“Where exactly was the last big climb? Could I have already climbed it?” After backpacking a continuous 39 miles almost nonstop, I was understandably tired, and my reasoning was fatigue-compromised. Moments ago, I had left the last of two hiker challenge checkpoints, and the Pennsylvania finish line was only five miles away. I had hiked this section several times and knew there was a final climb that always hit me where it hurt. However, I couldn’t remember exactly where it was—and I was too tired to check my map.
I tried to rewind the past few miles in my mind. I had completed a climb immediately after the checkpoint and concluded that must have been the dreaded one. “That wasn’t so bad,” I thought. I congratulated myself for sticking to my fitness program that kept me in superhero strength. Nothing but a long descent and a final push through a boulder field to the Pennsylvania border!
Then I crossed a gravel road and saw the trail take a decidedly steep uphill grade. Rats! I now remembered—this was the last big climb. As I gaped at it, a couple hiked downhill in the opposite direction.
“Hi! How are you?” the woman asked cheerfully.
“I’ll be better after this climb,” I replied.
“It’ll be over before you know it,” she said brightly as she and her companion glided onward.
I rolled my eyes and took my first step. I regretted not bringing an “emotional support beer.”
The Challenge
DC UL annually runs a special backpacking challenge: wake up in a tent in Virginia and, within one day, backpack 44 miles on the Appalachian Trail to Pennsylvania, crossing the boundaries of Virginia, West Virginia, Maryland, and Pennsylvania—a true 5-State-Challenge!
This year, Emily generously volunteered to organize the complex logistics. She coordinated the shuttle and set up two checkpoints with bailout vehicles at each one. (Someone always needs to bail due to exhaustion or injury—this is a hard challenge.) Manning the checkpoints were Shane (“Dad Joke”), Chandler (“Willy Wonka”), Adam, and Devin. They provided humor, encouragement, rest chairs, and treats.
Unsure if she could hike 44 miles all at once, Emily led a shakedown hike a few weeks prior—featuring a 30-mile day. I didn’t go and lightly discouraged her from doing it. I told her not to get scared of the 5-State-Challenge if she felt worn out afterward. Backpackers suffer three unusual psychological maladies:
1. Backpacker Amnesia – This is when, immediately after an exhausting climb or trip, one thinks, “Okay, that wasn’t too bad.” One instantly forgets the pain!
2. Backpacker Severance – This is when your non-hiking “outie”-self signs your hiking “innie”-self up for a grueling trip, knowing the “outie” won’t have to hike it. Evil!
3. Backpacker Framing – This is when a hiker’s fatigue rises to match the planned length of the hike. If one plans to hike a 25-mile day it is much easier to do so than to plan a 10-mile day that you then need to expand to 25 miles while on the trip.
I told Emily her 30-miler would trigger that third malady: after 30 miles, she’d find it impossible to imagine hiking another 14. But if 44 miles had been the plan all along, she’d have no trouble. I didn’t want Backpacker Framing to scare her away from the 5-State-Challenge. She responded that she didn’t subscribe to much of my backpacking wisdom—like my other theory that night hiking equals free miles: if you can’t see them, you can’t feel them.
The Start
We staged the challenge Friday night near Harpers Ferry, WV. The Virginia/West Virginia border is three miles south of town, so by headlamp we hiked up to Loudoun Heights and set up camp. Eleven of us signed up for the challenge, ultimately arriving in two main groups—one at 7:00 p.m. and another at 10:00 p.m.
I was with the earlier group. As we hiked up to the border, I chatted with my companions. Mai (“Goldilocks”) had an impossibly small backpack. She planned to cowboy camp, which left plenty of room for what she called her “emotional support beer.” She carried it with no intention of drinking it before bed—or even during the long hike the next day—unless it became an emergency. Just having it comforted her. I thought it was a heavy vanity item. I would later envy her planning.
The two of us, plus Ju, Robert (“Art Vandelay”), Austin, and I hiked the 1,000 feet of elevation gain together. We were supposed to arrive after the second wave (because we had shuttle duty), but epic traffic delayed the others by over three hours. On the way up the mountain, we saw Brian hiking towards us the wrong way down the trail. He arrived first, thought he’d gone too far into Virginia, so he turned around to find the border. He was mistakenly hiking back into West Virginia. Upon seeing us, he turned and joined us, retracing his steps to the border.
We made camp and went to sleep at a very reasonable time—before 8:00 p.m. I slept so soundly I never heard the second group arrive.
The Hike
I awoke and broke camp to start hiking at 2:30 a.m. Others started then too. I later learned many of the late-night crew began just after midnight. Art Vandelay started last, at 3:00 a.m. On the descent from Loudoun Heights back to Harpers Ferry, I briefly hiked behind Goldilocks and Ju. They let me pass, and I knew I wouldn’t see them again until Pennsylvania. Ju was new to backpacking. Her heavy-looking pack and precariously attached heavy, bulky tent seemed ready to fall off at any moment. I pitied her for carrying such a load for 44 miles. Goldilocks was weighed down with her “emotional support beer,” which was clearly slowing her down.
