Where is the Oldest Road in All of Iowa?

Next time you’re cruising down the highway with the radio turned up, think about the history buried right beneath the pavement. Every modern road began as a dirt trail, a wagon rut, or a pioneer path. But one specific route holds the ultimate bragging rights as the grandfather of them all in the Hawkeye State.

Carved out of the wilderness way back in 1839 to connect a booming mining town to the Missouri border, the Old Military Road isn't just a stretch of dirt and pavement, it's the oldest road in all of Iowa.

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Credit: Canva

Iowa's 'Old Military Road' dates back to the days of frontier soldiers, pioneers, and an America that was still pushing its boundaries westward. 51 years before the first automobile was ever driven in the Hawkeye State, a $20,000 act of Congress carved out the state's very first highway.

In March of 1839, Iowa was still just a territory (statehood wouldn't happen until 1846). Travel across the Midwest prairie was intense and difficult, with most pioneers and soldiers relying on old Native American trails or rough, unmarked wagon ruts. The U.S. Government was ready to establish a stronger presence across the frontier, so they authorized $20,000 (equivalent to roughly $720,000 today) to construct a "Military Road". The main goal was to create a dependable overland route to move troops, supplies, and mail.

The road was designed to start in Dubuque (Iowa's oldest city), which was a booming lead-mining town on the Mississippi River - then it would run diagonally southwest to the brand new capital of the Iowa territory, Iowa City. From there, the road would continue southward all the way to the northern border of Missouri, where it could eventually connect to St. Louis.

Ironically, the U.S. military never actually ended up using the road for major troop movements. Instead, it became a vital artery for pioneers, settlers, and stagecoaches, single-handedly ensuring the survival and growth of the towns along its path.

You don't need a time machine to travel it today, either. Much of the original path was simply paved over as the automobile era took off in the early 20th Century. If you drive modern-day State Highway 1 from Iowa City up to Anamosa, and then hop on Highway 151 from Anamosa into Dubuque, your tires are rolling right over the original path built in the Mid-19th Century.

If you want to go on a historical scavenger hunt, keep your eyes peeled in towns like Mount Vernon, Anamosa, and Mount Pleasant. You can still find large bronze plaques standing proudly near the roadside, erected in the 1930s by the Daughters of the American Revolution. This reminds travelers that they are driving on the historic 'Old Military Road'.