Introduction to Route 66

Route 66 is often referred to as the most legendary road in America, made famous by Bobby Troup's classic song and brought closer to our hearts by Nat King Cole. Stretching from Chicago to Los Angeles, it's affectionately dubbed the "Mother Road," passing through many iconic cities and towns. Along the way, you can learn about the migration caused by the Dust Bowl in Amarillo, admire the neon-lit motels in Albuquerque, or visit Tulsa, where legends like Elvis Presley and Johnny Cash once graced the stage at Cain’s Ballroom — a venue that still hosts performances today.

As you journey between these famous stops, you'll encounter the rich tapestry of American culture, blending nostalgia, adventure, beauty, and history into an emotional road trip. But that’s just the beginning of what you can discover on Route 66. With a few detours, you’ll uncover quirky and unique American landmarks that have made this route famous today. Here are 15 one-of-a-kind spots you can't miss for an unforgettable experience on Route 66.

Cadillac Ranch

Perhaps one of the most iconic symbols of street art on Route 66 is Cadillac Ranch. Located just off Interstate 40, about 10 miles west of Amarillo, Texas, this installation features a row of 10 classic Cadillacs buried nose-first into the ground. This isn't a museum or an official attraction; you'll need to park along the road, walk through a gate, and trek across a dirt field to reach these colorful cars. Created in 1974, visitors are encouraged to bring spray paint and add their own artistic touch to this evolving masterpiece. The site is free and open 24/7, though there are no facilities for visitors. Address: 13651 I-40 Frontage Road, Amarillo, TX 79124.

Painted Desert

While Route 66 is often associated with vintage charm and nostalgia from the 1950s, there’s also a wealth of natural beauty to explore, particularly in the West. One of the most stunning stretches is in northern Arizona, where Route 66 winds through the Petrified Forest National Park. You can drive the park's 28-mile road, discover scenic viewpoints, short walking trails, and remnants of the original highway with its ancient telephone poles stretching across the desert. Address: 1 Park Rd, Petrified Forest National Park, AZ 86028.

Ed Galloway's Totem Pole Park

A must-visit artistic stop along Route 66 is Ed Galloway's Totem Pole Park, located near Foyil, Oklahoma. Built from 1937 to 1948 by self-taught artist Ed Galloway, the park's highlight is a towering 27-foot totem pole surrounded by smaller towers and carved animals, along with a quirky museum known as the "Fiddle House." The park is free and open from morning till night, while the museum usually operates from March to December. Unlike many roadside attractions, this place is not just a photo op but a unique artistic space created by one individual.

Shea's Gas Station Museum

Next on your journey is Shea's Gas Station Museum in Springfield, Illinois — or what's left of it. Once a Texaco station (later Marathon) that operated from 1946 to 1982, it was transformed into a museum showcasing vintage gas pumps, signs, and roadside memorabilia in the 1980s. However, the museum has been mostly closed since the owner's passing in 2013, with many items auctioned off. Today, it serves as a photo stop, though the current owner occasionally tries to open it when possible. You can reach out via Facebook for current opening hours.

Texas Tornado Tower

One of the quirkiest roadside illusions on Route 66 is the Texas Tornado Tower — a water tower located near Interstate 40 in the small town of Groom, Texas. From a distance, it appears to be on the verge of collapse, but fear not: it was intentionally built that way. Originally a water tank, it was purchased and crafted into a leaning tower to attract drivers to a nearby rest stop. Today, the rest stop is no longer operational, but the tower remains a classic photo opportunity on Route 66.

The World's Largest Rocking Chair

One of the most bizarre roadside attractions on Route 66 is the world's largest rocking chair, standing at 42 feet tall, located in Fanning, Missouri. It's easily visible from afar and can't be missed, just as intended. It serves no real purpose other than to entice drivers to stop for a photo op, and you can grab some snacks nearby. The site is free and open year-round, featuring a small shop selling homemade treats and a nearby rest area if you want to linger a bit longer. This is a perfect example of the quirky charm of Route 66: creating something big and silly to draw in travelers.

The World's Largest Ketchup Bottle

If a 42-foot rocking chair isn't enough for you, head over to the world's largest ketchup bottle. This 170-foot tall water tower shaped like a ketchup bottle is located in Collinsville, Illinois. Built in 1949 for the nearby Brooks ketchup factory, it was designed to promote the product made inside — and has become a quirky architectural piece of the past century. There’s a small parking lot nearby for visitors to stop and take photos, and it’s open 24/7 for anyone wanting to visit.

Roy's Motel and Cafe

In the Mojave Desert, essentially in the middle of nowhere, you'll find Roy's Motel and Cafe. Established in 1938 along Route 66, it quickly expanded into a complex that included a gas station, diner, and motel, catering to travelers passing through the seemingly barren desert. Architecturally, Roy's is one of the best remaining examples of Googie style, a mid-20th-century design influenced by the space age and aimed at grabbing the attention of drivers on the highway. Currently, the motel and cafe are being restored, while the gas station and store remain open.

Wigwam Motel

One of the most recognizable accommodations on Route 66 is the Wigwam Motel in Holbrook, Arizona, where guests can sleep in concrete "wigwams" (though they actually resemble teepees). Built in 1950, this motel is among the must-see spots when traveling along Route 66.

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Introduction to Route 66