The highway’s upcoming centennial celebrations will spotlight iconic sites recalling the golden age of automobile travel
By Randy Mink
For a true slice of Americana, few journeys in the Midwest can rival a road trip that retraces the path of our nation’s most storied highway. Nicknamed the “Mother Road” in John Steinbeck’s classic 1939 novel, The Grapes of Wrath, U.S. Route 66 was the magic carpet to dreams in the mid-20th century. Symbolizing freedom and mobility, it attracted vacationers, adventurers, hippies and those searching for a better life.
Forming a linear community that spanned more than 2,400 miles from Illinois to California, the concrete corridor became enshrined in popular culture — in music, art, films and television shows as well as literature. Route 66 became known as the “Main Street of America.” Cozy motels, mom-and-pop cafes, filling stations, neon signs and roadside oddities were all part of its mystique.
Missouri and seven other states, in cooperation with the U.S. Route 66 Centennial Commission, will be working on special projects and activities to celebrate the road’s 100th anniversary in 2026. In the coming years, you’ll be hearing a lot about the commemorations planned and the many attractions that preserve the road’s history.
Springfield, Missouri, is considered the birthplace of Route 66. It was from a hotel there in 1926 that Missouri and Oklahoma highway executives sent federal officials a telegram proposing the new road be called U.S. Highway 66, a designation approved a few months later. John T. Woodruff, a Springfield attorney and businessman who promoted roads in the Ozarks and elsewhere, was elected as the first president of the National Route 66 Association in 1927.
Starting in the late 1950s, Route 66 was gradually replaced by high-speed interstates. While the pioneering pathway’s official decommissioning in 1985 marked the end of an era, the legacy of the fabled east-west artery lives on. Interstate 44 may have replaced Route 66 in Missouri, but hundreds of “Historic Byway” signs recognizing the original route can be found across the state.
Visit diners, natural wonders and roadside attractions in Springfield on Route 66
In Springfield, most reminders of Route 66’s glory days are clustered in the downtown area, mainly along College and East St. Louis streets, which have black-and-white “Missouri Route 66” shields painted on the pavement.
On Park Central Square, downtown’s hub, the History Museum on the Square is the ideal place for Route 66 fans to get their kicks. A 66-foot-long timeline and map traces the highway’s history, showing classic diners, motels, natural wonders and kitschy roadside attention-getters in the eight states through which it traveled.
Artifacts from Springfield include a Standard Red Crown gas pump, a Sunset Drive-In movie theater sign, an A&W Root Beer curbside ordering box, a jukebox, and a sign and menu from Red’s Giant Hamburg, considered America’s first restaurant with a drive-up window when it opened in 1947. (The name originally was meant to be Red’s Giant Hamburger, but the “er” was cut off at the bottom when Red Chaney realized the sign was too tall to fit under overhead power lines.) Museum visitors will see vintage postcards, a Steak ‘n Shake booth and a turquoise Chevrolet convertible from the 1950s.
The Route 66 Car Museum is home to a variety of classic cars
Car culture naturally is a big part of Route 66, and the Route 66 Car Museum, one mile west of the Square, captures the vibe with antique gas pumps, oil cans, signs and other automotive memorabilia, not to mention aisles of restored vehicles buffed to a shine. Treasures on display include a black 1957 Corvette, a red 1956 Ford Thunderbird and a 1929 Ford Model A. The museum gift shop sells all kinds of Route 66 souvenirs and has a selection of old license plates from Missouri and other states.
The 1950s-era College Street Cafe, an unassuming diner with auto-themed decor, shares a parking lot with the Route 66 Car Museum. Offering home-cooked fare, the menu features comfort foods like meatloaf with mashed potatoes, a pork tenderloin sandwich with fries and country-fried steak in cream gravy.
A block east of the Square contains the Gillioz Theatre, a movie/vaudeville house that debuted on Route 66 in 1926. After closing its doors in 1980, the grand old theater sat unused until a massive restoration was completed in 2006. The Spanish Colonial Revival gem is now a venue for music acts, comedians, plays and movies.
