There’s a Party in Massachusetts: AT Flip Flop Days 54-62

Day 54

I felt rushed trying to get ready in the morning after my zero; I was determined to not fall behind Jingle and Subtitles again. We were dreading the climb up Bear Mountain, our last obstacle in Connecticut and the first time we would be above 2,000 feet of elevation. Our worries were overblown, as the climb to the top was quite easy. We took an early lunch break at the summit and admired our last view in Connecticut while basking in the warm sun.

The descent down Bear Mountain was more steep and a little technical, but it was over quickly. We crossed into Massachusetts and descended into Sage’s Ravine, a beautiful old growth hemlock forest along a creek. The bugs were thick, but the forest was stunning. 

Our first climb in Mass was up Mt Race. It was a steady climb, but again not too bad. Mt Race yielded the best views we’ve had on trail so far. After the summit, we again had a steep, difficult descent. We debated as a group whether to stay at the campsite between Mt Race and Mt Everett or continue to the next shelter. I was exhausted and my ankle was hurting, so I wanted to be done, but I didn’t say anything. We decided to push on to the shelter on the other side of Everett. 

Mt Everett was a hard climb, our third big (for us) mountain of the day. There was no view from the top or anywhere else on the mountain. The descent was even more challenging than the first two. Afterwards, Jingle confessed that she wanted to stop at the last campsite too. We made a signal to let eachother know when we are tired and need to team up to make Subtitles stop for the day. 

I limped into camp exhausted. Most of the good campsites were already taken, so Jingle and Subtitles posted up in the shelter. I found an ok hammock spot and didn’t bother putting on my rain fly. It had been a great day with the views and cool forest, but it was exhausting.

Day 55

I had trouble regulating my temperature last night and didn’t sleep well as a result. That has been the biggest challenge of the hammock, since there’s nowhere to throw off the quilt when I get too hot, and it’s harder to vent. I woke up tired and still sore as a result of the poor night’s sleep.

We had some moderately difficult climbs and descents to start the day, but the trail eventually leveled out and became easy. We did not have any big views like yesterday, but the forest and fields we walked through were gorgeous. I’m really enjoying seeing more evergreen trees, especially the abundant hemlocks, which are dying out in the South.

We stumbled upon some major trail magic around lunch time. They were set up under a giant tarp shelter that is set up at the beginning of the hiker season and torn down at the end of it. Churches and other organizations around Sheffield take turns running the trail magic there. We had burgers and hot dogs as well as some cool drinks and snacks. 

It was hard to get up from the trail magic, but we called for a shuttle and hiked another half mile to the highway that goes into Great Barrington. It looked like a cool town, but it was full of tourists arriving for their weekend stays. We camped at the Berkshire Community Center on the northern edge of town, which allows hikers to set up in their field and nearby woods for free. We hung out for a while and then went to the Great Barrington Brewery for dinner, since we had met the owner’s wife at the trail magic. 

We were all tired and decided to just resupply in the morning (the reason we came to town in the first place). My ankles were still bothering me, and the next stretch seemed challenging with the elevation and camping restrictions. I was still feeling a little down about my hike and whether I would be able to finish. I shifted my focus to concentrate on finishing the northern section of my flip flop. I was nearly half way to Khatadin, which seemed easier to wrap my head around than only being a quarter done with the trail. 

Day 56

I didn’t put up my rain fly last night, since there was no rain in the forecast, but I woke up at 4:30 to raindrops falling on my face. I cursed and got up to deploy my rain fly. It took a while to fall back asleep, but I woke up again at 7:30 to the sounds of Jingle and Subtitles taking down their tent. I hurriedly packed up my stuff to not fall behind. We walked over to the grocery store to resupply and then went to McDonalds for coffee and breakfast.

We had been leap frogging with another hiker, Heat Miser, since the beginning of New York. He stayed with us at the community center, but in the morning he told us he was going home for awhile. The heat was getting to him and he was feeling burnt out. I recognized that I was feeling the same way, but funnily enough I wasn’t feeling the same pull to get off and go home like I had been before. I felt proud of myself for choosing to stay.

The trail was nice and easy today, and we all cruised along quickly. We came across two different trail magic coolers and were happy for both of them. The highlight of the day was a place called Ice Gulch, a deep ravine in a conifer forest. It was stunningly beautiful.

