From its earliest days, Chicago owed its wealth—in fact, its very existence—to transportation. The Lake Michigan water highway, plunging deep into the interior of North America, brought the earliest French explorers to the Chicago portage. Throughout the colonial and pioneer era, the lake acted as a north-south superhighway for traders, soldiers, and settlers.
But while Lake Michigan penetrated deeply into what would one day become the Midwest, there was no direct link from the lake to the vital Mississippi-Ohio river system. The sluggish Chicago River emptied into the lake amid marshes and sand dunes, but it did not, except during floods, connect with any of the south-flowing rivers in the area. Instead, the earliest travelers paddled their canoes up the Chicago River to the overland portage to the Des Plaines River. From there, the route flowed south to the confluence with the Kankakee River where the Illinois River forms and then down to the Mississippi.
While that route was passable—for most of the year—for canoes and small boats, it was totally unsuitable unusable for steamboats. Instead, the head of steam navigation on the Illinois River during periods of high water was Ottawa. During the rest of the year when the river was shallower, Peru was as far as the steamboats of the 1820s and 1830s could get.
Because of this gap in water transportation from the lake to the Illinois, the road from Chicago to Ottawa was a major economic engine driving development, both in Chicago and its hinterland throughout northern Illinois.
The branch of the Chicago to Ottawa Trail known as the High Prairie Trail was probably first used by the region’s Native American inhabitants. While the Indians’ permanent villages were located along the Fox River and other area streams, winter family hunting camps were scattered along the banks of the Illinois River. It’s likely the trail from the lakeshore at Chicago to Ottawa was forged by these groups as they made their fall trips to the Illinois and spring journeys back to the Fox, DuPage, and DesPlaines rivers.
In the late 1820s when white settlement began in earnest in northern Illinois, the overland route from Chicago on the lake to Ottawa became economically significant. Goods were sent by steamboat up the Illinois and offloaded at either Peru or Ottawa for overland shipment to Chicago. In return, the growing variety of goods, ranging from timber cut and milled in Wisconsin and Michigan forests to grain and livestock grown by farmers in Chicago’s outlying area was shipped back south to be transported down the Mississippi to the Gulf of Mexico.
As it evolved, the trail from Chicago to Ottawa consisted of three main branches, the eastern, central, and western. Two of the three—the western and central branches—passed through Kendall County. The eastern branch followed the course of the DesPlaines-Illinois River, looping about 10 miles east of Kendall County’s borders.
The central branch, called the High Prairie Trail, was the most heavily traveled. The northern stretch of the High Prairie Trail was established in 1831 by the Cook County Board during the county’s first year of existence. Cook originally included all of today’s Cook and DuPage counties, plus most of Will. The county road paralleled and sometimes directly followed today’s Odgen Avenue (U.S. Route 34) from downtown Chicago to Bernard Lawton’s inn and tavern at the DesPlaines River ford (at today’s Riverside), and from there in an almost direct route southwest to Walker’s Grove (today’s Plainfield) at the DuPage River ford. From there, the road followed a series of moraine ridges across the prairie into LaSalle County (then including all of LaSalle, Kendall, and Grundy counties, plus all the land north of there to the Wisconsin border) where it ran southwesterly through what would one day be Plattville and Lisbon to the tiny Holderman’s Grove settlement and then on to Ottawa.
For the first two years of the official route’s existence, there was only the occasional traveler on the road to stop at Abraham Holderman’s tiny inn at the southern tip of Big Grove. But in 1833, things began to pick up. That year, Dr. John Taylor Temple was granted the U.S. Post Office’s contract to carry mail from Chicago on the High Prairie Trail via Plainfield and Holderman’s to Ottawa, where it would be sent by steamboat to St. Louis. Meanwhile, mail that had come north by riverboat would be carried northeast up to the port of Chicago.
Temple’s first coach clattered out of Chicago on Jan. 1, 1834, with an ambitious young lawyer, John Dean Caton, at the reins.
News that Temple’s new stage line would start carrying mail and passengers spread quickly. Traveling the new road from Chicago southwest in 1833, Daniel Platt of New York (his family had established Plattsburg) arrived in what would one day become Kendall County and established an inn at Plattville, while Levi Hills and family, more New Yorkers, arrived and bought Holderman’s inn. A year later, Hills hitched up several yokes of oxen and using logs as rollers moved the log tavern out of its grove out onto the prairie to the site of what soon became the village of Lisbon, apparently to better serve stagecoach travelers.
The western branch of the Chicago to Ottawa Trail used the same route as the High Prairie Trail until it crossed the Des Plaines at Lawton’s. From there, it headed to Capt. Joseph Naper’s settlement (modern Naperville) on the DuPage. From there, the road crossed the prairie to Oswego, where it turned south and followed the Fox River to Yorkville. From Yorkville, the road turned southwest down the Fox River to the hamlet of Pavilion and then to the Hollenbacks’ settlement at Newark before joining the High Prairie Trail just north of Ottawa.
Today, the western branch of the Chicago to Ottawa Trail is still an economic engine for Kendall County. The U.S. Route 34 corridor—which follows almost the exact course of the historic old road—has spurred the growth of towns along its route due to its direct connection to Naperville and the rest of the collar counties.