The Steak ’n Shake on East St. Louis Street has served its steakburgers, fries, chili and milkshakes to hungry travelers since 1962. Sporting the original signage, it is one of three Steak ’n Shakes still located on old Route 66, offering both car-side service and a dining room with red vinyl seats, neon signs and old photos.
The retro theme continues in Springfield with three vintage, Route 66-themed motels that offer modern amenities — Best Western Route 66 Rail Haven, Rockwood Motor Court, and Rest Haven Court.
History comes alive in Ash Grove at a 1930s gas station with original pumps
In Ash Grove, 25 miles west of Springfield, take a cruise down memory lane at Gary’s Gay Parita, a replica 1930 Sinclair gas station with original pumps and loads of Route 66 collectibles on display.
In the southwest corner of Missouri, the legend of Route 66 lives on in Joplin, whose name is mentioned in the lyrics of the famous song “(Get Your Kicks on) Route 66.” Route 66 Mural Park on Main Street features two large tile murals and a red mock 1964 Chevy Corvette, a popular photo stop.
Northeast of Springfield in Lebanon, the public library includes a free-admission Route 66 Museum complete with re-creations of a ’50s diner and gas station, along with an antique car and other memorabilia.
Cuba, another town that maintains its Route 66 heritage, is home to the Wagon Wheel Motel, a restored tourist court that has put up road trippers in its stone cabins since the 1930s. Its neon sign dates back to 1947. Visitors to Cuba, about 75 miles southwest of St. Louis, also seek out the 14 supersized outdoor murals that showcase the highway’s heyday and local history. For the best in comfort food, try Cuba’s Missouri Hick Bar-B-Q. Outside of town, don’t miss the Route 66 Rocker. Standing more than 42 feet tall next to Fanning Outpost General Store, the bright orange rocking chair is the world’s second-largest.
Meramec Caverns is one of the best caves in the country for groups to visit
Since the 1930s, motorists in Missouri have seen the name Meramec Caverns emblazoned on barns and billboards. An early fixture on Route 66, the quintessential show cave is located near Stanton, an hour or so outside of St. Louis via I-44. Delivering relief from the summer heat, the cave is a constant 60 degrees year-round. In a natural theater on the fourth level, tours conclude with a patriotic sound-and-light spectacle projected onto the Stage Curtains, a 70-foot-tall rock formation.
In Eureka, west of St Louis, I-44 exits take you to Route 66 State Park, situated along the Meramec River. One exit leads to the visitor center, a former 1935 roadhouse where museum exhibits tell the stories of Route 66 and Times Beach, a Route 66 community that occupied the riverfront from 1925 until the early 1980s. The gift shop has an extensive variety of Mother Road souvenirs, from games, puzzles and books to videos, T-shirts, metal signs, mugs and magnets.
In St. Louis, the largest city on Route 66 between Chicago and Los Angeles, Ted Drewes Frozen Custard has been a favorite stop since 1929. Its signature milkshake has earned the name “concrete” because it’s so thick you can turn it upside down without spilling a drop.
For more nostalgia in St. Louis, there’s Crown Candy Kitchen, a landmark diner known for its handmade malts and hefty BLTs. The spirit of Route 66 also shines at the National Museum of Transportation, which, in addition to acres of railroad equipment, displays classic cars and features a replica facade of the 1941 Art Deco-style Coral Court Motel, a Route 66 landmark that met the wrecking ball in 1995.
Route 66 fans in metro St. Louis also gravitate to Maplewood, a suburban community with an old-school bowling alley and other businesses that date back decades. The Route 66 Tribute Walk along three blocks of Manchester Road features sidewalk plaques that celebrate Mother Road history in the neighborhood and elsewhere in St. Louis.
Moon Route 66 Road Trip by Jessica Dunham (Avalon Travel, Hachette Book Group, $21.99, 366 pp.) is the ultimate guidebook to Route 66. Following the Mother Road from Chicago to Santa Monica, the guide is packed with details on lodging, local eats, famous landmarks and roadside attractions. Loaded with 38 maps, dozens of color photos and stories of the highway’s colorful lore, this guide in the Moon series is the perfect companion for getting the best from a Route 66 road trip.