Centennial Cruising: Six Essential Stops to Celebrate 100 Years of Route 66

SPRINGFIELD, Missouri — Route 66 remains the ultimate symbol of the classic American cross-country road trip. Immortalized by Jack Kerouac in On the Road with the phrase, "Nothing behind me, everything ahead of me," the historic highway is celebrating its landmark 100th anniversary.

Born out of an early 1920s partnership between federal planners and local entrepreneurs, U.S. Highway No. 66 grew from a patchwork of local trails into a 2,400-mile artery linking Chicago to Los Angeles. Over the decades, it transformed from a Dust Bowl escape route into a pop-culture phenomenon, celebrated by John Steinbeck, Woody Guthrie, and Bobby Troup's classic anthem, "(Get Your Kicks On) Route 66."

As global travelers prepare to celebrate the road's centennial, here are six essential stops that capture the enduring spirit of the Mother Road.

1. St. Louis, Missouri

Route 66 makes its modest debut among the skyscrapers of downtown Chicago before cutting across the Illinois prairie, largely replaced today by Interstate 55. However, the highway makes a truly dramatic entry into Missouri as it leaps across the Mississippi River.

* The Old Chain of Rocks Bridge: This historic one-mile span is no longer open to motor vehicles, but it has been beautifully preserved for pedestrians and cyclists, complete with vintage Route 66 trail markers.

* Downtown Architecture: The highway followed several alignments through the city, offering travelers excellent views of the French Renaissance-style City Hall, the Old Courthouse, and the Gateway Arch.

* Ted Drewes Frozen Custard: Operating on the edge of the city since 1941, this legendary roadside stand is world-renowned for its ultra-thick "concrete" vanilla custard shakes.

2. Springfield, Missouri

Springfield holds a special place in highway lore as the official birthplace of Route 66. It was here in 1926 that local businessman John T. Woodruff championed the designation of the number "66," choosing it purely because he believed it possessed a memorable, rhythmic ring for marketing purposes.

To celebrate the centennial, the local History Museum on the Square is launching a comprehensive "Miles of Memories" exhibition. The city will also host the massive Birthplace of Route 66 Festival on August 7–8, featuring live music, food trucks, and a classic car show centered around Park Central Square. Visitors can also step back in time by booking rooms at two beautifully restored 1930s properties: the Rockwood Motor Court and the Route 66 Rail Haven motel.

3. Tulsa, Oklahoma

If Springfield is the birthplace, Tulsa is home to the "Father of Route 66"—businessman Cyrus Avery, who worked tirelessly to pave the road and promote early automobile tourism. Tulsa fully embraces its asphalt heritage with beautifully preserved commercial hubs.

"Route 66 came along when the idea of a road trip was just getting started," notes Sean FitzGibbons, executive director of the History Museum on the Square. "It encapsulated so much of 20th-century Americana and over time it just kind of gained this mythical resonance within the zeitgeist of the world."

The city's historic Meadow Gold District features a massive collection of restored, glowing neon signs alongside whimsical roadside shops like Buck Atom’s Cosmic Curios, guarded by a 21-foot-tall "Space Cowboy" Muffler Man statue. On May 30, Tulsa hopes to secure a Guinness World Record for the largest classic car parade during the Route 66 Capital Cruise, sending hundreds of vintage vehicles down 11th Street past the newly opened Mother Road Market food hall.

4. Albuquerque, New Mexico

After traversing the Texas Panhandle—home to the famous Cadillac Ranch art installation near Amarillo—road-trippers enter New Mexico, where Albuquerque offers an unmatched treasure trove of historic "Pueblo Deco" architecture along Central Avenue.

Buildings like the 1927 KiMo Theater and the 1937 El Vado Motel showcase how Southwestern Native American culture directly influenced mid-century roadside styling. Rather than tearing down historical infrastructure, local business owners have cleverly repurposed old filling stations. The 1946 Andy Johnston Service Station now operates as Fan Tang Asian fusion restaurant, while another vintage depot has morphed into the highly popular, neon-drenched 66 Diner.

5. Winslow, Arizona

The small desert town of Winslow was nearly destroyed economically when Interstate 40 bypassed the original downtown alignment in the late 1970s. However, a singular line in the Eagles' 1972 hit song "Take It Easy" sparked a multi-decade tourism renaissance.

Today, the intersection of Kinsley Avenue and Old Highway 66 features Standin' on the Corner Park, complete with a bronze statue of singer Glenn Frey, a flatbed Ford truck, and a massive two-story mural. Travelers looking for upscale vintage luxury can stay at the historic La Posada Hotel, an architectural masterpiece designed by Mary Colter that opened in 1930 to serve wealthy motorists. Winslow's centennial schedule includes a Native American Powwow, lowrider showcases, and an expansive summer concert series.

6. Amboy, California

Deep within the striking landscape of the Mojave Desert lies Amboy, an authentic Route 66 ghost town that has refused to die. The town's crown jewel is Roy’s Motel & Café, an architectural masterpiece of sharp, mid-century modern "Googie" design.

Though bypassed by the interstate in 1972 and left abandoned for decades, the entire town was purchased by preservationists who have meticulously brought it back to life. Roy's famous 50-foot-tall neon sign was fully restored and illuminates the desert sky every evening at sunset. While the interior diner is still undergoing renovations, the property functions as a full-service, retro fueling station and convenience store for travelers completing the final leg of the journey toward the Santa Monica Pier, where the historic highway finally terminates at the Pacific Ocean.

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