Our Iowa Heritage: Lyman Dillon – Plowing the Straight & Narrow.

In 1838, when Iowa became a U.S. Territory, there were less than 23,000 people in the entire region. The map above indicates that most of Iowa was comprised of either rich prairie-land (yellow) or forested woodlands (green), with countless creeks and rivers winding their way southward toward the Mississippi River. Transportation, at the time, was pretty much limited to waterways, via canoe or raft, or by walking and/or riding by horse or mule on the limited number of trails that had been cut through the prairies by Native Iowans.

1838-1840 Building a Road from Dubuque to the Iowa/Missouri Border.

John Pulmbe’s map of the surveyed section of Iowa Territory in 1839.

When Robert Lucas, the former governor of Ohio, was appointed as Iowa’s first territorial governor, one of his highest priorities was connecting Iowans with each other and the outside world. In Ohio, Lucas advocated a forward-looking transportation system through the building of canals, so now, as Iowa’s new governor, he envisioned a similar plan, only this time by developing a network of roads that would connect Iowa’s growing communities from north to south. And, with Iowa City being at the center of that network, the focus was to build reliable roads that would lead in and out of our new capital city.

W.W. Chapman – Iowa’s first Territorial Delegate to the U.S. Congress.

Lucas’ idea for a road stretching from north to south across the Territory was delivered to the U.S. Congress in Washington by W. W. Chapman, Iowa’s first delegate in 1838. Congress recognized the need for roads but some members were reluctant, so Chapman designed his proposal to win over the opposition by adding the wording of 1) “military roads,” meaning the priority here was to aid soldiers in the transportation of supplies, and 2) the proposed road must pass through as many county seats as possible.

These two add-ons did the trick, so in December, legislation was passed appropriating $20,000 for Iowa’s first federally-funded military road, from the mining and river town of Dubuque to Keosauqua, near the Missouri border. In March, President Martin Van Buren signed the paperwork, and by summer, R. C. Tilghman, a Baltimore, Maryland engineer, was on the job, surveying Iowa Territory from Dubuque to Keosauqua.

Here is one page (edited) from engineer/surveyor R. C. Tilghman’s 1839 journal – it shows Johnson County with Iowa City to the north (labeled Seat of Government – Iowa Territory), to the south (middle of map) is “Town of Napoleon.” The black line from north to south represents the proposed Military Road, and dotted lines represent Native American trails.

To put this all in perspective, at the same time Chauncey Swan and friends were hammering a stake into the ground, marking the site of Iowa’s new capitol building, (Johnson County – May 1839), Tilghman was prepping to trek through uncharted prairies and woodlands, surveying the proposed route of Iowa’s new Military Road (see below).

Lyman Dillon of Cascade, Iowa.

Historical accounts differ here, but most reports indicate that Tilghman, as he was completing his survey of the land, laying out the map you see above, hired the Langworthy brothers (Edward, James and Lucius) of Dubuque as contractors for actually constructing the road. The brothers, in turn, contacted a young single farmer, age 39, from Cascade (Dubuque County) named Lyman Dillon to do the dirty work of plowing up a guiding furrow between Dubuque and Iowa City, marking Tilghman’s route for road crews to follow.

Beginning just outside Dubuque, in the fall of 1839, Dillon took a large sod-breaking plow with a team of five oxen, a horse-drawn covered wagon for provisions, and under the guidance of an army engineer, began plowing up what later would become known as Dillon’s Furrow86 miles – at $3 per mile.

Oxen have been found capable of plowing about ten miles a day. Although this ground had never been cleared, it has been estimated that Dillon’s operation took about ten days to complete.

Dubuque to Cascade, Monticello to Anamosa, Martelle to Mt. Vernon, from Solon into the new Capital City – Iowa City.

If you’ve ever driven this route (Hwys 1 and 151), particularly before the highways were widened and straightened, you can easily see that the rugged terrain Dillon was assigned to plow through was anything but easy. Edmund Booth, a pioneer from Anamosa, wrote in an 1839 letter:

We found a newly-broken furrow along one side of the (military) road, which, by the way, was merely a track through the grass of the prairies, and a mound of turf raised three to four feet high at intervals of a half mile, more or less.

These “mounds of turf” mentioned in Booth’s letter were, indeed, the lasting work of Lyman Dillon, marking the course of Tilghman’s original survey for road crews to use as they built the first section of Iowa’s Military Road.

As Dillon finished his work, crews came behind him, cutting trees and brush in a 40-foot wide swath. Tree stumps were grubbed out by oxen; ditches were dug to drain wetlands; and bridge abutments were built of stone, marking the best sites for future bridges and ferries. By 1840, the Military Road was in place, opening up a wide roadway for wagons and stagecoaches in and out of Iowa City.

Grant Wood’s Salute to Lyman Dillon.

Breaking the Prairie Sod, Grant Wood. This massive mural was created by Iowa’s own Grant Wood in 1936-1937. In the background of this mural, is a man plowing up the ground using a team of five oxen. Grant Wood, who hailed from Anamosa, Iowa, was obviously offering a tip of the hat to Lyman Dillon, the Cascade man who first broke the prairie sod between Dubuque and Iowa City in 1839.

