The Longest Road in the U.S. Passes Through Iowa and Illinois: Trust Me, You’ve Driven It

As I set out into the world, I remember taking my first trip to college along a stretch of road I would travel so many more times over the coming years. Trips to the Cedar Falls, Waterloo, and Dubuque area seemed insignificant, despite the fact that I was actually traveling on the longest highway in the United States.

That's right, if you’re a road trip enthusiast, there’s a highway that should be on your bucket list: U.S. Route 20. Stretching 3,365 miles from Boston, Massachusetts, to Newport, Oregon, it is the longest road in the United States, offering an epic journey through 12 states. And right in the heart of this cross-country trek, Route 20 winds its way through the picturesque landscapes of Iowa and Illinois.

Now, Route 20 isn’t just long—it’s a road rich with history. Established in 1926, this highway has seen generations of travelers, from the early days of automobiles to today’s modern road trippers. While parts of Route 20 have been upgraded, much of it remains delightfully old-fashioned, providing a glimpse into America’s past and some scenic two-lane driving in some places. As Route 20 crosses Illinois and Iowa, it takes you from the flat farmlands and small towns of the Midwest to the bustling cities that have shaped the nation’s history.

Illinois: From Urban Sprawl to Historic Galena

Route 20 enters Illinois near Chicago, one of America’s most iconic cities. Here, you can experience the vibrancy of urban life, from towering skyscrapers to deep-dish pizza. But as you leave Chicago, the road quickly transitions to rolling countryside and quaint small towns.

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One of the highlights along Route 20 in Illinois is Galena, a town that feels like a step back in time. Known for its 19th-century buildings and connection to President Ulysses S. Grant, Galena offers charming shops, historic sites, and cozy accommodations, making it a perfect stop on your journey.

Iowa: Wide-Open Spaces and Small-Town Charm

Crossing the Mississippi River from Illinois brings you into Iowa, where Route 20 takes on a more rural character. The highway winds through quintessentially American landscapes—endless fields, red barns, and wide-open skies.

In Iowa, Route 20 passes through towns like Dubuque, Manchester, and Waterloo, each offering a unique slice of Midwestern life. Dubuque, perched on the Mississippi River, is one of Iowa’s oldest cities and offers stunning river views, historic architecture, and a lively arts scene.

As you drive westward through Iowa, the landscape opens up into the vast plains and farmland that defines the American heartland. These wide-open spaces offer a sense of freedom and solitude that’s perfect for those who love the open road: and then you hit Nebraska. Of course, Highway 20 may be the longest road, but it may not be the most famous. That honor goes to Interstate-80. I mean most of you know the song, right? On a long and lonesome highway east of Omaha...

Well, whether you’re a seasoned road tripper or just looking for an adventure, Route 20 offers a unique way to see the U.S. from a ground-level perspective. In Illinois and Iowa, it’s more than just a highway—it’s a journey through history, connecting the past with the present and the East with the West.

So, the next time you’re planning a road trip, consider 'tripping' down U.S. Route 20. Whether you start in Boston, Newport, or somewhere in between, you’ll experience a little bit of everything our beautiful America has to offer; and right at the heart of your trip is Iowa and Illinois.