After my self-testing, beginner-crushing, first 11 days, I spent a rainy Friday in Ashland doing some serious resting and preparing for my upcoming crossing of the Cascade Range.

While I couldn’t find a reliable answer on snowpack, the internet did tell me about four places along the route that would be likely to have water. At that point, I figured the crossing would be physically possible. So then I turned to my friends and family for tips on winter camping. After hearing their tips, it turns out that self-doubt was for naught, I really do know how to winter camp.

As Saturday morning dawned foggy, cold, and windy, I felt mostly ready to head off again. Still daunted by the continued unknowns, but steady enough to head out.

On this first Saturday back on the road I crossed two different worlds. First, from Ashland, I passed through the industrial parts of Medford. Second, turning north along the Rogue River, I was surrounded by spectacular views. The natural beauty of the river provided a peaceful contrast to the bustle of Saturday morning shipping and shopping in Medford.

Enduring yet more flat tires, I finally stopped for the night on forest service land. I set up my tent in a place surrounded by lodgepole pines, comforted by the sound of running water, and blessed by no snow. Knowing that the wee hours of the morning would be cold, I put on long underwear, socks, and a hat before crawling into my sleeping bag.

I was comfortable all night, so in the morning I was surprised to wake up to a little frost on my tent. It would have been lovely to snooze in the warmth all morning, but I forced myself up and out of camp. Many miles to go before I sleep!

Starting out wearing every layer I brought for riding (5 on top, 3 on bottom), my body was fairly warm. My toes, though, were a different (frostbitten) story. Only 15 minutes into the day’s ride, I had to find a sunny spot by the road to warm my feet (and my bike shoes) before really heading off for the day.

This day of riding was tough. The grade wasn’t steep and the scenery was gorgeous, but I struggled to find the rhythm of the road. Many hours and a couple summits later (at 5400 and 6000 feet), I was rewarded with a 13 mile downhill.

Even though this downhill came with a headwind, it was nice to be closing in on the end of the day. When I finally made it far enough to be within a day’s ride of Bend, I made camp in the high desert off another forest service road. Long before the sun set, I was curled up in my tent, clothed again in long underwear, and ready for bed.

The night was cold. Very cold. By morning I had put on all my extra layers and was marginally comfortable. Although the forecast had predicted a low of 32, the report that morning told me the temperature had dipped to 22 by first light.

Having learned from the previous day, I gave the sun some extra time to warm up the earth (and my bike shoes) before heading off. The ride north was flat to trending downhill, but a headwind, smoke from controlled burns, and tons of trucking traffic made this another slog.

By late afternoon, though, I finally made it to Bend. Which, it turns out, is a really beautiful place. Situated on the Deschutes River, Bend is a bike-loving oasis in the high desert. Moreover, the whole city offers amazing views of snow capped mountains in the Cascades.

Despite the daunting unknowns and the sloggy days of riding, I’m happy to have made the crossing. Now I know I can do more than I thought.