So…Who is Lyman Dillon?

Lyman Dillon was born in Utica, NY on June 12, 1800. He and his brother were orphaned at a very young age and Lyman was “bound out” (adopted) to a tavern-keeper who worked him very hard, giving him little time for education or access to books.

Eventually, Lyman ran away, attending college in Utica, but soon followed the mantra of the times, “Go west, young man, go west” and, in 1836, came to Cascade (Dubuque County), locating here because of the many possibilities offered by water power and agriculture.

Lyman was 39 years old and single when he plowed his famous furrow (1839). For his ten days of labor he was paid $258 ($3 per mile), so he took the money, bought a track of land (40 acres) about two miles north of Cascade on the north fork of the Maquoketa River, opening a sawmill that complimented his farming interests. He also married Charlotte Winchell (born April 25, 1820 in Binghamton, Broome County, New York) that next year (April 12, 1841). Amazing what a little money can do for you, don’t you think?

Lyman went on to be involved in many other Dubuque County events, serving on the Dubuque County Board of Supervisors from October 1847 to August 1851. He was also elected to represent Dubuque County in the Fourth Iowa General Assembly in 1852.

Dillon’s Furrow – What It Accomplished…

Plowing the Dillon Furrow” by Shirley Shotwell (1958) – In 1921, The Palimpsest Magazine ran several stories about The Military Road. One interesting article, Phantoms on the Old Road by Marcus L. Hanson, told of his 1920 adventure retracing Dillon’s Furrow. Read it here.

With ten days of hard labor (the fall of 1839), breaking up the Iowa prairie while laying down a guide path for road crews to follow, Lyman Dillon earned $258. Not much when you compare it to the $20,000 of federal funding given Iowa for its Military Road from Dubuque to the Missouri border. Yet, the fruit of his labor quickly paid off. By the fall of 1840, the road was completed, and now there was easy access into Iowa City from both the north and the south.

While originally called Iowa’s Military Road, it was rarely used as such, and soon became better known as The National Road, part of the well-worn trail used by thousands to go west between 1840 and 1856 (when the railroad finally reached Iowa City). Without a doubt, The National Road became an important thoroughfare for pioneer families west bound from Chicago to the frontier capitol in Iowa City.

Numerous markers have been placed in Iowa cities that were connected by the work Lyman Dillon and others did in building Iowa’s Military Road. A marker in Dubuque notes that the road, which started in Dubuque, passed through Cascade, Monticello, Langworthy, Anamosa, Mt. Vernon, Ivanhoe, Solon, Iowa City, Ainsworth, Crawfordsville, Mt. Pleasant, Hillsboro, ending in Keosauqua.

Today, Dillon’s Furrow has become US Highway 151(Dubuque to Anamosa) and State Highway 1 (Anamosa to Iowa City).

Lyman & Charlotte Dillon, married in 1841, had two daughters, Cordelia Dillon Crawford (1844-1895) and Lyma Dillon Parrott (1857-1899). Lyman died on December 8, 1857 (age 57), and Charlotte died April 22, 1890 (age 69). Both are buried in Cascade’s Community Cemetery: section A, row 22, lot 321.

Here’s to Iowa’s own ground-breaker (literally), Lyman Dillon, and his bride, Charlotte. You both arrived in Iowa in the mid-1830’s and helped make our state what it is today! Godspeed!


Kudos to the amazing resources below for the many quotes, photographs, etc. used on this page.

Remnant Prairie: A closer look at Iowa’s rarest landscape, Katy Heggen, Iowa Natural Heritage Foundation, August 24, 2017

The Old Military Road, John C. Parish, The Palimpsest, Volume 2-Number 2-Article 2, February 1921, pp 33-34

Lyman Dillon, Encyclopedia Dubuque

Military Road, Encyclopedia Dubuque

Postcard 262: Iowa City’s First Federal Aid Highway – in 1839, Bob Hibbs, IAGenWeb-Johnson County, September 18, 2004

R. C. Tilghman’s journal (edited), Indian Look-Out – Below Iowa City, David Goodwin, The Palimpsest, Volume 54 – Number 1 – Article 4, January 1963, p 24

Lyman Dillon and the Military Road, Tri-County Historical Society

IC History: Iowa City’s early crossroads, Marlin Ingalls, Little Village Magazine, July 8, 2003

Representative Lyman Dillon, The Iowa Legislature

On The Trail of Lyman Dillon, Douglas Monk, Facebook

On The Trail of Lyman Dillon – OnLine Journal, Douglas Monk, WordPress blog

Phantoms on the Old Road, Marcus L. Hansen, The Palimpsest, Volume 2-Number 2-Article 3, February 1921, pp 35-48

Breaking the Prairie Sod, Grant Wood, SUI University Museums, 1936-1937

Grant Wood Murals – Breaking the Prairie Sod, ISU Museums, YouTube video

Lyman Dillon, Find-A-Grave

Charlotte Winchell Dillon, Find-A-Grave

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