A person holds up a sketch of a bicycle in nature
A person holds up a sketch of a bicycle in nature

When I was 14, I made a goal of riding what I like to call, a Thousand-Mile Summer. My Dad thought the idea was brilliant, and wanting to help me achieve this, we went into a local bike shop together to get road tires for my mountain bike. This idea made the workers at the store chuckle when I explained why I needed road tires. I was slightly embarrassed, which made me want to do it even more, to prove them wrong of my silliness. I set out on my first ride of 30 miles along the Bay Road in my hometown of Newport and back to my house in Nye Beach. I did this over and over for months, logging my mountain biking trails and road trails, and eventually, I hit 1,000 miles.

Looking back, I can see how ridiculous my goal was, but I never stopped creating these little adventures. Much like my teenage self, I continued my ideas of things I could do with the power of my body.


Kelsea, right, and team with all the gear they need to bike, hike, and ski their way from Bend to Mt. Bachelor, including KEEN Explore hiking sneakers.

Nearly ten years later, you will find a list of small or big adventures hanging on a large piece of paper in my bedroom. On this list, I have written down and checked off running a 50K, getting my WFR (Wilderness First Responder certification), climbing Hood and logging 20 ski days in the backcountry. All of them are my mini summits or accomplishments I like to hold myself accountable for, and if I don't write them down where I can see them every morning, I'd probably forget about them. Last winter, I added 'Bike to Bachelor and Ski Down' to the list. I manifested this by thinking about a genuinely human-powered mission that incorporates my three favorite activities, biking, hiking, and skiing.

Finding buddies to do this with me wasn't hard. Both my friends grew up in very active families and enjoyed being outside at any cost. Hail, rain, too much sun, or whatever! I've skied and biked with both of them, but not at the same time, and not using a bike as your main transportation to ski. We didn't have PROPER gear, but I wouldn't say you need niche equipment to so this. We were biking in sneakers, used bungees to hold our skis to our bike, and barely had a bike pump that worked! We were on a budget, but it didn't stop us.

I mapped out the route we would take, up to the mountain, and back down trying to avoid gravel roads. We only turned around once, after hitting gravel, for the sake of our sanity and the build of our road bikes, which probably shouldn't be carrying skis in the first place let alone riding gravel!

I knew this ride would be challenging, but not this difficult. We were working so hard; I couldn't even keep up a conversation with my friend Robin biking next to me. We were trying to balance staying out of the sun and taking water/food breaks while avoiding mosquitos in the shade. Oh, we also forgot the sunscreen! But we made it! Finishing the uphill bike portion with zero flat tires and still some humor left in us for some time around a night fire, we had no problem falling asleep.


Members of Kelsea's family took the easier route to Mt. Bachelor, driving a van to meet her there so they could all camp together.

The next morning we started touring, which is basically hiking with skis and skins (traction) on our ski boots while the heel pivots up. We had sunscreen, but it didn't take away from the sun damage yesterday, so we just covered up and continued on the snow. Everything was smooth, except the winds picked up as we neared the top, and balance was arduous. At one point, it was too dangerous to continue on our touring skis. We took our skis off and attached them to our backpacks while being blasted by pretty strong winds, boot packing on an icy surface at a 35-degree (or so) slope. For my friend, Mary, this was her second time being on touring skis. Her first was climbing Mount St. Helens, and this was a bit icier and steeper. The most stressful part of our trip just for the sake of not falling. But we made it.

We only stayed at the top for a few short minutes, snapped pictures, and took off for one big run down. At this point, it meant, ALL THE WAY DOWN — no more uphill. Just a pure earned run. The skiing was so great, even better that we came from Bend. We smacked our poles as each one dropped into the bowl from the summit and took off, forgetting the pain of what it took to get up there. We got to that parking lot, grabbed our bikes and chatted with some people who had seen us for portions of our uphill journey. They cheered as we rode off down to Bend, an amazing, no-pedaling coast into a local brewery for some brews.

I couldn't help but feel slightly sad when we finished. I wanted more! Even while we were biking up, we were trying to figure out what we would do next, and the cycle keeps going on. We schemed up our next "suffer-fest" for the future as we sat in the brewery.


Some adventures, you can't explain why you do them.


Some adventures, you can't explain why you do them. With good company, attitude, and mindset, we can accomplish more than we think. Our bodies are so powerful and adaptive! Small goals can add up, and if you count all the little days you have, you'll soon reach your 1,000-mile summer too.


Photographer Kelsea De Filippis was a KEENtern in the Creative Services department at KEEN headquarters. This annual program brings about a dozen students from around the world to Portland, Oregon, for a 9-week paid internship—and some never leave! We currently employ six of our former interns, and we love keeping in touch with the rest. You can learn more about Kelsea's work at www.kelseadphotography.com.

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