What was meant to be the most grueling part of the Appalachian Trail turned into a nightly pizza party with great friends and an unexpected gift in the form of former thru-hiker, Black Bear.
“And once you were lost in these immense woods, you would die. It was as simple as that.” – Bill Bryson, “A Walk in the Woods.” His reflection of the 100 Mile Wilderness.
There are two locations on the Appalachian Trail that hikers fear above all others: The White Mountains of New Hampshire and the 100 Mile Wilderness in Maine. The White Mountains are known for their extreme trail conditions and unpredictable severe weather while the 100 Mile Wilderness is the only place along the Appalachian Trail where there is no resupply for 100 miles. To put the 100 Mile Wilderness in perspective, everywhere else on the trail has resupply points every 25 to 50 miles, and especially through New York and Connecticut, you can resupply throughout the day at the various delis, convenient stores, and gas stations found close to the trail.
All that to say, the 100 Mile Wilderness was intimidating. I had never carried a 5 or 6 day full resupply before. Plus, there are no outlets through the 100 Mile Wilderness to easily get off the trail if something happens to you. All along the first 2100 miles of trail, there are many paved, well-traveled highways that you cross, but not so in this section of the trail. I wasn’t carrying any kind of SOS device so I’d have to be extra careful not to do something stupid and get hurt. There are forest service roads all throughout the wilderness area, but the cars and trucks coming through there are few and far between. For nearly five months of hiking, these details ran through my mind as I tried to think about how I was get through this section in one piece.
In late September of 2022, the moment had finally arrived. I was a few days out from Monson, Maine – the last trail town before the 100 Mile Wilderness, and I was trying to my best to get my mind in the right space to prepare for what was quickly approaching. I was feeling mostly positive about it. I mean, after 2100 miles, I had learned a thing or two about backpacking and developed a good relationship with suffering and enduring. However, there was still a small piece of me that was a little unsure of the unknown of the last 100 miles. I was mostly worried that I’d run out of food.
But first thing’s first, I had to get to Monson.
I’d been hiking with my good friend’s Riverbutt and Rico Suave for several weeks, and we were planning on finishing the trail together. Riverbutt and I had especially gotten close as we had hiked nearly every day together for almost a month and a half. Our group was having a problem though, and the closer we got to Monson, the worse the problem got: Riverbutt was having excruciating foot pain.
Riverbutt spent the last 10 miles limping into the roadside trailhead where the highway ran less than 3 miles into the small town of Monson. Fortunately, I had made arrangements a few days before to get picked up at the trailhead. My buddy Patch, who I had made friends with in North Carolina and hiked with for a few weeks in Virginia, had told me to reach out to his parents once I got to Monson. They lived close by, and he had told me they love helping hikers when they can. So, I decided to take him up on that offer, I reached out to his mom, and sure enough, there his parents were waiting for us when we got to the road.
“Hi! I’m so glad you called! It’s so nice to meet you. Patch has told me all about you. My name is Emily and this is my husband, Bruce. Or if you want to use our trail names, I’m Black Bear and this is Batman,” she said as we came hustling across the road to the parking lot. Emily, or Black Bear, had thru-hiked the Appalachian Trail twice, and her husband, Bruce, had accompanied her in a few sections where he was able to earn a trail name for himself as well.
They were the kindest people. As smelly as we were, they hugged our necks and made us feel like family. I felt kind of bad that I had texted them just to come pick us up, and was sad that my only interactions with them would for another 20 minutes or so. They were the kind of people you meet and hope you stay friends with forever.
“Let’s get you guys to town. Hop in the car,” she said with a smile. She and Bruce were so excited to help us get to town.
As we started down the road, magic happened.
“So, how’s the hike going? I am so excited for you guys to be here! You’re almost done,” she asked, eagerly awaiting our answers.
As tired as we were, Rico and myself chatted here and there about how great the trail was and the bittersweetness of it almost being over. We were in some ways ready, but also, the trail had become our life at that point so it was going to be weird going back to “normal life.”
“That’s awesome! I’m so glad to hear that. What about you Riverbutt?… Riverbutt? Hey, are you okay?” She asked with genuine care.
Of course, everyone in the car was now staring at Riverbutt. He was on the verge of tears.
“I’m sorry,” he said. “I don’t mean to be dramatic or act like a baby, but my foot hurts so bad. Those last ten miles made the pain in my foot so much worse. I really don’t think I can keep going.”
