This Route 66 trivia quiz has 50 free questions with answers and drives the whole road: from the 1926 numbering fight that gave it its double digits and the Tulsa oilman who fathered it, through the Dust Bowl migrants of The Grapes of Wrath, the 1928 Bunion Derby footrace, the Corvette on 1960s TV and Bobby Troup's song, to the interstates that killed it in 1985 and the barbers, artists and neon-motel owners who brought it back as a National Scenic Byway. Along the way it stops at the roadside attractions every road-tripper photographs: the Gemini Giant, the Chain of Rocks Bridge, Meramec Caverns, the Blue Whale of Catoosa, Cadillac Ranch, the Big Texan's 72-ounce steak, the U-Drop Inn, the Blue Swallow, El Rancho, Wigwam Motels, the burros of Oatman and Roy's in Amboy. Pixar fans get their due too, since Radiator Springs, Mater, Fillmore, Ramone's shop and the Cozy Cone all have real Route 66 originals. Every answer has been checked against a reference encyclopaedia, and each question shows its explanation and citation once you have answered.
30 of 50 questions with answers and explanations. Play the quiz
Q 01U.S. Route 66 was established on 11 November 1926 and ran from Chicago to which western terminus?
Santa Monica
Originally it ended in downtown Los Angeles; the 1936 extension took it to Santa Monica and a junction with US 101.
Q 02How long was Route 66 from end to end?
2,448 miles
That is 3,940 km; the road crossed eight states and three time zones.
Q 03How many states did Route 66 pass through?
Eight
Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California; Kansas got only about 13 miles of it.
Q 04Which state had the shortest stretch of Route 66, about 13 miles?
Kansas
The road clipped the state's southeast corner through Galena, Riverton and Baxter Springs.
Q 05Which Tulsa businessman is known as the 'Father of Route 66'?
Cyrus Avery
He sat on the federal board that created the numbered highway system and made sure the Chicago-Los Angeles road ran through his home state.
Q 06Which number did promoters originally want for the Chicago-Los Angeles road, before Kentucky objected?
US 60
Oklahoma highway engineer John M. Page found that 66 was unassigned, and the catchy double digit stuck.
Q 07Which novelist gave Route 66 the nickname 'the Mother Road'?
John Steinbeck
In The Grapes of Wrath the Joad family flee the Oklahoma Dust Bowl along it; the book won the Pulitzer Prize.
Q 08The U.S. Highway 66 Association promoted the road under which nickname?
The Main Street of America
Its official designation was the Will Rogers Memorial Highway, after the Oklahoma humorist.
Q 09By 1938 Route 66 had achieved which milestone before any other US highway?
Fully paved end to end
Much of it had been gravel or dirt; the New Deal put thousands to work finishing the surface.
Q 10In which year was Route 66 officially removed from the US Highway System?
1985
Interstate 40 and its cousins had absorbed almost all of it; the last stretch to be bypassed was at Williams, Arizona.
Q 11The 1928 'Bunion Derby' footrace followed Route 66 from Los Angeles to Chicago before finishing where?
New York City
Andy Payne of Oklahoma won in 573 hours over 84 days, averaging six miles an hour; promoter C. C. Pyle ran it again in 1929.
Q 12Who won the 1928 Trans-American Footrace along Route 66, finishing in about 573 hours of running?
Andy Payne
The part-Cherokee farm boy from Oklahoma used the prize to pay off his family's mortgage; Salo won the 1929 edition.
Q 13Who wrote the 1946 song '(Get Your Kicks on) Route 66'?
Bobby Troup
Troup wrote it while driving west to Hollywood; Nat King Cole's trio recorded it first, and Chuck Berry and the Rolling Stones followed.
Q 21Which Route 66 character in Cars was inspired by artist Bob Waldmire's orange 1972 Volkswagen Microbus?
Fillmore
Pixar wanted to call the character Waldmire, but the artist refused to sell his name for Happy Meal toys.
