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Last fall, a friend and teammate on the racing team I ride for in Brooklyn had vaguely expressed interest in riding the Oregon Outback. I told him I was 100-percent in and to let me know when he was committed. I kept bugging him about it every now and then until he let me know he was looking at flights. I had heard that a few other New York friends were going, so I bought a flight too—we were more than ready for an adventure after suffering through a long, cold NYC winter.
I’d never been to Oregon and knew nothing about the Outback’s route. We would discover every surface imaginable, from short sections of beautifully paved highway to completely rutted out and almost impassable wagon trails, cow paths and fire roads. So much of the riding was on unpredictable dirt, you constantly had to pay attention to the wheel in front of you and make sure you were following the right line to stay upright. Every time the road turned really nasty or I was at my maximum trying to get up another insane hill, I’d take a moment to look around and realize we were riding through some of the most unbelievably beautiful and untouched terrain any of us had ever seen: soaking-wet forests, bone-dry deserts, pristine lakes and reservoirs, rivers and creeks (that we forded or splashed straight through), and tons of mud. The variety of terrain in four days was amazing.
My preparation for the trip was minimal—I was still dialing in my setup at the hotel the night before we rolled out. Most people were doing the route on dedicated off-road touring/randonneur-style bikes or fully rigid mountain bikes. I used a steel cyclocross machine that had been collecting dust in my parents’ garage in California. The bike was mostly functional, but I hadn’t ridden it in six months, and never for a ride longer than two hours. The bags I strapped to it (containing tent, sleeping bag, food, camera equipment, extra water and so on) were not as functional as some of the others I saw, and I had tons of issues with the bags rubbing the tires when we went over rough terrain. Both wheels were out of true and rubbing on the brakes and I ended up having to use an older worn-out rear tire because the new one I bought for the trip wouldn’t clear the chain stays. Also, the hard leather Brooks saddle destroyed me in the first couple of days and I had to completely adjust my riding position to compensate. I was under-geared for some of the longer, steep loose-dirt climbs and I definitely brought too much stuff.
Day 1 started early. It rained on and off most of the day and I immediately regretted bringing my SLR camera, which I had to wrap in a plastic bag. Nonetheless, spirits were high and we hammered on whatever sections we could while our legs were still fresh. This day was our longest, riding 124 miles between 7 a.m. and 9 p.m. I was completely demolished by the time we stopped for the evening, and a little disappointed to discover we’d missed the turn for hot food at the Cowboy Dinner Tree—we ended up eating anything suitable from a convenience store (not too vegetarian friendly!) and sleeping in a barn garage on a friendly farmer’s property.
Day 2 began slowly, but we smashed it on some seriously beautiful roads that were said to be troublesome the previous year. A group decision to detour 14 miles for burgers and fried-egg sandwiches was totally worth it. Then, after ascending a steep paved climb we bombed downhill to find ourselves camping by a reservoir for the evening. Morale was high after completing our second century in two days.
Day 3 might have been the toughest for me. Every day was hard, but parts of this day’s route almost broke me, not to mention the saddle that was seriously affecting me. After riding alongside a river into town, eating a huge diner breakfast and drinking four or so cups of coffee felt incredible. Multiple water crossings, mud, extreme heat, seemingly endless paved and dirt climbs leading to an epic group campsite at Shaniko were the day’s highlights. My body was starting to wear down at this point but not nearly as bad as some of the other guys.
No one knew what to expect on Day 4, only that it was going to be the shortest in mileage but perhaps the most in elevation gain—certainly the most dirt. The rumors we’d heard of endless rollers and headwinds proved to be true. But we suffered through it, and ended the day with spirited attacks on the final paved descent into the Columbia River Gorge.
Riding up to 12 hours a day for four days straight taught me a lot about the body’s limitations. I came into the ride with a good bit of fitness from road racing but nothing could prepare me for the sheer amount of endurance required for the Oregon Outback. To ride for hours on end, you have to constantly be eating and drinking. Anytime we had an opportunity to sit down for a meal we took it, and the hours in between were fueled by tons of Snickers bars, questionable fruit whenever we could find it, coffee and oatmeal cooked over camp stoves, and lots of raw nuts and trail mix. I ate a bite of something every time we stopped or every time we crested a long hill.
I never ran out of food, but we came dangerously close to running out of water a couple of times. Most people had water pumps and we had a good idea about how long we had between potential water refill spots. I never cramped, even though I was definitely riding at my maximum many times each day. I did develop some ankle and knee pain from being under-geared for the longer climbs, which I had to grind out in my smallest gear while others were comfortably spinning up.
My theory on endurance cycling is that anyone can do it if you set your mind to it. It takes a certain amount of mental fortitude to ride hundreds of miles in a few days, but so much of the battle is in your head. The six others in my group were all accomplished cyclists in various disciplines, and we rode as hard and as fast as we could on certain sections just because we could, but I honestly think that anyone could do this route with the right bicycle and gear, and the willingness to complete it. The many hardships made the ride worth doing, and it would have been a lot less memorable if it hadn’t rained on us for most of the first day—but it was great to start the trip on an epic note.
My expectations for the ride changed in the first hour when the light Oregon drizzle turned to heavy rain. I had to figure out how to keep my camera dry so I could begin capturing the experience of bikepacking, this style of self-supported riding. The “gravel grinding” movement has gained mainstream notoriety in the last couple of years and I’m weary of seeing the same generic photos of a bike laid down on an empty expanse of forested dirt road. Instead, I wanted to take portraits and capture off-the-bike moments. But I’m already thinking about what comes next—and once you’ve completed a trip like the Oregon Outback you can’t stop thinking about getting back on the road.