The Oregon Trail


If you have the time, Hwy-2 follows a lovely route from Rockford along the Rock River southwest to the quaint old town of Dixon, where the Ronald Reagan Boyhood Home (816 S. Hennepin Ave., 815/288-5176, daily May-Oct., $8) preserves the house where in the early 1920s the late “Great Communicator” (1911-2004) spent his preteen years.

Midway between Rockford and Dixon, in Lowden State Park, a rather majestic Eternal Indian statue inspired by the great chief Black Hawk stands high above the river outside the town of Oregon.


Between Rockford and Chicago, US-20 is a slow, winding, and poorly signposted alternative to the high-speed I-90/Jane Addams Memorial Tollway. It’s a leisurely route, with few identifiable attractions except for the road itself, which cruises through small towns surrounded by farmlands and lined by fruit-and-vegetable stands. The one real draw here is a mile (1.6 km) east of the tiny town of Union (pop. 561), where the sprawling Illinois Railway Museum (815/923-4391, daily, $11-15) displays the country’s widest range of track-based transportation: streetcars, interurban trolleys, and railroad cars, with historic engines running weekends throughout the year.

Oak Park

Running parallel to and south of the I-90 Northwest Tollway, old US-20 approaches Chicago from the northwest past Schaumberg and O’Hare Airport before bending south near Oak Park (pop. 52,265), Chicago’s most interesting suburb. Just 10 mi (16.1 km) west of the Loop, easily reachable at the end of the Lake-Dan Ryan CTA “L” line, this sleepy but well-heeled neighborhood was the boyhood home of Ernest Hemingway, and before that Oak Park was the home and proving ground of America’s best-known architect, Frank Lloyd Wright. Visit the Frank Lloyd Wright Home and Studio (951 Chicago Ave., 312/994-4000, daily, $18 and up) for a fascinating look into the life and work of the great architect. Take a guided tour of the house he designed, remodeling almost constantly between 1889 and 1909 as his practice, and his family, grew. He also completed many other buildings in this turn-of-the-20th-century suburb, including the austere classic Unity Temple.

Oak Park has good transit connections to Chicago and makes a pretty good alternative base, thanks to the Harvey House Bed & Breakfast (107 S. Scoville Ave., 708/848-6810, $195 and up), which is no relation to the famous 1920s railroad hotels but offers comfortable rooms within walking distance of Frank Lloyd Wright’s Unity Temple and the Oak Park CTA “L” station.

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

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