From Lake Shore Drive to the North Shore, from earliest morning to the middle of the night, from clothed to fully naked—in the summer, Chicago bike enthusiasts take their pick of roads, rides, and races.
Bike the Drive The city closes Lake Shore Drive to cars and opens it to bikes for this annual event benefiting the Active Transportation Alliance. A postride festival from 8 AM to noon features sponsor booths and live music, plus breakfast from Goose Island for $7. The ride begins at Columbus and Jackson. Sun 5/29, 5:30 AM start, entry to the drive stops at 9 AM, event ends at 9:45 AM, 312-427-3325, ext. 251, bikethedrive.org, $45-$55.
Udder Century The 29th annual Udder Century Ride offers routes of 32, 51, 61, 75, and 100 miles and a pasta dinner at the finish. Sun 6/5, registration and start from 6:30 to 10 AM, Donley's Wild West Town, 8512 S. Union Rd., Union, mchenrybicycleclub.org, $22-$30, $10 kids 6-12, free for kids under 6.
American Lung Association's Fight for Air Ride Participants can choose between a three-day ride starting Friday or a two-day ride starting Saturday; riders cover about 50 miles per day. Starts at McHenry County College, 8900 US Hwy. 14, Crystal Lake, and bikes to Lake Geneva. Fri-Sun 6/10-6/12, 312-781-1100, laketourbiketrek.org, $100 registration (includes lodging and meals), $600-$800 fund-raising minimum per rider.
Fork and the Road Tours of ten to 20 miles, ridden at a leisurely pace and organized around food themes. Upcoming themes include deli fare and Mediterranean and Asian cuisines; the first tour of the 2011 season, Sun 6/5 from 11 AM to 3:30 PM, highlights frozen desserts. Forkandtheroad.com, $50-$60.
World Naked Bike Ride Politically inspired riders meet at a location disclosed a few days before for a colorful, attire-limited ride through the streets of Chicago. Sat 6/11, 6-11 PM, chicagonakedride.org. F
Le Tour de Shore This benefit ride for Maywood Fine Arts starts in Chicago and goes to Michigan City, Indiana, the first day (66 miles) and Sawyer, Michigan, the second (32 miles). Fri-Sat 6/17-6/18, Millennium Park, Michigan and Randolph, 312-742-1169, letourdeshore.com, $60-$70, optional $24 bus ride back to Chicago.
Bicycle Illinois A ride across the state—500-600 miles—starts in Cairo, stops overnight in Carbondale, Centralia, Effingham, Champaign, and Kankakee, and ends in Chicago. Sat-Sat 7/9-7/16, 877-868-7455, bicycleillinois.com, $650, $125 for one day.
Ride for AIDS A two-day, 190-mile ride from Evanston to Elkhorn, Wisconsin, and back. Proceeds go to the Test Positive Aware Network. Sat-Sun 7/9-7/10, 773-989-9400, rideforaids.org, $85 registration fee (includes meals and lodging), $1,000 minimum fund-raising.
The L.A.T.E. Ride Thousands of cyclists participate in this 25-mile middle-of-the-night ride, which benefits Friends of the Parks. Live entertainment precedes the event Saturday night at Buckingham Fountain. Sun 7/10, 1 AM, Grant Park, Buckingham Fountain, Columbus and Congress, 312-857-2757, lateride.org, $40-$45.
Cowalunga At this fund-raiser for lung-disease awareness, choose a one-day (65 miles), two-day (130 miles), or three-day (190 miles) tour beginning in Gurnee Mills; the longest route ends in Hubertus, Wisconsin. Sat-Mon 8/6-8/8, Gurnee Mills Mall, 6170 Grand, Gurnee, 888-880-5864, cowalunga.com, $25-$185 registration, $50-$1,000 required fund-raising, optional bus ride home $25.
The Wright Ride This architectural tour focusing on the work of Oak Parker Frank Lloyd Wright has four distance options: 17, 30, 50, and 62 miles. Sun 8/21, 6:30 AM, oakparkcycleclub.org, $20, free for kids under 12.
Four-Star Bike Tour Three options for exploring Chicago by bike: the 12-mile Neighborhood Ramble, the 35-mile Boulevards & Beyond, and the 65-mile Ultimate Neighborhood Ride. All start and finish at the corner of Morgan and Taylor on the UIC campus; registration includes live entertainment at a postride festival. Sun 8/28, start times between 7 and 9:30 AM depending on route, 312-427-3325, ext. 225, fourstarbiketour.org, $30-$40, $15 kids under 18.
North Shore Century The Evanston Bicycle Club's annual event has route options ranging from 25 to 100 miles, with the longest route ending in Kenosha, Wisconsin. Riders can choose their own start time once registered; course closes at 6 PM. Sun 9/18, registration starts at 6 AM, Dawes Park, 1700 Sheridan, Evanston, 847-448-8260, evanstonbikeclub.org/nsc, $17-$25, $10 kids under 17.