Photos by Misha Ashton moore

There's a lot to be said for biking in the rain. Sure, Portland's winter skies are gray and leaky and the sun falls behind the West Hills so, so fast. On the other hand, there's not much snow or ice to worry about. Much thinner herds clog the path along the west bank of the Willamette.

Winter cycling in Portland is a chance to prove yourself a serious cyclist and outsmart nature. It's possible to get by wearing yellow rubber kitchen gloves and lining your old leather-bottomed JanSport with a garbage bag. But, trust us, the right stuff really helps. We've scoured local bike shops and blogs for winter-ready clothing, bags and bikes that get us in the right gear for the impending wet months. Much of this was designed or made by Portland companies, who understand better than anyone what riding here in the winter is all about. The other items are just plain awesome. Try to have fun out there. 


Cascade Flyer

Kinn Bikes, $2,350.

You know those tow-hitch baby carriages that swing your below-line-of-sight child into opposite lanes of traffic as you talk on your cell phone while riding your bike? Well, stop that. It's really scary. Seriously. Anyway, aside from being a solid cargo bike that can fit on the front of a bus, designer Alistair Williamson's Portland-made bike is a wonky engineering-obsessed vision of a kid taxi, with a mega kickstand, a seat over the wheels, mini handlebars and a little bell in the back so the kid can communicate with you using (slightly muted) Morse code. The back is made to mesh up perfectly with an equally wonky Dutch child-seat called Yepp ($230). The Cascade Flyer ain't cheap at $2,350, but it also isn't the $5,000-7,000 you pay for other bikes made here in town. And it's way prettier than a station wagon. Their Kickstarter will net you $250 off the bike.

Sirrus Sport Disc

Specialized, $750 at 21st Avenue Bicycles.

Don't be lulled into false complacency by the Native American Summer (in Lithuania, they call it the "summer of old ladies.") At the end of October it's going to start raining, mostly gently but pretty much incessantly, for six endless months. So we asked our friendly local bike shop, 21st Avenue Bicycles, to put together an affordable version of the ultimate rain bike, to get you through the nearly half-year of dark mornings, dark afternoons and dark evenings. The Sirrus from Specialized has hydraulic disc brakes for low maintenance and predictable braking—seriously, they're the same type of brakes used on motorcycles and passenger cars. To avoid that constant spidering spray of dirty water dampening you from underneath (in the bad way), they've installed a longboard fender set from SKS ($50). For shopping trips, there's a market rack from Civia ($70) outfitted with a locally made North St. pannier (see below). Your dry butt, skin-intact knees and dry root vegetables from the local all-weather farm stand will thank you.


Club Pro jacket

Showers Pass,

This jacket ($110) should be No. 1 on your winter wish list. It's waterproof, with well-positioned pit zips and vents that keep you from getting clammy, and it's roomy enough that you can wear a cozy sweater underneath on those unusually frigid days. It comes in powder blue as well, but you're less likely to be sideswiped on Barbur while wearing neon yellow.

Knitted winter hat

 Rapha, Available at River City Bicycles.

This Belgian-style hat ($55) from Rapha—a London-based company that has its U.S. headquarters in Portland—is about as luxurious as it gets. The super-soft outer layer is 100 percent merino wool, the fold-up earband has a pretty purple stripe and the brim is big enough to stop the fattest raindrops. 

Reversible rain hat

Gobha Clothing,

The husband-wife team at Gobha make these hats ($55) in San Francisco, but they seem custom made for Portland winters (and not just because they're emblazoned with a bird on the back). One side boasts a tightly woven softshell that's windproof and water repellent, while the other has snazzily striped, cozy New Zealand merino wool. The earflap helps keep you warm, too.

Rain chaps

Rainlegs,, Available at Clever Cycles.

It's more often drizzling than dumping in Portland, which means a full pair of rain pants can be overkill. That's where these Netherlands-designed rain chaps ($44) come in handy. Compact and waterproof, they'll protect your upper thighs, which get the greatest hammering on a rainy ride. And there's no awkward tugging over bulky shoes—once you arrive, just unbuckle and stride on in, cowgirl.

Express Long Sleeve Half Zip

Icebreaker, 1109 W Burnside, 

It's tough to beat wool for fast-wicking warmth, and this midweight baselayer ($119.99) from Icebreaker, which has its design headquarters in Portland, keeps you toasty without creating bulk. "Doesn't stink," boasts the packaging, which means you can head to the bar after your commute without sending your friends fleeing.

Luminite gloves

Endura, Available at Bike Gallery, Universal Cycles, Bike N Hike and many other retailers. 

Waterproof membrane? Gel padding? High-visibility accents? Terry-cloth panel on the index finger designed for wiping away sweat, tears, blood or rain? Check, check, check and check. With a soft lining and perfectly placed stretchy panels, these gloves will keep you warm and dry in the grossest conditions.


Legno helmet

Coyle Designs,

Corvallis' Dan Coyle has been experimenting with wooden helmets since the 1990s before going commercial in 2010. His line of helmets isn't cheap—this model is $405—but it's very stylish, with a hardwood shell and honeycomb lining of natural cork proven crash-safe through laboratory testing.

Crosspoint hardshell glove

Showers Pass,

This merino-lined hardshell glove from Portland's Showers Pass ($95) is much warmer and drier than thin softshell gloves and nearly as breathable. The best feature of these mitts? Perfectly articulated fingers, which curl nicely around your handlebars. It's a serious glove—you'd be comfortable skiing in it.

Zoobomb jersey

 Portland/Oregon Cyclewear,

Icebreaker briefly made very nice wool cycling jerseys, but no more. This Portland company has been custom-making them for almost a decade. The long sleeve version ($85) is a supple, sweater-y shirt with a zippered pouch. You can ride all day in it and still feel at home in a coffee shop or bar.

Softshell trouser

Swrve, Available at 21st Avenue Bicycles and Joe Bike.

Swrve's softshell pants ($150) come from sunny Los Angeles but are perfect for Portland thanks to their casual jeans-style pockets, soft fleece lining and water-repellent shell. Maybe that's because Swrve GM Muriel Bartol was a Reedie, and knows what we need up here.

Last Belt
Blaq Designs, 1100 SE Division St., 

Portland's Blaq Designs makes a large range of bike accessories, including panniers, messenger bags and pouches. The $72 Last Belt is made with ultra tough seatbelt webbing that should last, well, forever.

Shoe covers

Neon Frontier, Available at the
City Bikes annex. 

Waxed cotton jackets kept the cowboys dry in frontier days. Now, these covers ($45) from local craftsman Ben Houston use the material to keep your Pumas dry while biking to the record store. Plenty of covers fit over riding shoes, but these work well with normal shoes. 


CloudCover iPhone 5 case

Showers Pass,

Camper Satchel

Sketchbook, Available at Clever Cycles.

Eugene's Amber Jensen makes this gorgeous yet rugged waterproof backpack ($249). Made of heavy-duty waxed canvas, the rolltop design means you can carry a little or a lot. It reminds us of something the Von Trapp children would carry through the Alps, but it'll also keep your laptop dry as you pedal across town.

Aether Demon and Spaceship 3 lights

Portland Design Works, 

Woodward Convertible

North St., 2716 SE 23rd Ave., 

It's a backpack! It's a pannier! It's a backkier! This $250 combo bag from Portland's North St. is waterproof, neither too big nor too small and has a side pocket for your lock, lamps and keys. Its ability to pop off the rack and onto your back for a hike around town is the best trait, though.