Once the dust settled in 1926, Cyrus Avery wrote a polite thank-you letter to the federal highway official who had helped end a fight that dragged on for months. Near the end, he mentioned the U.S. 60 shields. He would, he said, “have to junk them.”
That number never went up on the road he’d pushed for. The Chicago-to-Los Angeles highway got a leftover instead — and the leftover became the most famous highway number in America. The Route 66 centennial lands on November 11, 2026, a hundred years to the day after state highway officials adopted the U.S. numbered highway system that put “66” on the map.
The birthday gets the parades. The fight over the number is the better piece of Route 66 history, and it explains why the Mother Road carries a number that broke the system’s own rules.
Why the Chicago–Los Angeles Road Was Supposed to Be 60
The 1926 plan came with a pecking order everyone grasped right away. Two-digit routes ending in zero — 20, 30, 40, 50 — were the long east-west lines, and highway boosters read a zero (or a 1) as a first-class road. Any other number felt secondary.
By that logic, 60 belonged to a straight coast-to-coast route between U.S. 50 and U.S. 70. Instead, the committee drawing the map handed it to a diagonal crescent from Chicago to Los Angeles. Three of the five committee members, Avery among them, represented states that crescent ran through. A Federal Highway Administration history of the episode calls the exception “suspicious.”
A Governor Who Read the Map
Kentucky’s governor, William J. Fields, noticed. On the new map, zero routes marched toward his state from the north and the south — and 60, which should have crossed Virginia, West Virginia and Kentucky, was sitting in Chicago.
On December 8, 1925, he announced that Kentucky would ignore the proposed U.S. highway numbers. “Chicago influence is written all over the map,” he said. Kentucky’s complaint came down to one line: it was the only Mississippi Valley state without a route number ending in zero.
How Did 62 Become 66?
The first compromise didn’t hold. At a meeting in Chicago in January 1926, Avery said one number running all the way from Chicago to L.A. mattered more to him than whether it was 60 or 62. The committee kept 60 on his road and offered Kentucky 62, with a swap held in reserve. When Kentucky refused, federal officials made the swap — 60 through Kentucky, 62 for Chicago to Los Angeles.
Avery, it turned out, did care. On February 10 he “strenuously objected” by telegram. B. H. Piepmeier, chief engineer of Missouri’s State Highway Commission, refused 62 and a split-number idea after it, and Kentucky rejected that one too. For weeks, nobody moved.
The Afternoon in Springfield
The way out turned up on April 30, 1926, in Springfield, Missouri. Avery met Piepmeier there, and Oklahoma’s chief highway engineer, John M. Page, spotted something nobody had claimed: the number 66 wasn’t assigned to any route. The Federal Highway Administration’s own history of the numbering fight, “From Names to Numbers,” quotes the telegram the two men sent that afternoon: “We prefer sixty six to sixty two.”
It wasn’t final yet. Kentucky signed off in July, and the whole system, U.S. 66 included, was adopted that November 11. The April telegram is why Springfield bills itself as the birthplace of Route 66. The road itself was shorter than people picture, too — in 1926 it ended in downtown Los Angeles, and the western end didn’t reach Santa Monica until 1936.
Nobody in that Springfield meeting could have guessed what the double six would turn into. It’s on neon signs, painted pavement, jacket patches and belt buckles. Biker jewelers sculpt it as well — one sterling silver Route 66 motorcycle helmet ring sets the shield on the side of a vintage helmet, with brass goggles and a cigar on the rider’s face. A number picked because it was spare now stands in for the whole open road.
Riding It in November? Check the Altitude First
A centennial ride on the actual birthday sounds right. The calendar is the catch. November 11 sits at the edge of the season when the western half of the route can turn on you, and the reason is altitude more than latitude.
Flagstaff, Arizona, right on the old road, sits at around 7,000 feet, according to the National Weather Service. Snow there doesn’t wait for deep winter: over Thanksgiving weekend in 2019, a storm left about 17 inches of snow at the NWS office in Flagstaff and caused road closures across northern Arizona.
