12 Legendary Route 66 Attractions You Need to See Before You Die

Blue Swallow Motel

Like rivers, wind and the setting sun, roads are ripe with metaphor. They help us understand the twists and turns of life’s long journey and teach us to appreciate all those unexpected detours. But nowhere does the road-as-life metaphor offer more intrigue than the story of Route 66.
During the 1940s and '50s, Route 66 was known as “The Main Street of America.” The glittery new blacktop stretched more than 2,000 miles over eight states from Chicago to Los Angeles, winding through small towns, past hundreds of cafés, motels, gas stations and tourist attractions along the way. It was a journey from the Rust Belt to the Sun Belt that drew throngs of travelers eager to see the sights of the open road and the open country.

Beginning in the late 1950s, though, Route 66 was slowly bypassed section-by-section as construction of high-speed interstate highways drew travelers away. So far away, in fact, that in 1984 the road was decommissioned and removed from the U.S. Highway System altogether. But the story doesn’t end there. Not long after it was decommissioned, the all-but-forgotten two-lane road earned legendary status and a new moniker — Historic Route 66.
Today the two-week journey from end to end still retains its popularity with adventure-seekers and travelers longing for a forgotten America. What’s more, the roadsides of Route 66 are still sprinkled with some legendary attractions. Sure, the shine wore off years ago, but the worthy traveler may discover the old road still sparkles in places. Here are just a few of those places.

Illinois-Missouri Border
Built in 1929 and spanning one of the most scenic sections of the Mississippi River, the Chain of Rocks Bridge links St. Louis, Missouri, and Madison, Illinois, with a famous 22-degree bend in the middle and two notable water intake towers nearby. This mile-long pedestrian bridge also offers visitors an opportunity to cross this mighty river on foot or bicycle.

Stanton, Missouri
Missouri is known as the cave state, so it’s no surprise that one of the state’s best Route 66 stops is the impressive Meramec Caverns. Established as a tourist attraction in 1930, the caverns offer tours along with camping, canoe trips and gold panning nearby. Just as popular with travelers are the many roadside barns painted to promote the caverns.

Clinton, Oklahoma
Route 66 is so much more than its roadside attractions. This stretch of blacktop is saturated with decades of American history from the Dust Bowl to the Big Band Era and beyond. And while each state has its own unique museum, Oklahoma’s fun and informative walk-through gallery is one of the finest.

Catoosa, Oklahoma
In 1972, Hugh Davis built one of Route 66’s most recognizable attractions as an anniversary gift to his wife, Zelta. For decades after, the Blue Whale remained a beloved summertime hotspot for picnicking, swimming and fishing. Today this icon remains lovingly restored and maintained by Catoosa locals and offers a classic photo opportunity for travelers.

Amarillo, Texas
Pair up a Texas billionaire with some art hippies from San Francisco, and the result is big, colorful and timeless. Legend has it, these 10 half-buried Cadillacs match the angle of the Great Pyramid of Giza; however, unlike the pyramid, visitors here are encouraged to supply their own artistic contribution using spray paint.

Texas-New Mexico Border
By 1920, the small town of Glenrio thrived with grocery stores, cafés, service stations, hotels and a hardware store that sustained Route 66 travelers through the prosperous '40s and '50s. Today it stands as one of Route 66’s best ghost towns, home to architectural remnants and a still-intact main street reminiscent of the road’s bygone boom days.

Santa Rosa, New Mexico
Halfway between Amarillo and Albuquerque, a deep pool of crystalline water suddenly appears in the arid desert. Connected to six other sister lakes by a vast underground network of water, Blue Hole is a natural wonder offering 100 feet of underwater visibility and a constant 62-degree temperature, perfect for a Route 66 swim break.

Tucumcari, New Mexico
Because the town has maintained its days-of-old charm, a stopover in Tucumcari offers 21st century Route 66 travelers one of the best opportunities to step back in time. And a night at the family-owned Blue Swallow — with a historic courtyard, restored rooms, attached garages and brilliant neon lights — is an opportunity to linger there a while.

Northern Arizona
Route 66’s most impactful attraction is 50,000 years old and dubbed the world’s best-preserved meteorite impact site. At nearly a mile across and more than 550 feet deep, Meteor Crater offers three breathtaking lookout points, tons of interactive displays and exhibits, and a guided rim trail tour around the crater.

Arizona and California
Of the original seven Wigwam Village Motels popular during the 1930s, only three still remain today, and two call Route 66 home. Wigwam Village No. 6 in Holbrook, Arizona, and Wigwam Village No. 7 in Rialto, California, each offer individual rooms shaped like teepees and equipped with modern comforts. Additionally, Arizona’s village includes a classic car display.

Oro Grande, California
Elmer Long, beneficiary of his father’s extensive bottle collection, has created a quirky, colorful roadside forest of more than 200 bottle trees spread across 2 acres of California desert west of Barstow. While the sun and wind bring the forest to life, the most unique installation might be the story-telling curator himself.

Los Angeles, California
Because most travelers of the 1930s and '40s were heading west along Route 66, the Santa Monica Pier often marked the end of a long cross-country journey. But with such a spirited variety of entertainment, food and shopping, it’s the most appropriate grand finale to an equally grand adventure.