The Worst Day of the Year Ride is the annual cycling event held in Portland, Oregon, in the United States.

Race organizers started a costume contest and the event has been called a "winter Halloween for cyclists".

[11] In 2010, the ride was held on Valentine's Day[7] and attracted 3,500 participants, making it the second most popular bike event behind Bridge Pedal, which attracts more than 20,000 attendees (this does not include the city's World Naked Bike Ride, which is not officially sanctioned).

[10] Despite the event's name, according to organizers it "never really rained" for the first thirteen years the race was held.

[4] In 2014, the more challenging 45-mile route was canceled "for safety reasons" due to bad weather.