By Jorge Casuso

April 6, 2026 -- The famous piers in Santa Monica and Chicago were joined together last month as the symbolic start and finish of the nation's most legendary highway -- Route 66.

On March 25, Chicago City officials formally designated Navy Pier as the new symbolic starting point of the more than 2,400-mile road that is celebrating its 100th anniversary this year.

The ceremony held at Navy Pier’s South Dock, where city officials unveiled a new Route 66 starting point sign, was attended by Navy Pier CEO Marilynn Gardner and Santa Monica Pier Executive Director and Historian Jim Harris.

"Route 66 has long represented connection and possibility, and we're proud that its journey now begins at Navy Pier," Gardner said.

"As Chicago's front porch and a gateway to the city, Navy Pier is a fitting starting point to honor 100 years of American history, culture, and travel."

“Route 66 represents freedom, exploration, and the spirit of the American road trip,” Harris said.

“As Chicago establishes this exciting new starting point at Navy Pier, we are proud to continue welcoming travelers to Santa Monica -- where the journey reaches its unforgettable conclusion at the edge of the Pacific Ocean.”

While both now have symbolic signs where tourists can flock to have their pictures taken, the Chicago and Santa Monica piers are not the geographical starting and ending points of the highway celebrated in movies, writings and song.

In Chicago, the original staring point was the intersection of Adams Street and Michigan Avenue, across from the Art Institute, while the end point in Santa Monica was the intersection at Lincoln and Olympic boulevards.

If Chicago was always the designated starting point of what is affectionately known as The Mother Road, Santa Monica was not initially its designated destination.

Instead, it was at 7th Street and Broadway in downtown Los Angeles, according to a recent post by the Santa Monica Conservancy tracing the history behind the highway's final stretch to the Pacific.

And it was retired New York businessman George B. Dickinson, who moved with his wife to Santa Monica in 1912, who was largely responsible, according the Conservancy article by Steven Warnick.

After becoming vice-president of the United States Good Roads Association and General Counsel of the U.S. Highway 66 Association, Dickinson logged "thousands of miles in his big black Cadillac La Salle to rally national support for a Santa Monica extension."

In November 1929, Dickinson organized Santa Monica Highway Day, "a dramatic auto caravan from Needles to the sea as a publicity showcase for the proposed Route 66 extension," according to the article based on an unpublished manuscript by Planning Commissioner Nina Fresco.

"Tragically, on the morning of the caravan, Dickinson died of a heart attack at his home," Warnick wrote. "He was 69 years old. The caravan carried on in his honor."

But the plan to mark the end of the highway with signs along Santa Monica Boulevard ending at Palisades Park hit a roadblock when State officials turned down a destination that failed to connect with another U.S. Highway.

In 1936, after funding under the New Deal for a highway junction at Lincoln and Olympic Boulevards was approved, Santa Monica officially became the “End of the Trail,” which is proclaimed on a sign at the Pier.

"The Santa Monica Pier has long served as the symbolic western terminus," Pier official said.

The Chicago Pier's path to achieving a symbolic status was far more mundane and tenuous.

According to ABC 7 Chicago, "The CEO of Harry Caray's restaurant group helped kick off the effort" to move the starting point "in part because of Chicago's Hall of fame baseball broadcaster Harry Carey's ties to the road."

"Harry grew up on Route 66 in St. Louis (and) he drove to announce his very first game ever up Route 66 to Wrigley Field," said Grant DePorter CEO of the restaurant group that now has a Route 66 sign outside its Navy Pier door.

In an editorial, the Chicago Tribune weighed in on the different approaches taken by the two cities.

"The Los Angeles addition was pretty much a straight line a few hundred yards to the water," the editorial board wrote.

"Chicago’s version looks more akin to gerrymandering, which we are on record as opposing," the Board said, adding, "We’ll make an exception for Route 66."