The Rainy Season (CT through MA)

New York

Just as a quick refresher, the last section of New York was easily the worst maintained part of the entire trail. I remember walking through chest-high weeds/shrubs that covered the trail, scrambling over broken boards, and crawling on all fours (with my pack on) to get under fallen trees; all happening in the rain and mud as well. It seemed like the last time someone checked in on trail conditions was several years back. I had lost my group of friends I was with at this point because they had all ventured into NYC, while I decided to hike on. All the more fun to maneuver these obstacles with no one else to complain with. Little did I know, I was just beginning the wettest stretch of the entire trail.


Connecticut had a good chunk of just about everything for only 48 miles of trail. The area was more urban than preferred, but that’s the same story as the rest of the mid-Atlantic. The trail followed alongside the Housatonic River for several sections, including a relaxing 5-mile flat stretch. Although, the most memorable part of Connecticut were the PUD’s (Pointless Up-and-Downs). There were so many times where the trail would jump straight up a hundred feet or so, then immediately go straight back down on the other side. There were still enough boulders that these PUD’s would require And there would be stretches where these PUD’s were one right after the other for miles, like riding a rollercoaster except you have to physically work for the ‘thrill’ of going over a hill. As I mentioned earlier too, it rained a lot in Connecticut. Not every day, but enough to keep your gear damp, wake the bugs up, and keep the rivers rushing. In fact, I actually had my first major river ford in Connecticut.

Decided to cross this bad boy barefoot
The disregarded warning and bypass trail. Gotta hit all the white blazes!

The final stretch of CT was definitely my favorite section. The trail descends into a heavily wooded ravine while running along a river for the last few miles. The way the light shown through the tree cover, casting shadows and glowing beams of light all across the trail, seemed almost dream like. Sages Ravine was incredible. A section hiker advised me prior to my descent into the paradise that it reminded him of Rivendell from Lord of the Rings. I couldn’t agree more. I decided to spend my last night in CT in the ravine. It rained all night and my tent flooded out, again. But the next morning in the ravine made up for it. There was still a nice morning haze across the ravine which added all the more character to the beams of light peaking through and giving life to the trail.

Jennifer Pharr Davis – Becoming Odyssa

Jennifer Pharr Davis (JPD) is an AT legend and absolute beast of a hiker. In 2005, she through-hiked the AT for the first time after graduating college. In 2011, she set the overall (both female & male) fastest known time on the AT finishing the trail in 46 days (roughly 47 miles/day). She has accumulated over 14,000 miles hiked by through-hiking several other trails across the world, while setting many fastest known times along the way. In 2011, she was appointed as National Geographic’s Adventurer of the Year. She currently resides in Hot Springs, NC, where I actually ran into her providing trail magic to hikers as we passed by her house. I am bringing her up because my parents bought her book Becoming Odyssa: Adventures on the Appalachian Trail as a gift after finishing the trail. The book follows her journey of her first through hike of the AT in 2005. I have been blown away at her ability to put into words the way the trail communicates with hikers. She is spot on with the emotional, social, physical, and mental challenges I encountered on trail. So, if you readers are interested in learning more about the AT and different perspective on the experiences hikers encounter, I highly recommend reading her book. Obviously, with her hiking the trail 16 years ago, and each hike being different for every hiker, there are things she runs into that I never encountered, along with her hiking insane miles relative to what I did on my hike. She is a huge inspiration for hikers and people all over the world, and a great author as well. Below is a link to her website and book.


Becoming Odyssa: Adventures on the Appalachian Trail


Also known as Massa-Two-Shits. I had a friend who created a challenge of only taking two massive shits on trail the entire time through Massachusetts. The state has about 90 miles of trail, so only taking two poops is nearly impossible. Legend has it that she completed the challenge. Every time I read or hear Massachusetts I can’t stop thinking of Massa-Two-Shits and it’s ridiculousness.

Massachusetts was nothing but rain and mosquitoes. I swear it rained everyday, at least once. Unfortunately for us hikers, the state was experiencing record levels of rain for the month of July. I was always wet, carrying damp to sopping wet gear through the whole state. For some reason, the trail always has something worse to throw at us up ahead. Every time we hit a wall and think ‘it can’t get any worse than this,’ it does get worse somehow. This was one of those moments. Massachusetts wasn’t supposed to be hard, but the only thing I remember was the rain, and all the repercussions that come with rain in the woods.