Our goal for the day had been to make it to the other highway that goes into Great Barrington, 8.4 trail miles from the road where we started the day. At this second highway, we had heard there was more trail magic.

The Memorial Chapel AT Great Barrington, owned by “Sneak Attack” Sue and her self-described “avid indoorsman” husband Marc, go above and beyond to provide trail magic to hikers. They bought the property to eventually build their retirement home, but for now they come over on weekends to serve hikers. They took a suffering hiker to the hospital, and they gave us shelter from a storm on top of the great food and beverages they normally serve. If you happen to be passing through on a weekend when they are there, definitely stop by! Sneak Attack makes the best cookies.

Day 57

There were more storms in the forecast for the day, and we wanted to stay dry for as long as possible. We hustled to the second shelter to take our lunch and wait out the early afternoon storm. Our plan worked and we stayed dry. 

After the storm we hiked on. I’ve been moving faster the past few days, and I rushed ahead to camp. I think I’m getting trail legs? The trail today felt easy; there were a few big climbs, but they weren’t difficult. There was only one small view, but the forest was very pretty. 

Our campsite was at the site of an old abandoned Shaker settlement, reclaimed by the woods. It is now inhabited by mosquitos. We set up, ate dinner, and did our camp chores quickly to avoid the bugs. This proved to be fortuitous, as it began to pour at 6:30. We all went to bed early to stay dry. 

Day 58

I didn’t sleep very well. Some animal was roaming around camp all night. None of our stuff seemed to be disturbed, just my sleep. I was exhausted. 

Early in the day, we came upon a bench with a nice view and took a quick break. A short while later we came upon another one, but didn’t stop. At 1.5 miles into our day we crossed a road and hit the famous AT stand, where you can buy drinks and snacks. The trail was telling us to take it easy this morning. I bought a can of Mt Dew to help me wake up and a couple of snacks for second breakfast. 

After the early breaks, the hiking went by quickly. There was a boardwalk section through an open marsh that was reminiscent of the boardwalk in New Jersey, but this one wasn’t quite as nice. 

“We on a daggum puppy dog obstacle course!” -Subtitles

We were hoping to get to Upper Goose Pond Cabin for the night, but we arrived there around 1pm. I was super hungry, so stopping for the day sounded great, but after lunch, I was feeling much better. We debated whether to stay or push on. We needed to resupply, and the road to Lee was not much further. We got a room at a lodge/motel right next to trail, took showers, then got a ride into town to resupply. Lee has a list of free shuttle drivers, continuing the amazing trail magic in Mass. 

Day 59

It was great to stay inside and catch up on some sleep. We had a slow start to the day. After a big climb, the terrain was fairly flat for the rest of the day. However, there were a lot of roots to slow us down. 

We had two more instances of trail magic today. The first was totally unexpected at a dirt road crossing. They had a great sign in the woods, cold drinks, snacks, and a large net tent to get away from the bugs for a little bit.

The second trail magic was expected. We visited the cookie lady’s house. We had lunch in their yard, had some of their cookies and lemonade, and filled our water bottles. We even got to pet their dogs! 

Some of us suffered a sugar crash with all the trail magic today. Despite being flat, the roots made the 16 mile day feel difficult. 

We camped at a shelter tonight, and there were quite a few people there and surprisingly not many bugs. We stayed up a little later than normal chatting with people, having one of our first social shelter nights in a very long time. Goofing around at the shelters with other hikers is one of the best parts of the AT, and I had really been missing it.

Day 60

I still felt like crap when I woke up after the long day yesterday. However, the town of Dalton was only a few miles away, so I raced into town to get coffee and a real breakfast. The coffee shop there was ok, but I felt really out of place in my sweaty, stinky hiker clothes. 

Jingle and Subtitles missed the turn for coffee and ended up on the other side of town at Hot Harry’s Burritos. This place felt way more hiker friendly. They didn’t have coffee, but the owner went to the coffee shop and brought back what Jingle and Subtitles wanted at a much reduced price than what I had paid. We happily ordered some food from them and thanked them for the trail magic coffee run. 

I felt worse after town than when I woke up. I had some gastro issues and my chafing was coming back with the heat and humidity. I accidentally lost about half of my water while trying to clean myself up after having to make an emergency pit stop off trail. I felt lightheaded and nauseated. Every step was painful, especially after I rolled my ankle hard in a hole I didn’t see in an overgrown power line section. I prayed that I didn’t sprain the ankle, but it slowly felt better over the next few miles. 

