Get ready to hit the road on the highway that “winds from Chicago to LA, more than 2,000 miles all the way.” In 2026, Route 66, one of America’s first highways, celebrates its 100th anniversary. And Navy Pier has been officially recognized as the eastern gateway to the Mother Road that leads all the way to Santa Monica Pier in California.
Discover how Navy Pier is leading the way in creating iconic, unforgettable experiences for locals and tourists.
Creating authentic heritage tourism experiences
Preserving and championing Route 66 is about community pride and authentic heritage tourism. Giving people a story they can actually feel.
In a world of cookie-cutter travel, legacy is the ultimate differentiator. That’s the soul of Choose Chicago’s “Never Done. Never Outdone.” campaign, which captures that relentless Chicago spirit and packages it for a global audience.
Leveraging cultural touchstones in tourism marketing
Communities along this historic highway are gearing up to welcome visitors from across the U.S. and around the world. Travelers can explore iconic landmarks, classic diners, quirky roadside attractions, and the stories that made Route 66 a legend. These experiences show the power of connecting visitors with authentic local culture and heritage—a lesson DMOs can apply in any destination.
Take the 20th anniversary of Pixar’s Cars in 2026. Fans will recognize Fillmore, the hippie van inspired by real-life Route 66 artist Bob Waldmire and voiced by comedian George Carlin. Pontiac, Illinois, honors his legacy with his Volkswagen van and “land yacht,” which he used to travel the Mother Road. These cultural touchstones turn history into storytelling that resonates with travelers, sparking both curiosity and emotional connection.
You don’t have to reinvent the wheel to get people to visit; you just have to look at what’s already parked in the driveway and highlight them (e.g., historic figures, local artists, culinary icons, or pop culture connections). By weaving authentic stories and cultural touchpoints into campaigns, destinations can create experiences that feel unique, meaningful, and memorable.
Just as Route 66 communities leverage history, film, and local legends to draw visitors, other destinations can build campaigns around the people, stories, and places that already make them special.
Navy Pier takes the lead
In a historic move, the City of Chicago will formally recognize Navy Pier as the starting point of Route 66. Mayor Brandon Johnson said, “From the shores of Lake Michigan to the Pacific Ocean, Route 66 represents the ultimate American journey.” The official dedication ceremony is set for March 25, 2026. We hope to see you there!
The designation was approved by the Chicago City Council, with 42nd Ward Alderman Brendan Reilly adding, “Route 66 has always been about dreams and possibility. Designating Navy Pier as the eastern terminus honors Chicago’s historic role while creating a powerful Pier-to-Pier connection that captures the true spirit of the American journey.”
Since 2009, the endpoint of Route 66 has been Santa Monica Pier in California. With the starting point now at Navy Pier, the road officially runs Pier to Pier—from Lake Michigan to the Pacific Ocean. A new Route 66 sign will mark the “Beginning of the Trail,” giving travelers an iconic launch point for their adventure.
Check out our interview with Choose Chicago CMO to learn how the city achieved a record-setting tourism year in 2025, and how integrated campaigns like “Never Done. Never Outdone.” are shaping the future of Chicago travel.
