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The most popular cycling event in my area is the annual Starlight Spectacular (last year was the 25th anniversary) which is a big nighttime ride held during the summer to raise funds for the local trails and open space group. It's really fun, there's food at the start and the finish, and the mass start is amazing since there are thousands of people there on bikes, some with fancy light displays or even pulling floats. Lots of people bring their kids and just cruise the short distance loop, but there's no rule that says you can't race around the course that goes through the downtown area and then back into a big park which is full of rolling hills and tight turns that are fun to ride during the daytime, but really exciting to ride at night since there are almost no streetlights in that section.