It was the spring of 1837, and Robert Hill had a problem. It was his job to persuade his neighbors in his Cook County voting precinct to fulfill their responsibilities to work on the roads that passed through the area. One road was an almost purely local trail that ended—or began, depending on your perspective—at Hill’s claim. The other was a minor branch of the Chicago to Naperville Road, itself part of the system of main thoroughfares to Ottawa and Galena.

The web of trails, traces, and roads leading from Chicago on Lake Michigan to the prairie hinterland as settlement in northern Illinois began is evident from Albert Scharf’s 1900 map.
In those days before state and federal tax support of road construction and maintenance, local government required residents to work on the growing system of primitive roads that, like a spider web, spread westward from Lake Michigan to the Mississippi River.
The network of trails used by Native Americans in the area bounded by Lake Michigan and the Fox River Valley probably evolved from game trails. When Europeans arrived in the area, they continued to use the existing trail system, even though, as one historian suggested, the trails were often not the most direct routes from point to point. With their twists and turns, they were often hard to follow. Names like Vincennes Trace and Potawatomi Trace suggest the trails were little more than faint tracks through the prairies and groves that dotted northern Illinois. Even experienced guides frequently got lost.
But during the settlement era—the 1820s to the 1840s—overland routes were the only options for travelers between Lake Michigan and the head of navigation on the Illinois River at Peru and Ottawa. Not until the Illinois & Michigan Canal linked Chicago’s lakefront with the head of navigation on the Illinois River and rail lines began stretching west of Chicago in the late 1840s was overland transport by road eclipsed.
In addition, merchants and other business owners in and around the booming lead mining town of Galena in far northwest Illinois were interested in an overland link with Chicago that might offer an alternative to expensive, relatively slow river transport of food, equipment, and other supplies the growing area required. While river transport was satisfactory for bulk cargoes, the Mississippi River of those years was a sometimes fickle transportation route. Drought often closed off portions of the river to navigation. High water sometimes did the same as the primitive steamboats of the day struggled upstream against the raging current while trying to dodge a variety of hazards, from snags to shifting sandbars. And even the mighty Mississippi often froze over during the winter months.

Chicago, as seen in this view from Lake Michigan in 1820, boasted little more than Fort Dearborn and a few fur traders’ cabins scattered along the North and South Branches of the Chicago River. Two decades later, it would be an incorporated city, the largest in northern Illinois.
Beginning in the early 1830s, as settlement accelerated in the region around the southern tip of Lake Michigan, both the state and local governments in Illinois began to lay out an official system of roadways. In northern Illinois, the initial purpose of this fledgling road net was to connect the areas south and west of Lake Michigan with Chicago and its Great Lakes links with Eastern markets.
Shipping from the east via the Great Lakes to Chicago had slowly increased since the visit of the first steamboats carrying troops during the Black Hawk War in 1832. But a major problem existed; there was no harbor at Chicago. The Chicago River entered the lake at an acute angle, running parallel to the shoreline, with a sandbar blocking entrance of the river to ships on the lake. As a result, ships had to anchor offshore and transship their cargoes over the bar in small boats. It was, time-consuming, labor-intensive, and became downright dangerous to ships and crews when storms howled out of the north and west, threatening to drive unwary vessels ashore. As a result, while steamers first visited Chicago in 1832 to drop off their cargoes of U.S. Army troops, they left as soon as they were unloaded because there was no sheltered anchorage for them.
Realizing the settlement’s strategic advantages, the U.S. Government began the creation of a true port at Chicago in 1833 by cutting a channel through the sandbar at the mouth of the Chicago River. Construction started July 1, supervised by Maj. George Bender, 5th U.S. Infantry. Bender began with setting a series of piers through the sand bar that blocked the harbor mouth. The deceptively simple task of cutting a channel through the bar—and then making sure it stayed open—proved a lot more difficult than originally thought. It eventually took some six years, and a cost more than $100,000 (nearly $3 in today’s dollars) to get the job completely finished.

The proposed improvement of a channel through the sandbar at the mouth of the Chicago River. When it was finally completed, the channel helped fuel Chicago’s explosive growth.
But on Saturday, Feb. 15, 1834, with only a rudimentary channel carved through the sandbar, Mother Nature took a small hand in creating the Chicago Harbor. A heavy, two-day rainstorm caused the Chicago River to suddenly rise by three feet. The outflow of storm water found the channel Maj. Bender had begun and on which Lt. James Allen was then working, and cut a 30-foot wide, 12-foot deep channel through the bar. It’s likely the astonished engineers could hardly believe their good fortune.
On May 4, the Michigan, a sidewheel steamer with a fore-and-aft sail rig, took advantage of the new channel, and became the first steamboat to enter the Chicago River harbor, passing under the recently completed Dearborn Street drawbridge to anchor along the riverbank.
For the first time, with the channel finally cut through the bar, ships didn’t have to unload their cargoes immediately and flee to an area where there was some shelter. Instead, ships could be moored at docks along the river, safe from sudden storms, while cargo was unloaded.

The Michigan was the first ship to make its way through the sandbar at the mouth of the Chicago River and dock in the city.
Just a couple months after the Michigan arrived in Chicago’s new harbor, the aptly named Illinois became the first sailing ship to enter the Chicago River under full sail. On July 12, 1834, the Illinois forged through the newly opened channel with “her top-masts covered with flags and streamers,” sailing up-river through the open Dearborn Street drawbridge to dock at Newberry & Dole’s riverbank wharf.
While work to improve the channel through the bar and keep it from refilling with sand would continue for several years, the arrival of those first Great Lakes freighters was an important start.

The Dearborn Street drawbridge—the first of many that would be built in Chicago—raises to let a ship through to dock along the Chicago River in 1834.
The tonnage of goods shipped to and from Chicago skyrocketed almost immediately after the safe harbor was provided for arriving vessels. In 1833, the year work on the channel through the bar began, just four ships arrived at Chicago—two brigs and two schooners, but no steamboats. Just two years later, 250 ships arrived and a year after that, the number of arrivals had nearly doubled to 456 vessels, with the total including 49 steamships.
In addition to goods, people were also arriving at the new port, as more and more pioneer farmers used the Great Lakes route to travel west. After arriving, these pioneer families left Chicago’s swampy streets and settled on the Illinois prairies in the fast-developing city’s hinterland. Meanwhile, a growing volume of cargo awaited shipment east. Goods crowding the docks along the Chicago River included steadily increasing amounts of grain produced as the acreage of cultivated prairie rapidly expanded in northern Illinois.
In 1837, four years after the channel through the bar at the mouth of the Chicago River was begun, only 100 bushels of grain were shipped from Chicago via the Great Lakes. A decade later—and a year before the completion of the I&M Canal and commencement of construction of the first railroad west of the city—more than 2.2 million bushels of grain were shipped from Chicago. Each and every bushel of that grain arrived at Chicago thanks to the network of roads extending into the growing city’s hinterland.
That spider web of roads stretching northwest, north, and southwest of the city provided the means for the coming tsunami of growth that would propel the Chicago metropolitan region that was then supercharged by completion of the old-technology I&M Canal and the new-technology rail lines that followed the old traces and trails out of the city by the lake.