Chicago
Route: Hyde Park loop
Distance: 5 miles (8 km)
Move over, Grant Park; there's a new bike ride in town: the South Side neighborhood of Hyde Park. Although it's probably best known as President Obama's old stomping grounds, it has several other oft-overlooked city treasures. Start at the DuSable Museum of African American History in Washington Park, Hyde Park's western border, and head northeast through the neighborhood's quiet, leafy streets. Cycle up to President Obama's home (5046 South Greenwood Avenue), then wend your way back down to Frank Lloyd Wright's Robie House (5757 South Woodlawn Avenue), which is the greatest example of the architect's Prairie style. A few blocks to the east is Jackson Park, which contains the excellent, kid-friendly Museum of Science and Industry and the quiet oasis of the Osaka Japanese Garden. Don't miss the University of Chicago campus on the neighborhood's southern edge; there are two museums here, the Smart Museum of Art, a lovely small gallery with an impressive collection, and the Oriental Institute Museum, which has a significant collection of ancient Near East artifacts.
You can rent a bike for $8 per hour at Bike and Roll in Grant Park downtown (or check out the Chicago Bike Shop Database for a good list of area bike shops), and either take a trolley or ride the 9 miles (14.5 km) south to the DuSable. After your tour, you'll find no shortage of places to recharge in Hyde Park: Valois, on East 53rd Street and South Lake Park Avenue, is a popular cafeteria that serves a great breakfast and all-day comfort food.