The first three states came early. By camping on the Virginia/West Virginia border, we bagged those two states in a microsecond. I hiked alone in the dark through the ghost town of Harpers Ferry and crossed the Potomac River into Maryland—the third state. “Just one more to go,” I thought. “This 5-State-Challenge is mine!”
After hiking three miles on the flat C&O Canal along the Potomac, the trail climbed to a ridge. Just before Gathland State Park—the first easy water stop—I heard rustling behind me. Expecting deer, I turned my headlamp and instead saw a flashlight beam bouncing down the trail. I didn’t need to ask ChatGPT if deer use flashlights to realize it was another hiker—probably Art Vandelay or Brian.
However, Ju soon passed me, smiling as her big tent bounced loosely with each step. I tried to keep up, alternating 20 paces of hiking and 20 of jogging, but it wasn’t sustainable. “It’s okay. This isn’t really a race,” I thought as Ju disappeared down the trail ahead of me.
At Gathland, I refilled my bottle from a handy faucet. Another hiker strode by without stopping—probably Brian or Art Vandelay. I called out about the water, but he didn’t hear or didn’t need it. Shortly afterward, after I had chugged a half liter of water, Austin appeared, and I gave him the DC UL “FU greeting”: a bright “Hi!” as I hefted my pack to leave immediately upon seeing him. This might not be a race, but I didn’t want to lose!
Eventually, I caught up to Maddie, who had started just after midnight with the second wave. We chatted about her recent marriage. We’re close enough friends that she had initially proposed to her then-fiancé that they have their honeymoon on a DC UL backpacking trip I had posted. The suggestion was not as well received as she expected. In an early act of marital compromise, she agreed to do something more traditional when her fiancé asked her, “WTF?”
The Checkpoints
Eventually, Maddie fell behind and I hiked alone until the first checkpoint at I-70. Emily, Alyssa, and Ju were relaxing on lounge chairs as Dad Joke, Willy Wonka, and Adam plied them with sugar. I sat and enjoyed the break. On the check-in sheet, I saw that Beth, Brian, and Art Vandelay had already come through. Dad Joke said none stayed long.
Knowing the miles wouldn’t hike themselves, I made a shorter rest stop than I would have liked and hiked alone for the remainder of the challenge. At the final checkpoint, I saw Ju leaving and Austin arriving. Exhaustion was creeping into my legs. When I’m tired, I suppose my feet shuffle, because they kept striking rocks. It started to hurt. I knew I’d lose toenails from this.
The 5-State-Challenge section of the Appalachian Trail has 7,300 feet of elevation gain, but over 44 miles, the grade is relatively gentle. The rocky sections, though, are relentless and 44 miles are, ahem, 44 miles—and that’s what makes it hard.
The Finish
After completing the last big climb (which really was over before I knew it), I started quickly hiking the flat, plateau-like summit. I knew Raven Rocks—a very steep, rocky descent—was my last big obstacle. It is cliff-steep, so one must climb down slowly. At my pace, I hit it in full daylight, though. That makes it easier. After that, only a short hike through a final boulder field to Pen Mar Park and the Pennsylvania border. Though just three miles, it always feels endless.
But end it did. I soon passed the park pavilion, cheered on by Beth, Brian, Dad Joke, and Adam. I tagged the actual Pennsylvania border three-tenths of a mile beyond, then returned to wait for the others and celebrate.
Brian reported the fastest time this year—somehow finishing an hour quicker than me. Art Vandelay was an easy second place, followed by Ju. My average pace was three miles per hour over 44 miles, so I wasn’t exactly lollygagging. But Brian’s slightly faster pace added up. It didn’t matter, of course—this wasn’t a race.
Eventually, everyone arrived, and we all celebrated over pizza and beer. All eleven backpackers finished—unusual for this challenge. Even more unusual, women made up the majority of the crew this year—a DC UL first. We completed the challenge strong, with no injuries or major hardships. Goldilocks didn’t even drink her “emotional support beer”; it simply comforted her as she crossed five states, as intended.
Epilogue
Satiated with two large slices of pizza and an exercise-addled brain, I hiked back to the Pennsylvania border, then another half mile beyond to camp by a gentle brook. As I lay on my air pad in my tent, comfortably snuggled under my down quilt, I reflected on the five states of the 5-State-Challenge I hiked that day: Virginia, West Virginia, Maryland, and Pennsylvania. I woke up in a tent in Virginia and went to sleep that night in a tent in Pennsylvania.
Some wag might point out, “Hey, that’s only four states!” But as my eyes closed and sleep overcame me, I relished the fifth state—the state of exhaustion.
— David O (“Spider-Man”)
Cover Photo Credit: Dad Joke (Not pictured: Spider-Man)
DC UL Backpacking 
I’m holding my emotional support beer in the picture! It tasted like heaven after 44 miles!
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