In light of the COVID-19 pandemic, we advise that you check local guidelines before making plans. If you choose to travel, please do so safely and responsibly.

The Oregon Trail

Freeport

Midway between Galena and Rockford, the oddly named town of Freeport (pop. 23,920) is neither a port nor even near any body of water. According to the WPA Guide to Illinois, the name was bestowed by Elizabeth Baker, the wife of the community’s founder, William “Tutty” Baker, to satirize his fondness for providing free river ferry passage and even free room and board to passersby.

There’s no free lunch here today, but Freeport does offer at least one good reason to stop: The Ice Cream Parlor at the Union Dairy (126 E. Douglas St., 815/232-7099), two blocks north of the US-20 Business Loop, has been serving ice cream since 1914.

In the small park next door, an oddly distorted statue marks the site of the second Lincoln-Douglas debate, held here on August 27, 1858. A plaque quotes both men equally, with Lincoln’s “This government cannot endure permanently half-slave and half-free” opposing Douglas saying, “I am not for the dissolution of the Union under any circumstance.”

Rockford

Spreading haphazardly along the leafy banks of the Rock River, Rockford (pop. 146,526) is a big, somewhat sprawling postindustrial city 5 mi (8 km) west of the busy I-90 toll road from Chicago. US-20 bypasses the down-at-heel downtown area that, if the denizens wore more hats, would look like a film set on Main Street of industrial America circa 1949. Unfortunately, many of the classy office buildings and storefronts here have been abandoned in favor of anonymous office parks and shopping malls closer to the I-90 corridor.

North of downtown, along the west bank of the river and away from the frantic highways, one great place to check out (especially if you have creature-loving youngsters with you!) is the Burpee Museum of Natural History (737 N. Main St., 815/965-3433, daily, $10), where an entire floor of paleontology exhibits is highlighted by the skeleton of a 21-ft-tall (6.4-m), 65-million-year-old T. rex called “Jane.” Further north along the riverside, if the weather is nice, take time to stretch your legs while exploring the manicured grounds of Anderson Japanese Gardens (318 Spring St., 815/229-9390, daily, $11).

After exploring Rockford’s nooks and crannies, taste your way through the tapas at Abreo (515 E. State St., 815/968-9463). For something hoppy, malty, and liquid, try the Carlyle Brewing pub (215 E. State St., 815/963-2739).

Rockford has lots of places to stay, from all the main chains along the interstate to the Alpine Inn (4404 E. State St., 815/399-1890, $50 and up).

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

Related Travel Guides