America's Most Iconic Highway Is A Must-Do Road Trip In 2026 - Here's Why

As the song goes, "It winds from Chicago to L.A., more than 2,000 miles all the way." Since 1926, Route 66 has been delivering neon nostalgia and kitschy Americana, and it has inspired countless road trips and one killer song. Well, the nation's most iconic highway is celebrating its centennial. So give your jalopy a tune-up and put together a mix-tape or two, because 2026's must-do road trip demands you get your kicks on Route 66.

Necessity inspired Route 66's creation, as Oklahoma businessman Cyrus Avery sought a way to bring prosperity to his town by connecting the West and the Midwest. With other business barons, Avery successfully lobbied for the creation of a civil engineering feat that skipped and hopped on a diagonal course between Chicago and Los Angeles, connecting smaller locales along the way. The highway became a favorite among truckers, who preferred its amble across the prairies and gentler climates, while the boom in personal automobiles drove the creation of a cottage road stop industry along the route.

The resulting hodgepodge of landmarks and quirky attractions earned Route 66 a cultish status in America's cultural consciousness. John Steinbeck gave the highway its nickname, "the Mother Road," in his classic novel, The Grapes of Wrath. It's also honored in a now-classic song written by Bobby Troup and covered by the likes of the Rolling Stones and John Mayer. It eventually shared the title of "The Main Street of America" with Route 40. Disuse and the construction of newer superhighways eventually led to Route 66's decommissioning. Yet its epic history will be recognized in 2026 with Civil Engineering Landmark status, which puts it on level with icons like the Hoover Dam and Golden Gate Bridge. 

The centennial celebration will include the expected grab bag of memorial signs, renovation projects, and artistic endeavors. The exact details and bold-faced names at various events are still in the works. Still, each state along the route will host its own celebratory gatherings. Events will begin at the centennial's official kickoff on April 30 in Springfield, Missouri — the "Queen City of the Ozarks," brimming with big flavors and quirky vibes. The event will include a concert headlined by A-listers, as organizers promise more info as the date approaches. 

The heart and soul of the bacchanal, however, will be in Cyrus Avery's hometown of Tulsa, Oklahoma — the wildly underrated Southern music city will be home to "the Mother of all Road Fests" on June 27 and 28. Classic cars and interactive exhibits will fill Expo Square. Vintage RVs and family-friendly activities will keep visitors busy, while vendors will help provide at least a new keychain for your car keys. The Sooner State has 16 events scheduled for the centennial celebration as of writing, giving visitors plenty to enjoy. 

Route 66 is a highway, after all, so a car-centric event only makes sense. The Route 66 Road Rally will explore the 100-mile stretch of Route 66 between Edmond and Sapulpa. The 11-city trek will include selfie checkpoints and a $1,000 prize, all while exploring some of the smaller communities that benefited from the highway's creation. The centennial celebrations will also be a car lover's paradise.

Visitors and participants should turn the celebration into a road trip. Shadowing The Great Race is your best bet. The nine-day roving vintage car rally will cruise the entire route, from Illinois to California. Cars built between 1911 and 1974 will stop in cities along the way to promote the 100th anniversary. The race is already full of participants, but nobody's stopping you from following in their tire tracks. 

Those tight on time can stop by any of the car shows that'll fill the 2026 calendar with classic cars and custom builds. Arizona's festivities include a laundry list of car shows, including two in the late spring. The Gunslinger Car Show will take place on May 31 in Holbrook, a quirky city in Arizona's painted desert. It will be quickly followed on June 6 by the Williams Historic Route 66 Car Show, featuring over 500 automobiles from trucks to motorcycles, with a burger burn and parade to boot.

Celebrations will include a smattering of concerts in states along the route. New Mexico's Route 66 Summerfest on July 19 plans to make a full-blown music festival out of the centennial in Albuquerque. Local bands will perform across several stages, with food trucks helping make up for all the calories you'll burn off while dancing.

Route 66 didn't need to reach its 100th birthday to earn a celebration. The Route 66 Fun Run has commemorated the road since 1988, led by the Arizona Historic Route 66 Association. The group successfully lobbied the Grand Canyon State to revive Route 66 as a historic highway, and began celebrating its success with a 140-mile drive from Topock and Seligman, Arizona's gateway to the Grand Canyon. That tradition continues, and will take place from May 1 to 3. Be sure to throw a drive along Sitgreaves Pass into the mix; the winding, high-elevation section of Route 66 has panoramic views and historic sites.

The Route 66 celebrations will last throughout the year, giving visitors and fans some flexibility in when they can go. Be sure to put together a top-notch playlist for your drive. Whether you prefer Nat King Cole's original version, The Rolling Stones' hip-shaking take, or Chuck Berry's swaggering style, be sure "(Get Your Kicks on) Route 66" has a home somewhere on the list.