Winter break 🇺🇸

Posted on May 8, 2025

The week of riding between Klamath Falls and Portland ended up being a challenging one that put some big questions top of mind. After a few days with the Heaton family I hit the road again planning to follow a backcountry route through the Cascades; a few cold rainy days put and end to that idea.

Back when I left San Francisco, I had decided to continue northwards, keeping my original goal of riding to Alaska instead of opting to ride to the east coast and finishing my trip in Virginia. I had switched out sleeping bags and packed some warmer clothes thinking that ought to be enough. I’d heard mixed stories of Alaska in the winter time; some said “no problem,” others said “no way!” I figured I’d just go see for myself.

Leaving Klamath Falls

And into the mountains

Riding into Crater Lake National Park

A good campsite the night before a bad day

The first day out of Klamath Falls I camped short of Crater Lake National Park, opting instead to camp for free in the National Forest. The campsites in the National Parks can be quite expensive because they charge the same price whether you’re one guy on a bicycle or ten people in two cars. Some places have special “hiker biker” sites for those travelling without a car, but those have been few and far between. I packed a beer on my way out of Klamath Falls and enjoyed a nice camping spot along Annie creek all to myself.

Snow starting as I make my way up

The descent from Crater Lake

Chilly trees

The snow turning into rain

The next morning, shortly after starting up again, it started snowing. It was light at first but got heavier and heavier the higher I went. I took a break under the roof at the entrance toll booth to the park; there was no one there. It was a heavy, wet snow by then, which made it tough to stay dry. Eventually, after a few hours of slow climbing, I made it to the visitor’s center that I was happy to find open. I was invited inside to watch the short Crater Lake documentary film, which I rewatched several times as I warmed up in the theater. Once sufficiently reheated, I brainstormed together with park rangers Bonnie, Ayden, and Kate about my new best route to Portland.

Spending a few hours at Beckie's Restaurant

Dry, warm, and ready to ride

Wet conditions

There were three major routes I could’ve taken north from here. The coast, with it’s strong northerly winds, was already off the table way back in California. The east side of the Cascades was now proving to be too snowy on account of being too high. We quickly came to the conclusion that the best alternative was to descend to interstate 5 and to ride the parallel auxiliary roads. I abandoned the plan to stay up high riding dirt roads in the mountains and didn’t feel all too upset about it. Boom, decision made, let’s bundle up and descend to warmer climes.

Nice skies

Carrying on past sunset over Lost Creek Lake

Up and over into the Umpqua National Forest

The snow from up high quickly turned to a cold rain. Pretty miserable right about now. Without fenders on the bike there was plenty of water spraying up from the road, so my pants and shoes were properly soaked. I put on some dry socks, put my feet in plastic bags, and put my shoes back on. Looking pretty glamorous, I happened upon Beckie’s restaurant where I manned a booth for a few hours. Bottomless coffee, shepherd’s pie, blueberry pie à la mode, let’s go! After a few hours warming up in the restaurant the rain had subsided and I hopped back on the bike. It wasn’t the best of days as the dreary, dark weather can make it feel like the world is closing in on you. In the town of Prospect I chatted with Shane, a man working at a gas station, who spoke excellent Dutch. Small world. I rode on a bit further past sunset to a nearly empty campground. I was exhausted and it had been a pretty bad day. For the first time on my trip I slept terribly. Maybe it was all of the coffee?

Lunch break and drying my sleeping gear out

A nice, quiet road

And a good moment

Closed logging roads

A cool covered bridge in Douglas County

Nowhere special

Cool mailbox

I made it down to Shady Cove the next morning, stocked up on some food, used the WiFi at the library, and then turned north again. What followed were two nice days riding toward the I-5 corridor through the Umpqua National Forest and seeing some logging areas in operation. Those two days were actually really nice. I had managed to avoid more rain, the sky was dynamic with lifting fog and cool clouds, the roads were quiet, and there were plenty of friendly folks out and about. I rode past the very Wes Anderson looking Ranch Motel in Rice Hill and stopped to learn more. Owners Tim and Lisa were excited about my enthusiasm and gave me a tour and fed me lunch. Once along the I-5, though, the road became quite busy until I made it to Eugene.

Foggy hill

On the logging cut-trough

And back on the road

And off the road again

A logging depot

With some cool machines

One of the nicest tool stores I've ever visited!

Bad cycling roads

The Ranch Motel in Rice Hill, Oregon

No tent campers allowed at this roadside spot

The Umpqua River

In Eugene I stayed a few nights with John and Lisa and then with Tomoko. The weather forecast for the Willamette valley was looking bad but I had to carry on. I stayed with Warmshowers hosts all the way to Portland. As much as I had previously wanted to see this quite well known wine region, now I just wanted to stay dry and get to Portland. It was consistent rain and it wasn’t letting up. I figured this was that Pacific Northwest weather everyone was always talking about.

Truck

Fire hydrant

The Willamette Valley scenic bikeway

John was curious what my bike weighed

Mushrooms popping out of Tomoko's garden

Sy's pizza in Eugene

Halloween cop car

Nice countryside

A quiet little stretch leaving Eugene

Yeehaw

A nice little roadside spot where I got to speak some Spanish again

Picking up some screws

In Portland I stayed with Lisa for a week as I decided what my next move would be. I’d found the road through northern California and Oregon quite tough and the weather wasn’t helping one bit. For now, the cycling had been uncomfortable and not at all fun but going further north, later in the year could also be dangerous. I roamed around Portland for a few days, read books, ate pizza, and called with family and friends to help me make a decision.

Riding into Portland

A very nice Pedestrian/cyclist/light-rail bridge

The Steel Bridge in Portland

Eating pizza and before Powell's Books! An incredible used bookstore in Portland

I found Klaas and Michelle who were willing and able to store my bike for the winter and I also found a cheap flight home. It ended up being a pretty easy decision once I let go of any self-imposed demands to keep my trip continuous, whatever that means, and just keyed in on what I really wanted to do right now. I stored my bike, said “see ya later,” and got on the plane.

A fun street mural

Sunset over Portland

The Steel Bridge again

A nice sign in downtown Portland

Another cool sign in outer Portland

Now about five months later I’m back in Portland and honestly quite excited for these last few months of riding. I think it will be a really beautiful part of the trip with some of the most remote and rugged landscapes I’ve yet come across. I’m glad I took the time to wait and to allow myself to recharge; the only fear I have now is whether or not I can pick the trip up again where I left off. Only one way to find out!