Bike City, USA — aka Portland — isn’t content with the everyday cycling that makes ours the city with the highest percentage of bike commuters in the nation. Nope, bike-loving Portlanders have come up with all sorts of rides and events that fill the calendar with two-wheeled shenanigans.
Worst Day of the Year Ride – February
Die-hard riders will spend 12 months of the year behind handlebars, but anyone worth their chain stains makes it to the Worst Day of the Year Ride in mid-February. Timed to coincide with the year’s worst weather day, the 16-mile (26 km) fun ride (or 45-mile [72 km] challenge course) ends with cold beer and hot soup at Southeast Portland’s Lucky Labrador brewpub.
Filmed by Bike – April
In a city that loves movies almost as much as it loves bicycling, it’s only natural that there’s a festival celebrating both. Filmed by Bike is a two-day festival at the Clinton Street Theater, screening bike-themed independent short movies from around the world. In all, about 30 films, each less than eight minutes in length, celebrate every angle of bike culture.
Tweed Ride – April
The dream of the 1890s is alive during the Tweed Ride, an annual affair in which dozens of riders don their most dapper duds and take a spin on vintage bikes. Expect to see waxed mustaches, fancy hats and a few penny farthings; the after-party is customarily held at Velo Cult bike shop.
Sunday Parkways – May-September
Held in several different neighborhoods each year, the free Sunday Parkways rides convert city streets into car-free zones, encouraging cyclists to explore different parts of the city. Each event features stops in city parks along the route, with entertainment, food and activities.
Pedalpalooza – June
For three weeks every summer, bike geeks organize about 200 events to celebrate all that is cycling during Pedalpalooza. There’s a major menu of rides, performance art, races, taco stand tours, gay pride bike parades, bike polo and more, including the largest staging of the World Naked Bike Ride.
World Naked Bike Ride – June
The World Naked Bike Ride is a global event, with rides held in 74 cities from Amsterdam to Perth, but Portland lays claim to the world’s largest ride, drawing more than 8,000 cyclists clad in various combinations of swimsuits, underwear, body paint and smiles in 2013. And don’t worry, riding naked in Portland is legal; the event is considered a protest and, therefore, nudity is permitted under Oregon’s liberal free speech laws.
Gourmet Century – July
The Gourmet Century was created by Chris King, the founder of Portland-based Chris King Precision Components, and is a testament to the fact that Mr. King loves food just as much as he does bikes. The metric century sells out quickly, luring riders with the promise of fine roads and fine food.
Cirque du Cycling – August
Held on North Mississippi Avenue, the Cirque du Cycling festival incorporates live music and entertainment with a street race, a family ride and a beer garden; proceeds from the festival benefit a local charity.
Bridge Pedal – August
The Bridge Pedal is your one chance to pedal fancy- and car-free with nearly 20,000 other cyclists across Portland’s Willamette River bridges, from the Sellwood to the St. Johns and most others in between. The event’s route includes the top decks of the Marquam and Fremont bridges, normally open only to automobile traffic on interstates 5 and 84.
Portland Twilight Criterium – August
Every August, the Portland Twilight Criterium brings the nation’s fastest professional cyclists to race on city streets and compete for the area’s largest purse. The course encircles the Pearl District’s North Park Blocks, where more than 15,000 spectators are close enough to feel the wind from the peloton.
Zoobombers – Every Sunday
The recipe is insane but simple: The Zoobombers gather every Sunday evening at the corner of Southwest 13th Avenue and West Burnside Street, ride MAX light rail to the Washington Park station (Oregon Zoo stop) and bomb back down via the streets of Portland’s West Hills. Regulars prefer to ride small children’s bikes or their own customized contraptions. If you’d rather just get a taste of this particular slice of Portland culture, visit the People’s Bike Library of Portland sculpture at 13th and Burnside.