May 8, June 12, etc.
Midnight Mystery Ride
Second Friday of every month. midnightmysteryride.wordpress.com.
The Midnight Mystery Ride enjoys its mystique—but here's the bare minimum of what you need to know. Check the website on the day of the event for the ride's starting location (usually a bar). Get there, hang out, then succumb to wherever the night's ride may take you, no questions asked.
Various locations. Check shift2bikes.org for a full calendar.
Three weeks of "bikey fun," Pedalpalooza is essentially Portland's citywide, bike-themed summer camp. With dozens and dozens of biking events crammed into the span of less than a month, there's something for everyone. Lawyers? Jump in the lawyer ride. Pregnant? Try Pregopalooza. Fans of David Bowie and definitely not Prince—perhaps vice versa? The Bowie vs. Prince ride is for you. Nearly all events are free, so you have nothing to lose. Dignity is not a thing here.
Portland World Naked Bike Ride
Check pdxwnbr.org for details.
The Portland World Naked Bike Ride is a naked bike ride in Portland. It is not the only naked bike ride, but it is the only one with that name.
University of Portland, 5000 N Willamette Blvd., portlandcentury.com. 6 am. $79-$165.
One hundred miles is a Saturday ride for some Portlanders and a daunting feat for the less velo-versed, but Portland Century tries to bridge the gap with a flat, if long, course that's just as focused on sightseeing local landmarks as riding. The starting point recently switched from downtown's Portland State University to the University of Portland up on the bluff, where breakfast starts bright and early at 5:30 and the finish line is a Hopworks beer garden. After a lot of whining that the route was mainly in Washington, planners set a decidedly southern course for this summer.
Providence Bridge Pedal
Southwest Naito Parkway at Salmon Street, blog.bridgepedal.com. 6:45 am. $15-$60.
Rivaling the lawyer ride as one of Portland's longest-standing, Bridge Pedal sends spandex-clad hordes back and forth on seven-, nine- or 11-bridge routes (14, 25 and 35 miles, respectively). With the new Tilikum Crossing, it's 11 bridges for the first time. Registration grants you entrance to the Bite of Oregon, but don't have too much fun; you can't stop to take photos and you can't bring your dog.
Beaverton Banks and Beyond Tour
Papa's Pizza Parlor, 15700 NW Blueridge Drive, Beaverton. 6:30 am-4 pm. $35.
This Beaverton charity ride offers family-friendly route options from 32 to 100 miles, all starting from Beaverton's Papa's Pizza and touring through North Plains countryside to Banks. If you finish by 4:30 pm, there might still be a slice of Papa's pizza at the finish line. Proceeds fund the Northwest Bicycle Safety Council's community helmet program. Helmets required.
Bike Commute Challenge
Citywide during September. Free. Register online at bikecommutechallenge.com.
The month of September pits workplaces against one another in a citywide battle of bike commuters, according to an algorithm we don't really understand. "Team" is a loose term here, as individuals can register and often take top spots with 100 percent biking achievements.
Handmade Bike & Beer Festival
Hopworks Urban Brewery, 2944 SE Powell Blvd., hopworksbeer.com.
A merger of Biketobeerfest and the Oregon Handmade Bicycle Show, it's exactly what you'd expect: lots of beers and lots of terribly expensive and beautiful custom bikes from local makers. Oh, and also bike breakdancing, a bike-throwing competition and an adult tricycle obstacle course.
Worst Day of the Year Ride
worstdayride.com. $29 advance, $45 day of event.
Despite the ride's name, it was a beautiful day for the recent one. Anyway, how bad could it be with Santa cyclists, bumblebee cyclists, and bikers with flowers on their helmets and tiny dogs stuffed in their jackets? You also get coffee and doughnuts in the morning, lunch in the afternoon, and the pride that comes with saying you rode through the worst day of the year. They break the event into two rides: a 15-mile flat route in downtown Portland and a 46-mile course through the westside.
The Nieuw Ronde PDX ride starts in the Northwest Industrial District (Saturday); the La Doyenne of the East ride starts at the Springwater Corridor and I-205 bike path (Sunday). rondepdx.com. Free.
Inspired by a Belgian ride that's infamous for its near-impossible inclines, the De Ronde Van West Portlandia challenges riders of all ages to tackle 50 miles of the West Hills' steepest serpentine roadways. Still, 1,000 riders showed up for this year's race. It's unsanctioned and announced via social media and word of mouth (routes at ridewithgps.com). It got so popular that the founders added La Doyenne, a Southeast ride, the following day.
A Week of Bicycles
Portland Bike Polo
Alberta Park, Northeast Killingsworth Street and 22nd Avenue, portlandbikepolo.com. 3 pm-dusk Sundays.
Show up with your bike and a helmet and get ready to play urban Portland's closest bike cousin to the extravagantly great and ridiculous horsey-mallet sport that felled the great Carlos Gracida last year, except that in mood it's more Sunday softball.
Southwest 13th Avenue and West Burnside Street, zoobomb.net. 8:30 pm Sundays.
The smaller the wheels, the greater the glory. For 13 years, riders of all bikes and sizes have met at the Pyle, a piece of public art that anchors a stack of small mountain bikes in the West End, for an adrenaline-pumping nighttime ride down the West Hills.
PIR Monday and Tuesday Night Races
On summer nights, the two-mile raceway turns into a flat-circuit road race as official as they come in Portland, riding until the sunlight fails in search of the coveted monthly Castelli leader's jersey. An Oregon Bicycle Racing Association license is required.
Women and Trans Wrench Night
Bike Farm, 1810 NE 1st Ave., 971-533-7428, bikefarm.org. 4:30-7:30 pm every first and third Tuesday. Free.
Twice a month, the all-volunteer Bike Farm shop closes to cisgender men and hosts a special night for women and transgender riders to use its free expertise and tools.
Portland by Cycle Summer Rides
On alternating Tuesdays and Wednesday evenings in the summer, the Portland Bureau of Transportation offers free family-friendly bike tours of the city—sometimes to sweet shops, sometimes down greenways. Because the kids! But seriously, there's an amazing amount of free bike programs and classes.
Portland Lawyer Ride
Pioneer Courthouse Square, Southwest Broadway and Yamhill Street, 228-5222. Noon-1:30 pm Mondays and Thursdays. Free.
This group rides with widely varied participants, from Portland State undergraduates to retired lawyers. They do laps around the Southwest Fairmont Boulevard loop on Mondays, and venture into the West Hills up to Skyline Boulevard on Thursdays, in any weather. There's a no-rider-left-behind policy, but the air of friendly competition keeps rides at a brisk clip.
Fast Twitch Fridays
Alpenrose Velodrome, 6149 SW Shattuck Road, 227-4439. 6:30 pm Fridays, May-August. $10.
Fridays are all about speed at the Velodrome, a historic course opened as a dirt track in the early '60s. Race options include sprints, omniums (multiday races) and keirins (where the racers follow a pacer until the final breakaway lap). With track banks at almost twice the grade of regular circuits, the Velodrome isn't the place to break in your training wheels. An Oregon Bicycle Racing Association license is required.
Portland Velo Saturday Rides
portlandvelo.net. 9 am Saturdays.
It costs $30 for an annual membership, but for that you ride in a hell of a pack—the Portland Velo Cycling Club claims it's the largest regular ride in the area. Ride distances vary from 35 to 50 miles, planned by benevolent bicycle godparents who swear they won't leave you behind going uphill.