It’s a terrible day in the neighborhood

With Valentine’s Day approaching, some single Portlanders might be planning to hide indoors and drink cheap wine on what they consider to be the worst day of the year. The folks partaking in the ninth-annual Worst Day of the Year Ride will be having plenty of fun outside though—and it has nothing to do with Valentine’s Day.

Up to 3,500 cyclists are expected to participate in this year’s Worst Day of the Year Ride, which starts in downtown Portland. In addition to a local crowd, participants are streaming in from out of state, from places like Idaho, Michigan and even parts of Canada.

When it started nine years ago, the ride boasted a sizeable 250 riders. It’s since come a long way in drawing folks from all over the country.

“People are embracing this ride as their annual tradition,” said Ayleen Crotty, the event’s coordinator and marketing director. “People know Portland is a bike-friendly city.”

The ride is organized by Good Sport Promotion, which runs other popular events like the Night Ride and Biketoberfest.

Proceeds from the ride will benefit programs at the Community Cycling Center, as they have since the annual event’s inception. These programs range from handing out free bike lights, to providing low-income families with bikes and helmets. CCC focuses on enhancing community and creating equal opportunity for people to have bikes.

They also offer low-cost bicycle maintenance classes and cheap parts at their shop in northeast Portland.

Aside from benefitting a good cause, the Worst Day of the Year Ride is just plain fun. Thousands of cyclists show up—more every year—and about half of them are in costume, many of whom have obviously put tons of work into their attire.

“About a quarter of the riders really go all out on their costumes,” Crotty said. “They’ll put wigs on their helmets.”

Costume judges will filter through the crowd throughout the event and announce winners of the costume contest at the end. This year they’re giving away free passes to the Night Ride in July.

The ride’s name has nothing to do with the holiday—this year it simply happens to fall on Valentine’s Day. The name was created based on historic data that reveals severe weather events throughout Oregon in the month of February. The Willamette River rose 31.8 feet during February 1996, during what’s commonly known as the Great Flood in Portland. Also in February—of 1933—the cities of Seneca and Ukiah dropped to the state’s all-time record low temperature of negative 54 degrees Fahrenheit.

The ride is sponsored by a number of Portland businesses. Sponsors will provide riders with free perks like coffee, cookies and soups at rest stops. Mechanical bicycle support will also be on hand.

To please both the casual cyclist and the more serious, pedal-pumping cyclist, there are two routes to choose from. An 18-mile route through downtown and nearby neighborhoods takes riders along a fairly flat course with three stops along the way. The Challenge Loop casts riders into the steep and curvy West Hills for a total route of 40 miles.

Space permitting, registration will still be open Saturday and at the pre-ride check in on Sunday. Spectators are welcome and can refer to the ride’s website.