After encountering the muddy/swampy conditions of southern MA, my buddy I was hiking with and I decided it was time to get into town and escape the horrors of the trail. We made it to the road crossing just in time for our friends to be driving by with a trail angel, pull over and pick us up, and take us to dinner, right before it started dumping on us all over again. When we arrived in Great Barrington, MA, it seemed like every other hiker in a 50-mile radius had the same idea, and hitched into town before the two days of rain. Every hotel was nearly booked and ridiculously expensive. Fortunately, I had accumulated enough hotel points over the last year I was able to reserve a room for two nights for free. We spent the next day in our hotel room watching TV, enjoying town food, and staying dry while it rained outside all day. Unfortunately, the next morning when we set back out to trail we had to deal with the consequences of all the accumulative rain. Here is a brief series of one of my most iconic mornings on trail…

Literally within 50 yards from leaving the road crossing, the trail was looking like this. I knew right away it was going to be an interesting re-entry to the trail.

As I progressed further, the water depth got deeper and deeper, the mosquitoes got more vicious, and I just kept thinking ‘it can’t get worse than this.’ Little did I know, the AT can, and will, always get worse before it gets better. Not only that, all the precautionary structures (like these flood boards) to help in such situations, were utterly useless.

As mentioned previously, this bridge appeared like a sweet escape from the flooding, but it didn’t last long. The water was so deep at this point I could literally see small fish and tadpoles swimming around my feet, on trail. And I’ll remind you, every part of my exposed skin was getting attacked by mosquitoes. The only safe place for my skin was under water.

The water now reached my pelvic area. No place was safe. I was literally wading through the water, hoping that I was still stepping on the trail and not on any loose logs and rocks.

I made it through the 0.5-1 mile long stretch of trail with no major problems. In fact, because I was so blown away that I was wading through the flooded trail, it didn’t even bother me. It was so insane that I enjoyed the excitement of it, rather than basking in the sorrow of being wet on trail. Once again, I reminded myself, no way anything will ever be as crazy as this. And to an extent, I was finally right. I never did encounter water issues this bad again, (but rather more physically demanding obstacles waited ahead…). Later that night, I arrived at camp and checked social media to see that the ATC had closed and rerouted this section of trail earlier that day. I had other friends who hiked through this same section today and dealt with the flooding as well. The water level was so variant, though, that friends who hit this section the day after, or even the day before, said that the water level never got deeper than ankle-high. To this day, I will always remember how I had to wade through waist-deep water after leaving Great Barrington, MA.

The rest of Massachusetts, was fairly uneventful. It was still wet, muddy and raining, but nothing quite like the flooding of Great Barrington. It was manageable.

I did get to spend a wonderful afternoon with some great friends canoeing at Upper Goose Pond, basking and swimming in the sun. We had decided to stay at a specialty shelter that was actually a 2-story house with a lovely caretaker couple. The next morning the couple made us all pancakes and coffee for a small donation to ensure supplies for the next round of hikers. Of course the side trail to the shelter was flooded with ankle deep water. So we knew we’d be starting the next morning out with wet feet… classic.

Upper Goose Pond

The final mountain in Massachusetts, Mount Greylock, was incredible. It was the first time, in what seemed like forever, we were back in the mountains. I remember stopping near the summit because the trail was completely silent. No cars, no planes, no muggles, no birdsong, and no wind; this pure solidarity was one of the reasons I came to trail. It was just me and the woods. It made me so happy to know that the trail was escaping the commotion of the mid-Atlantic and reentering the peace of the wild I had craved when hopping on trail.

The summit had a beautiful lodge where my friends and I stayed in a bunk room. It was the perfect spot to shower, eat dinner, and enjoy a beer with friends while looking down at the world below. There’s also an iconic obelisk that allows 360 views of the flatlands of Massachusetts and the Green Mountains of Vermont. We could see it, the great peaks of real mountains again. Intimidating, but welcoming as well; I knew I was headed in the right direction.

The next morning, my friend and I both awoke early to catch the sunrise. The last one of Massachusetts and the mid-Atlantic. But also the first sunrise of the final quarter of trail, my favorite section, and most challenging of all. The promised land of the AT was waiting for us.


One thought on “The Rainy Season (CT through MA)

  1. I can remember telling my second graders to stay on the blacktop and out of the mud during recess . . . clearly my warnings were wasted on YOU, Seany Markey!! What an adventure! I think I would have hitchhiked to where the trail wasn’t flooded and rejoined you and your muddy wet shoes and socks there. I hope you’ll think about writing a book about this amazing adventure, Seany. You certainly have the skills and now the adventure to talk about. It would be so interesting for young people to read who are thinking about doing the AT and it would be a fabulous experience for you as well. Just a suggestion but now, while everything is so fresh in your mind, would be great timing. Think about it. I am incredibly proud of your accomplishment but not at all surprised. Sending you blessings and the wish for new shoes and dry feet!

    Liked by 1 person

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