"This is the perfect way to move on from a bad year, from a bad experience," said Kathryn Bonn, of New York City, who shredded a printout of her boyfriend's e-mail breaking up with her.
The event, the second annual "Good Riddance Day," was sponsored by the Times Square Alliance, organizers of the New Year's Eve ball-dropping celebration.
Some participants wrote "the stock market" or "cancer" on a piece of paper and shredded it, while others shredded bags of bank statements and check stubs.
Kate Anello, a Yankees fan from New York City, destroyed a poster of the city's longtime rival, the Boston Red Sox.
"I hate them," she said. "It felt good."
City resident Jay Ballesteros won a $250 prize for the most creative object to be shredded: a sock representing all the socks that emerge from the laundry without their mates.
"I'm hoping to use the prize to buy some brand new socks," he said.