Q 22The Art Deco U-Drop Inn, built in 1936 in Shamrock, Texas, appears in Cars as which character's business?
Ramone's body shop
The tower-topped gas station and café is one of the most photographed buildings on the road and was restored with a federal grant.
Q 23Wigwam Motels with tipi-shaped rooms still operate on Route 66 in Holbrook, Arizona and which California city?
San Bernardino
Q 14Which British band put a version of 'Route 66' on their 1964 debut album?
The Rolling Stones
They followed Chuck Berry's 1961 recording; the song has since been cut by everyone from Depeche Mode to John Mayer.
Q 15In the CBS series Route 66 (1960-64), Martin Milner and George Maharis roamed America in what car?
A Chevrolet Corvette
Chevrolet supplied a new Corvette each season; Nelson Riddle's jazzy theme became a hit in its own right.
Q 16Cadillac Ranch, near Amarillo, Texas, consists of how many Cadillacs buried nose-first in a field?
Ten
The Ant Farm collective built it in 1974 with money from eccentric millionaire Stanley Marsh 3; visitors are now encouraged to spray-paint the cars.
Q 17What are visitors to Cadillac Ranch encouraged to do to the cars?
Spray-paint them
They have long since lost their original colours under decades of graffiti; the artists consider the vandalism part of the work.
Q 18Pixar's Cars (2006) is set in Radiator Springs, a Route 66 town whose trade dried up when what happened?
An interstate bypassed it
Route 66 historian Michael Wallis led eleven Pixar animators down the real road in rented Cadillacs to research the film.
Q 19Which Route 66 town's barber Angel Delgadillo founded the Historic Route 66 Association of Arizona in 1987?
Seligman
Delgadillo met John Lasseter during research for Cars, and Seligman's story of losing its traffic overnight to Interstate 40 fed straight into Radiator Springs.
Q 20In which state is Galena, where the rusty tow truck that inspired Cars' Mater sits outside a Kan-O-Tex station?
Kansas
The store is called Cars on the Route; Galena sits on the state's brief 13-mile stretch of the highway.
Frank Redford began the chain in the 1930s; Sally's Cozy Cone Motel in Cars is a direct tribute.
Q 24Hugh Davis built the concrete Blue Whale of Catoosa, Oklahoma, in the early 1970s for whom?
His wife, who collected figurines
Zelta Davis got a concrete-and-iron whale on the family swimming hole; it became one of the road's best-loved landmarks.
Q 25Lester B. Dill, who opened Meramec Caverns to tourists in 1935, is credited with inventing what?
The bumper sticker
He also painted the caverns' name on barn roofs across the Midwest and rented out what he called the world's only underground billboard.
Q 26According to local legend, which outlaw used Meramec Caverns as a hideout in the 1870s?
Jesse James
Historians find scant evidence for it, but Dill leaned on the story hard in his advertising.
Q 27The Gemini Giant, a 30-foot fibreglass 'Muffler Man' in Wilmington, Illinois, is dressed as what?
An astronaut holding a rocket
He stood outside the Launching Pad Drive-In from the 1960s and was moved to a town park in 2024.
Q 28The Chain of Rocks Bridge once carried Route 66 over the Mississippi. What structural quirk is it famous for?
A 22-degree bend midway
The kink was needed to line up with the riverbed; today it carries only walkers and cyclists and doubled as the '69th Street Bridge' in Escape from New York.
Q 29How big is the steak Amarillo's Big Texan Steak Ranch gives free to anyone who finishes it in an hour?
72 ounces
Plus a roll, baked potato, shrimp cocktail and salad; failure costs $72.
Q 30Oatman, Arizona, a Route 66 stop, is best known for what wandering its streets?
Wild burros
They descend from the prospectors' pack animals; the Oatman Hotel also claims, incorrectly, to have hosted Clark Gable and Carole Lombard's honeymoon.