers to refuel, dine, and shop at a retail store (which later became extra seating for the cafe).

Today, this quirky establishment serves as a Visitor Center and Chamber of Commerce. It’s a perfect spot for snapping photos, exploring a charming gift shop, and even recharging at the electric vehicle charging station.

9. Cadillac Ranch – Amarillo, Texas

Cadillac Ranch

Cadillac Ranch in Amarillo is a fun stop along Route 66. Despite its name suggesting a collection of Cadillacs on a ranch, it’s far more interesting. The site features ten vibrant, painted Cadillacs buried nose-deep in the ground, creating a series of cars sticking up in the air. 

This artsy display was created in 1974 by the Ant Farm art group and continues to draw visitors as a famous attraction along the route. It’s a fantastic spot for art enthusiasts and anyone looking to take funky photos.

10. Blue Hole – Santa Rosa, New Mexico

A woman in swimwear gracefully free diving underwater, with light refracting on the surface above her.
Photo Credit: Deposit Photos.

If you want to get out of the car, stretch your legs, and swim, this is the spot for you. The Blue Hole of Santa Rosa is a swimming and scuba diving favorite. It is unique because it always has plenty of water despite New Mexico’s dry weather. 

Its deep blue color and clear visibility make it perfect for scuba diving. With a steady temperature of 62 degrees, it’s a great addition to your road trip for some swimming and excitement.

12. Petrified Forest National Park, Arizona

A person stands at the edge of a desert overlook, gazing out over the striated, colorful formations of a vast canyon landscape under a clear sky.
Photo Credit: Deposit Photos.

Petrified Forest National Park in northeastern Arizona boasts numerous fascinating attractions. It’s an ideal stop on your Route 66 road trip because it offers a bit of everything and provides a perfect opportunity to stretch your legs and enjoy some exercise.

The park is renowned for its fantastic hiking, walking, and backpacking trails. In addition to these excursions, you can appreciate petroglyphs at Newspaper Rock, where over 650 rock carvings created by the ancient Puebloan people are displayed. You can also discover the history of Puerco Pueblo, once a thriving home for the Pueblo people. This park is an excellent place for outdoor enthusiasts and history buffs alike.

13. Elmer’s Bottle Tree Ranch – Oro Grande, California 

Rows of metal trees adorned with colorful glass bottles lining a roadside in a desert environment, under a bright blue sky.
Photo Credit: Deposit Photos.

Elmer’s Bottle Tree Ranch, created by Elmer Long, showcases countless tree-like structures made from different materials, with limbs made of colorful glass bottles. It’s a unique and artsy site unlike anything you’ve seen before. 

This fascinating attraction reflects one man’s dedication to art and presents something unique to appreciate. Today, it’s one of the most eccentric stops along Route 66, attracting numerous visitors who come to take photos and enjoy the different artwork throughout.

14. Santa Monica Pier, California 

Couples at Santa Monica Pier.
Photo Credit: Deposit Photos.

The Santa Monica Pier is a popular attraction and a great place to go for fishing, strolling, and enjoying the scenery. It also features a small amusement park. The Ferris wheel is a favorite, offering fantastic views from the top. 

You’ll also find various musicians and street artists performing on the pier. It’s a lively destination offering a bit of everything along the California coast.

Author: Abby Price

Title: Journalist

Expertise: Travel, Snow Skiing, Outdoors

Abby Price is a journalist, travel and ski writer, and the founder of the digital publications Summit Skier and Trekking Price’s. She is an expert on skiing, snowboarding, ski resorts, and United States travel. 

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