This route marks Day One of a multi-day journey along U.S. Route 66, tracing the first hundred miles of the historic highway through Illinois. Beginning at Navy Pier—a symbolic starting point for many travelers—you’ll follow the road southwest through a series of communities that helped define the early American road trip, ending the day in Bloomington, Illinois. Known as “The First Hundred Miles of Route 66 in Illinois,” this stretch offers an ideal introduction to the culture, history, and character that make the route enduringly significant.

There’s something different about taking the scenic route—especially when that route is U.S. Route 66.

Just an hour outside of Chicago, the landscape begins to shift. The pace slows. The road narrows. And suddenly, you’re not just driving—you’re stepping into one of the most iconic cultural corridors in American history.

This one tank trip takes you through a stretch of Illinois Route 66 where roadside architecture, local museums, and preserved landmarks tell the story of how Americans once experienced travel.

I firmly believe that too many people rush through Illinois. This is a huge mistake. The density of iconic stops between Joliet-Bloomington requires at least a full day.

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Stop 1: Joliet — Where the Journey Begins

Start your trip in Joliet, where Route 66 history meets a revitalized downtown.

Visit the Joliet Area Historical Museum, which offers a strong introduction to the region’s industrial and cultural past. Exhibits highlight everything from local history to the significance of Route 66, grounding your trip in context before you hit the road.

Take time to walk downtown—this is a place where preservation and community investment are actively shaping the future.

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Stop 2: Wilmington — The Gemini Giant

A short drive south brings you to one of the most recognizable roadside attractions in the country: the Gemini Giant.

Standing tall with its rocket in hand, the Gemini Giant is more than a photo stop—it’s a symbol of mid-century optimism, when space-age design and roadside culture intersected in uniquely American ways.

This is Route 66 at its most iconic.

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Stop 3: Braidwood — A Pause Along the Way

In Braidwood, the pace slows even further.

Small-town restaurants and local businesses reflect the kind of roadside culture that once defined long-distance travel. It’s a reminder that Route 66 was never just about the destination—it was about the places in between.

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Stop 4: Dwight — Preservation and Architectural Storytelling

Dwight offers one of the most compelling examples of preservation along Route 66.

Here you’ll find beautifully maintained historic buildings, including the Ambler-Becker Texaco Gas Station—one of the longest-operating gas stations on the route—and the Frank L. Smith Bank, designed by Frank Lloyd Wright.

Dwight demonstrates how architecture, preservation, and storytelling can work together to create a strong sense of place.

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Stop 5: Pontiac — Museums That Tell the Story

Pontiac is one of the strongest examples of how small communities are embracing Route 66 as a cultural and economic asset.

Here you’ll find the Route 66 Association Hall of Fame & Museum, along with murals, preserved buildings, and a walkable downtown filled with character.

This is where Route 66 becomes more than nostalgia—it becomes a strategy for revitalization.

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Stop 6: Lexington — Small Town, Big Story

Just north of Pontiac, Lexington is an easy stop that captures the quieter side of Route 66.

With its historic downtown, local shops, and nearby attractions like Memory Lane—a preserved stretch of original Route 66—you can quite literally walk or drive a piece of the past.

Lexington reminds travelers that some of the most meaningful experiences on Route 66 aren’t the biggest—they’re the most authentic.

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Why This Trip Matters

This stretch of Route 66 tells a larger story about American travel.

It reflects a time when the journey itself was the experience—when roads were lined with independently owned businesses, local landmarks, and places that invited you to stop, explore, and connect.

Today, these communities are reclaiming that legacy. Through preservation, storytelling, and tourism, they are creating experiences that feel both historic and immediate.

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Tips for the Road

• Plan for a half-day or full-day trip
• Take your time—this is not a drive to rush
• Talk to locals when you stop
• Look for the details: signage, architecture, and small museums

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The Scenic Route Is Still There

In a world built for efficiency, trips like this offer something different.

They remind us that meaningful travel doesn’t require a flight or a long itinerary. Sometimes, it’s just a tank of gas, an open road, and a willingness to slow down.

Route 66 is still here—and it’s still telling stories.