The mood shifted. We couldn’t finish the trail without Riverbutt. This was serious now. I was even getting sad thinking about having to say goodbye to my good friend this close to the end.
But then, Black Bear came to the rescue.
“I will not let you quit this trail,” she shot back in defiance of the odds. “I will help you. What do you need from me?”
We were stunned. Was she serious?
“Uh, I don’t know,” replied Riverbutt, a bit taken aback by the sudden gracious offer.
“Are you guys planning on taking a zero at Shaw’s?” She asked.
“Well we weren’t sure,” I said. “What do you think, Riverbutt. If we took a zero, that might give you a little time to rest and get your foot feeling well enough to keep hiking.”
“Yeah I don’t know. That could be a good thing for me, but I’m not sure it will work. But yeah, we definitely should take a zero, just in case,” replied Riverbutt.
“Ok, here’s what I’ll do then,” said Black Bear, ready to make a plan. “I’ll go home, and see what I have going on this week. I don’t think I’m too busy. Hey honey,” she said looking at Bruce now. “Would you be good if I spent a week in the woods with them? Like I say, I need check a few things, but I think I can make it work.”
I’m not sure she was asking for permission, but it was a kind gesture to her husband.
“For sure! They’d probably appreciate it,” said Bruce.
“Then it’s settled. How would you guys like me to slack pack you through the 100 Mile Wilderness? That’ll take the pressure of all your gear and food off your shoulders, and you can really take this section slow so you don’t aggravate it,” she asked excitedly.
“You do not have to do that,” we all quickly responded in unison. It was such a kind offer, but it felt far too kind to accept.
“No, I insist!” Black Bear said emphatically. “I do this pretty often for people, and it just so happens that I have the time. I’d love to spend some time in the woods and help you guys out. I’ll even bring you guys pizza every night. How does that sound?”
We didn’t know what to say. This was better than Christmas morning.
“Yeah, that sounds great. Thank you!” We replied, still trying to wrap our heads around what we were just offered.
“Awesome! I’m so excited! And look, we’re here. I’ll text you tomorrow, Mav (That was my trail name, Maverick), and let give you an itinerary for roads I will be at for you to camp at. Sound like a plan?” She asked as the car rolled into Shaw’s Hostel.
“Sounds like a plan. Again, thank you so much. You didn’t have to do that for us,” I replied wondering how I could return the thanks for such kind help.
“It’s no problem at all! I love doing stuff like this,” she said, genuinely happy that she could come with us on the last part of our adventure. “Now, go on in and get a good bite to eat and some sleep. We’ll talk tomorrow.”
We spent the next day gathering our resupply as we tried to soak in the last hostel experience as well as reflect on our journey to this point. We ran into many old friends, including Buff and Buttflap who were waiting on us to arrive. They were some of our close friends who had gone ahead of us, but had regretted leaving and wanted to finish the trail as a tramily. We were glad to seem them and were so glad they waited. We told them what we were planning to do, and asked Black Bear if it was cool if two more people tagged along to our slack packing plan. She agreed and was excited to have two more join the crew. It was going to be like a fun little group camping trip.
The day after our zero, she arrived around mid morning to pick us up from Shaw’s. We said our goodbyes to all our friends and hope we would see them at Katahdin. We got our gear situated, filled our packs with only the essentials for the day, and headed toward the trail.
“Alright everybody, I’ll see you in about 15 miles. Riverbutt, how’re you feeling? Don’t overdo it on that foot,” said Black Bear.
“It’s feeling much better today. Thank you! I’ll try not to,” he replied.
“Black Bear, you’re more like Mama Bear, and we’re your cubs,” said Buff, somewhat jokingly but also seriously.
Black Bear blushed. “Aw, thank you. That’s very sweet. I just love doing stuff like, and I love that I get to be Mama Bear for a few days. I’ll see you guys at the end of the day.”
And so we went into the unknown, and what a time we had.
With Black Bear’s help, we weren’t intimidated at all. In fact, we were the opposite. We were elated. We were in no rush. We were enjoying the beauty of Maine in peak leaf season. And most importantly, we were enjoying each other. We had bonded as great friends in such a short time, and now that was coming to an end. We couldn’t let these moments be taken for granted.
Our first day was spent walking through beautiful birch and maple forests as the leaves turned vibrant shades of red, orange, and yellow. As we climbed mountains, we drifted into alpine territory where the beautiful pine forests grow. We ran into other friends of ours along the way, and sat to enjoy their company.
