June 3, 2026
Route 66 sign on Santa Monica Pier in Santa Monica, CA.
The "Pier to Pier" event will unite Santa Monica, Chicago this weekend

Two piers are better than one!

In a rare coast-to-coast celebration, two of America’s most iconic waterfront landmarks — the Santa Monica Pier and Chicago’s Navy Pier — will unite this Saturday, June 6, for a one-day “Pier to Pier” event marking 100 years of the legendary Route 66.

The synchronized celebration kicks off at 10 a.m. local time in both cities, with a fitting tribute to the highway’s 2,448-mile journey: 66 minutes of free rides on two landmark Ferris wheels. In Santa Monica, guests can hop aboard the solar-powered Pacific Wheel at Pacific Park, while Chicago visitors will ride the Navy Pier Centennial Wheel overlooking Lake Michigan.

The event highlights the historic connection between the two cities — Chicago as the symbolic starting point of Route 66 and Santa Monica as its famed western terminus, marked by the “End of the Trail” sign on the pier.

“Like Navy Pier, Route 66 has always represented adventure, discovery, and the spirit of exploration,” says Marilynn Gardner, President and CEO of Navy Pier. “We’re proud to join Santa Monica Pier in celebrating the road that has connected generations of travelers.”

Santa Monica Pier Executive Director and historian Jim Harris called the celebration a tribute to “history, nostalgia, and the timeless excitement of reaching the end — or beginning — of America’s most famous highway.”

 

The beginning of Route 66 on Navy Pier in Chicago
The beginning of Route 66 on Chicago’s Navy Pier.

Free rides for both Ferris wheels will be available from 10 to 11:06 a.m. to guests who RSVP in advance, with limited capacity. Riders during the 66-minute window can also purchase commemorative photos for $6.

The June 6 celebration follows a full week of Route 66 festivities in Santa Monica, including a city-hosted festival at the pier on Thursday, June 4, from 4 to 8 p.m.

The event will also feature live country music, line dancing, and a showcase of classic cars curated by the Petersen Automotive Museum.  Santa Monica Brew Works will debut its new “End of the Trail Pale Ale,” while Amarillo’s famed Big Texan restaurant will stage its signature 72-ounce steak challenge — with Santa Monica’s police and fire chiefs set to take on the oversized meal.

“This is exactly the kind of event that makes Santa Monica special,” says Fire Chief Matthew Hallock. “It’s about celebrating history, connecting with the community, and having a lot of fun along the way.”

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Sean Daly