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Though it typically takes place in May, this year's car-free ride on the recently-renamed Jean Baptiste Point DuSable Lake Shore Drive is moving to September. Riding on a 30-mile course that stretches from Bryn Mawr Ave on the city's North Side or the Museum of Science and Industry on the South Side, cyclists can take a spin on the popular lakefront thoroughfare while it's completely closed to cars for 4.5 hours.
You'll have to wake up early (the course opens at 5:30am) and enter from one of five designated entry points along the road. But the novelty of biking on a stretch of pavement that is decidedly not bike-friendly is worth the hassle. Plus, proceeds from the event support the Active Transportation Alliance, a nonprofit organization that working to improve conditions for pedestrians and cyclists throughout Chicago.