In addition to physically suffering, my mental state was not good. I was frustrated that I felt so bad after yesterday’s 16 mile day. I didn’t believe I would be able to finish, and I didn’t feel like I belonged out here. I wanted to quit again. 

I got to camp and had an introspective evening, mostly keeping to myself, trying to get my head on right. I needed to accept my limits, stop comparing myself to the other hikers, and give myself some grace. I went to bed determined to have a better day tomorrow and looking forward to an unexpected visitor. 

Day 61 – July 4th

All through Massachusetts, we had been reading in the log book about a 4th of July party at Father Time’s house near mile 1600. We had a loose goal to get there, but we came up about 15 miles short. Crash and Boom Boom decided to do a long day up and over Mt Greylock to try to make it to the party. Jingle and Subtitles wanted to zero and catch a ride up there and back. 

I woke up with the plan to zero and catch the ride with Jingle and Subtitles. I thought maybe my unexpected visitor could give us a ride, but he had family obligations. We went to Dunkin for breakfast before making a plan. (We don’t think straight on an empty stomach.) After getting back to our camp, I decided to see if Bascom Lodge on top of Mt. Greylock had bunks available for the night, while Jingle called various shuttle drivers. We found that Greylock did have bunks and there was a shuttle driver willing to take us to Father Time’s and back, so both options were viable. 

I decided to hike on to Greylock on my own. It would have been great to walk to the party if our mileage had lined up for it, but I didn’t want to get a ride ahead and back just for the party. Getting ahead of Jingle and Subtitles would also give me some cushion to meet my visitor tomorrow and not fall behind.

I packed up and began the walk through Cheshire and up to Greylock. The climb was not bad at all for my first 3,000 foot peak of the trail. On the way up, I met a hiker named Restless. We leap frogged for a little bit and then ended up hiking together. Restless was also staying at the Bascom Lodge with her mother and grandmother. Her mother met us on the trail and hiked north with us. When we got to one of the first roads, we met her grandmother as well, who had set up trail magic. I stopped and had drinks and snacks with this friendly family.

I hiked on the last mile or so to the lodge. I got checked in and claimed my bunk before going up to the Greylock summit for some great views. I was sharing the bunk room with another hiker named Marathon, and I had a good chat with him while I prepared and ate trail food for dinner. He went down to join Restless and company for real food. I came down to have a beer with them while they finished dessert. Restless brought in the leftover trail magic and told us to take what we wanted.

Since it was the 4th of July, we stayed up and tried to get a good view of fireworks from the summit. We could see several shows off in the distance. It was cool to see them from a different perspective and without all the noise. 

Day 62

I slept great in the lodge and would definitely recommend it to future hikers. I took my time with breakfast and chatted with Marathon and Restless’ crew some more. I hadn’t heard from my visitor yet, so I planned to take my time going down Greylock and heading to the grocery store. The hike down the mountain wasn’t too bad. I heard back from my visitor about halfway down and made a plan for him to meet me at the grocery store so that we could go out to lunch.

I arrived at the grocery store at 12:30, exactly when I thought I would. My friend Sean from work was already there waiting for me. He just happened to be in the area visiting family for the holiday weekend, and it was complete confidence that I was nearby. I dumped my pack in his trunk, quickly changed into my non-sweaty shirt, and quickly resupplied for the next short stretch to Bennington, Vermont. We drove over to Williamstown to a nice Mediterranean restaurant. It was great to catch up and hear about back home. The restaurant also had some of the best falafel I’ve ever had. 

It started to rain as we drove back to trail. It rained harder as I got closer to camp. I found a spot to set up, and by the time I was settled, everything was wet. Jingle and Subtitles didn’t make it to camp, because they got invited back to Father Time’s for dinner while they were resupplying at the grocery store and then they found a motel to stay dry for the night.

We had gone through all of Massachusetts without a zero and without laundry. I was ready for a break, but I would have to wait a while longer to get that break in Vermont.

Lack-of-Shower Thoughts 

I loved my time in Massachusetts. The kindness and trail magic was abundant. The forests and mountains were beautiful. It has been my favorite section of trail so far. It was still hot and humid, but not nearly as bad as it had been in New York and Connecticut. I still had several instances of self doubt and wanting to quit, but overall these were not nearly as strong as before, and I found that I was enjoying things again more often than I had been. Massachusetts may have saved my hike.