Galena, Ill.

1. The street above Main Street
Yes, you’ve got to walk the walk and shop the shops on Main. But climb one street up (way up), and you’ll come to Bench Street–my favorite street in town (full disclosure: my grandmother and/or other relatives lived here for most of the 20th Century). No shops, but historic and architecturally fascinating buildings galore–and 4th floor entries to the back of many Main Street buildings.
2. The best view in town
Keep climbing on Galena’s famous stairs–or drive on a switchback road–to the top of the hill and the lookout from the old high school (now condos). Oddly enough, few people do.
3. The landmarks
Hate to drag you away from the shopping, but there are some historic sites you should visit. Grant’s Home (remarkably small), of course. But also the Old Market House, the Dowling House (oldest in town–1826) and the Washburne House, among others.

4. The Galena History Museum
Thomas Nast’s famous painting of Gen. Lee’s surrender to Gen. Grant, “Peace in Union,” is the star. But they’ve also got a Grant cigar butt. And it’s on Bench Street.
5. Greenwood Cemetery
West of downtown, it’s the final resting place of five of Galena’s nine Civil War generals, though not you-know-who (but there is a Grant family marker).
6. The roads out of town
This may be the most scenic area in Illinois, and it’s a shame if you don’t see more of it than just the views from beautiful but busy U.S. Highway 20. Blackjack Road and Stagecoach Trail are worth a trip on their own.
7. Chestnut Mountain
Who knew Illinois had such a dramatic place to ski–or see? A half hour from town, this resort sweeps down 475 feet to the Mississippi River bottom.