Midnight Mystery Ride

Calling all night owls: this ride follows a different route, known only to the ride leader, departing at midnight every second Friday of the month, year-round. Start location, usually a dive bar, is announced day of. Often ends with a bonfire. Can get wild. 

Our Mother the Mountain

Prefer to stay away from pavement? Our Mother the Mountain goes for gravel, forest roads, and singletrack, with occasional bonus bushwhacking. Bring strong quads—these can be drop rides, meaning the group won’t wait for slower cyclists—and solid navigation skills. 

Black Girls Do Bike

This national org aims to get more women of color on bikes. Local chapter leader Keyonda McQuarters helps organize two all-levels-welcome rides per week, and the Facebook group, which counts about 300 members, is a one-stop resource for cyclists seeking advice. 

Biking About Architecture

A leisurely paced tour the final Saturday of every month of hidden architectural wonders and oddities: think historic mansions in Alameda, cohousing in Cully, and bike windmills and dome homes in Woodstock. Ends with drinks and eats at a nearby pub.

Portland Bicycling Club

Formerly the Wheelmen Touring Club, this 48-year-old nonprofit organizes loads of group rides—up to two dozen each week—across the metro area, rated by terrain (some super-flat, others mega-hilly) and pace. Plus:numerous offerings for new riders. 

Portland Bike Polo

Bike polo swaps horses for two-wheeled steeds: riders pedal around with mallets as they attempt to whack a small rubber ball into a goal. Not your speed? Also a primo spectator sport. 

Urban Adventure League

A motley assortment of themed and educational rides—topics might include history, ill-fated freeway projects, or pizza—at a casual pace, plus occasional weekend-long bike camping trips.

Thursday Night Ride

A weekly tradition since spring 2015. Every Thursday at 7 p.m., riders gather at Salmon Street Springs fountain for a mass ride. Decidedly social pace, with a different route each week. 

WTF Bikexplorers

A locally founded community for women and trans, femme, nonbinary, and genderqueer riders who like to explore and travel by bike. Its second annual summit (four days of rides, clinics, campfires, and more) is August 15–18 in Vernonia.

PDX Coffee Outside

Not strictly a bike gathering, but a meetup of bikey folks who gather every Friday at 7 a.m. at a different park in Portland with camp stoves, coffee beans, and doughnuts. Bring your own mug.