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This Route 66 trivia quiz has 49 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 49 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
Eight: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California, from Lake Michigan to the Pacific.
Q 04Before a 1937 realignment, Route 66 looped north through which New Mexico city?
Santa Fe
Santa Fe. Until 1937 Route 66 swung north from Santa Rosa through Santa Fe before dropping to Albuquerque; the straight westward realignment cut roughly 100 miles off the road.
Q 05Which Tulsa businessman is known as the 'Father of Route 66'?
Cyrus Avery
Cyrus Avery, a Tulsa businessman on the 1925 Joint Board on Interstate Highways, steered the Chicago-Los Angeles road through Oklahoma and earned the title 'Father of Route 66'.
Q 06Which number did promoters originally want for the Chicago-Los Angeles road, before Kentucky objected?
US 60
US 60 was the number the promoters wanted, but Kentucky insisted on a route ending in zero for itself, so the Chicago-Los Angeles road took the unassigned 66 in 1926.
Q 07Which novelist gave Route 66 the nickname 'the Mother Road'?
John Steinbeck
John Steinbeck called it 'the Mother Road' in The Grapes of Wrath (1939), in which the Joads flee the Oklahoma Dust Bowl along Route 66; the novel won the 1940 Pulitzer Prize.
Q 08The U.S. Highway 66 Association promoted the road under which nickname?
The Main Street of America
The U.S. Highway 66 Association, formed in 1927, sold the road as 'The Main Street of America'; in 1952 it also dedicated the route as the Will Rogers Highway.
Q 09Which milestone did Route 66 reach in 1938?
Fully paved end to end
Route 66 was fully paved end to end by 1938; much of it had been gravel or dirt, and New Deal relief crews finished the surface.
Q 10In which year was Route 66 officially removed from the US Highway System?
1985
Route 66 was decertified on 27 June 1985, after Interstates 55, 44, 40, 15 and 10 had absorbed nearly all of its traffic.
Q 11The 1928 'Bunion Derby' footrace followed Route 66 from Los Angeles to Chicago before finishing where?
New York City
New York City. The race left Los Angeles' Ascot Speedway on 4 March 1928 and ended 84 days later at Madison Square Garden; promoter C. C. Pyle staged a return run in 1929.
Q 12Kingman, Arizona's Route 66 main street is named for which actor raised there?
Andy Devine
Andy Devine. The gravel-voiced character actor, stagecoach driver Buck in Stagecoach (1939), grew up in Kingman, which renamed its Route 66 thoroughfare Andy Devine Avenue in his honour.
Q 13Who wrote the 1946 song '(Get Your Kicks on) Route 66'?
Bobby Troup
Q 21The 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 22Wigwam Motels with tipi-shaped rooms stand on Route 66 in Holbrook, Arizona, and which California city?
San Bernardino
San Bernardino. Frank Redford's chain began in Kentucky in the 1930s; the Holbrook and San Bernardino wigwams are its two Route 66 survivors, and Sally's Cozy Cone Motel in Cars is a tribute.
Q 23Hugh Davis built the concrete Blue Whale of Catoosa, Oklahoma, in the early 1970s for whom?
Bobby Troup wrote it in 1946 while driving west to Hollywood with his wife Cynthia, who suggested the title; the Nat King Cole Trio's recording that year made it a hit.
Q 14Which town does the song 'Route 66' name out of geographic order?
Winona
Winona. Troup's lyric runs 'Flagstaff, Arizona, don't forget Winona', yet Winona lies east of Flagstaff, so a westbound driver passes it first; the rhyme put it after.
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
Ten Cadillacs, model years 1949 to 1963, were half-buried nose-down by the Ant Farm collective in 1974 with money from Amarillo millionaire Stanley Marsh 3.
Q 17Route 66 crossed which desert between Needles and Barstow, California?
Mojave
The Mojave Desert. West of the Colorado River crossing at Needles, Route 66 ran some 140 miles across the Mojave to Barstow, the stretch drivers dreaded most in summer heat.
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
An interstate bypassed it. In Cars, Radiator Springs withers once Interstate 40 pulls drivers off Route 66, a fate the film's crew saw in real towns while touring the road with historian Michael Wallis.
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 20Which Route 66 character in Cars was inspired by artist Bob Waldmire's orange 1972 Volkswagen Microbus?
Fillmore
Fillmore, the hippie VW bus, was modelled on Waldmire's Microbus; Pixar wanted to name him Waldmire, but the artist, a vegetarian, declined to have his name on Happy Meal toys.
His wife, who collected figurines
His wife. Davis built the whale as an anniversary gift for Zelta, who collected whale figurines, on the family's swimming pond; it opened in 1972 and became a beloved landmark.
Q 24Lester B. Dill, who opened Meramec Caverns to tourists in 1935, is credited with inventing what?
The bumper sticker
The bumper sticker: Dill had staff tie Meramec Caverns signs to visitors' bumpers, then switched to adhesive cards; he also painted the caverns' name on barn roofs across the Midwest.
Q 25According to local legend, which outlaw used Meramec Caverns as a hideout in the 1870s?
Jesse James
Jesse James. Dill promoted the caverns as the James gang's 1870s hideout, a claim historians find little evidence for, but it drew tourists for decades.
Q 26The Gemini Giant, a 30-foot fibreglass 'Muffler Man', stands in which Illinois Route 66 town?
Wilmington
Wilmington. The astronaut-suited Gemini Giant went up outside the Launching Pad Drive-In in the 1960s and was moved to a Wilmington park in 2024.
Q 27What structural quirk made the Chain of Rocks Bridge, Route 66's Mississippi crossing, famous?
A 22-degree bend midway
Its 22-degree bend midway, forced by the need to set piers on bedrock while leaving barges a clear channel; the 1929 bridge later became a walking and cycling path and appeared in Escape from New York (1981).
Q 28How big is the steak Amarillo's Big Texan Steak Ranch gives free to anyone who finishes it in an hour?
72 ounces
72 ounces, a four-and-a-half-pound steak that must be finished within an hour along with a shrimp cocktail, baked potato, salad and roll; those who fail pay for the meal.
Q 29Oatman, Arizona, a Route 66 stop, is best known for what wandering its streets?
Wild burros
Wild burros. The donkeys descend from pack animals turned loose by gold prospectors when Oatman's mines closed; they roam the main street begging food from tourists.
Q 30Which Arizona Route 66 town built a 'Standin' on the Corner' park after the Eagles' 'Take It Easy'?
Winslow
Winslow. The 1999 park's statue and mural illustrate the lyric 'standin' on a corner in Winslow, Arizona'; the town's other jewel is La Posada, Mary Colter's 1930 Harvey House hotel.