Galena & Northern Illinois
The highlight of this region is the hilly northwest, where cottonwood trees, grazing horses and scenic byways fill the pocket around Galena. En route is Union, where the Illinois Railway Museum sends trainspotters into fits of ecstasy with 200 acres of locomotives.
While it sometimes gets chided as a place for the 'newly wed and nearly dead,' thanks to all the tourist-oriented B&Bs, fudge and antique shops, there's no denying little Galena's beauty. It spreads across wooded hillsides near the Mississippi River, amid rolling, barn-dotted farmland.
South of Galena along a pretty stretch of the Great River Road is scenic Mississippi Palisades State Park, a popular rock-climbing, hiking and camping area; pick up trail maps at the north entrance park office. Further downstream, the Quad Cities – Moline and Rock Island in Illinois, and Davenport and Bettendorf across the river in Iowa – make a surprisingly good stop.
Located 10 miles west of the Loop and easily reached via CTA train, Oak Park has two famous sons: novelist Ernest Hemingway was born here, and architect Frank Lloyd Wright lived and worked here from 1889 to 1909. During Wright's 20 years in Oak Park, he designed many houses. Stop at the visitor center and buy an architectural site map ($4.25), which gives their locations.
A surprise awaits near Collinsville, 8 miles east of East St Louis: classified as a Unesco World Heritage site with the likes of Stonehenge, the Acropolis and the Egyptian pyramids is Cahokia Mounds State Historic Site. Cahokia protects the remnants of North America's largest prehistoric city (20,000 people, with suburbs), dating from AD 1200.
Evanston & North Shore
Evanston, 14 miles north of the Loop and reached via the CTA Purple Line, combines sprawling old houses with a compact downtown. It's home to Northwestern University. Beyond are Chicago's northern lakeshore suburbs, which became popular with the wealthy in the late 19th century.