US-20 angles across northern Illinois from the Mississippi River to Lake Michigan, bringing you from the unglaciated scenery of the Driftless Region to the towering city of Chicago in less than 200 miles.

The western stretches pass through hill-and-valley regions where water power and mineral deposits were harnessed by early industry. Especially around Galena, the old two-lane road is still in use, climbing onto stony ridges, then dropping into hardwood-forested valleys across the undulating region that stretches east from the Iowa border. This stretch of old road, officially named and signed as the General Grant Highway, has as great a variety of barns and grain bins as anywhere in the country. However, there’s considerable pressure to widen and “improve” it into a four-lane freeway, so enjoy it while you can.

Map of the Oregon Trail through Illinois.
Map of the Oregon Trail through Illinois.