We eventually came to a gently rushing river that we had to cross using a rope system that had been set up across the 75 foot span of water. We cheered each other on getting across, hoping none of us would fall in and be swept away.
Later that evening, we made it to our first camp where Black Bear was waiting for us with a personal size pizza and a camp fire built. We sat around the fire in lawn chairs she had brought for us and reminisced on stories from the trail.
This became our routine every day. We’d wake up, hang out around camp for an hour, make breakfast, load our stuff in Black Bear’s car, and head down the trail for another 15 miles. We climbed up and over more mountains, crossed more creeks, and continued to soak in the last days we had on trail. The land around us was unbelievable. As far as the eye could see there were mountains, lakes, rivers, and forest without a man-made structure in sight.
Eventually, Patch, Black Bear’s son and my friend, came to hang out with us. He had finished the trail a few weeks before and wanted to spend some time with us before heading back into “normal life” too. One morning, he made breakfast for us on the small grill he brought from home. Our campsite that night was beautiful. It sat right on the edge of a river that was lined by birch and maple trees in their peak fall foliage.
Our conversations typically revolved around funny stories from the trail, Riverbutt telling a joke – which he did often, and making fun of me for all of a sudden developing stomach issues at the very end. Honestly, it was pretty funny – but I might’ve had a serious problem – because all of sudden, when I had to go, I had to go. Whenever people saw me throw off my pack and run into the woods, they knew I didn’t have long and it was a big joke to see if I would end up pooping my pants. Thankfully, I never did, and as annoying as that was, it was pretty funny.
Black Bear would tell us stories from the trail when she hiked. We learned about what had changed and what had stayed the same. She was so passionate about the trail, and we loved hearing her tell us about her experience.
The weather was also holding out wonderfully for us. The skies were mostly clear. The temperatures were cooler, but they were perfect. It would be 30 degrees in the night and get up to 60 during the day. There was absolutely no better place to spend the early fall days than where we were.
We were so lucky.
We were so blessed.
After 4 days of having the best experience in the 100 Mile Wilderness anyone has ever had, we had to say goodbye to Black Bear. She had something come up at home so she had to go back. We would have to spend our last night in the 100 Mile Wilderness without her and Patch.
“This has been the absolute best,” we all told Black Bear. “You’re the best, and we’re so thankful you did this for us. It really was a pleasure getting to spend this time with you.”
“Oh, don’t mention it,” she said humbly. “I really enjoyed you guys as well. You all were so fun to be with. Now go finish the trail. The best part isn’t too much farther ahead.”
And with that, we said our goodbyes and made our way down the trail. It was a bittersweet day. We had thoroughly enjoyed our time with Black Bear. All the fireside chats and pizzas with the best company around made the 100 Mile Wilderness the best experience I had on the trail. It was the perfect ending to an unforgettable adventure.
As night neared, we made our way up a small mountain, and gaped at the view that opened up before us. Set underneath the most beautiful cotton candy skies and above the fall foliage of the valley, was Mount Katahdin in all it’s glory. We sat in silence for a long time just taking it all in. It was overwhelming. The joy of such a perfect last few days combined with the end of an epic adventure were almost too much to handle. We hugged each other, laughed together, and told each other how thankful we were to be there together.
We found a nice little spot tucked away in the pines behind us to lay out our sleeping pads to cowboy camp for the night. As we lay there next to each other, I couldn’t help smiling to myself feeling grateful for the moment I was in and the friendships I had made along the way.
We would go on to finish the trail together a few days later, and next thing we knew, Black Bear was waiting there for us at the end with some of our families. We celebrated the end of our experience with some of the best people we had met along the way, and we were so thankful to close out this chapter with the one who had helped us finish strong: Black Bear.
I often think about the 100 Mile Wilderness and my time in it. I had the best time and spent it with the best people. I will always remember the fun we had and the help we received.
It was a gift. Being able to spend the last few days with the people I had grown to love. No complications. No long food carries. No stress. Just enjoying each other and soaking in the beauty around us. Thanks to Black Bear, what was meant to be the final daunting task of the trail turned into the best week I had since Springer.
I will cherish that time forever.
– Ralston Drake
Thanks for reading! I hope you enjoyed it as much as I loved experiencing it and sharing it. Be sure to subscribe for free below to be sure you get a notification whenever I post a new article. Thank you again! I hope your next adventure is one to write about some day too!
Wandering with Ralston 
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