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It varies each year (scheduled outside of Indiana University home football game weekends....due to the availability of hotel/motel rooms in the area. To see the date and other information, see http://www.hillyhundred.org). This year the date is October 23-25. The actual ride days are the 24th and 25th (doing approximately 50 miles each day with a short cut on at least one of the days. The ride is a rolling celebration of cycling. They register up to 6000 people and another 2 thousand show up and ride without paying (I discourage this as the event will only continue to exist with the income from this ride. At each reststop (they are numerous) there is entertainment, food, and drink.
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