7/4-7/12: Kent, CT -> North Adams, MA

I love New England. Hiking through the first two states here was a joy! Connecticut and Massachusetts were filled with beautiful scenery, quaint New England towns, an amazing number of wonderful trail angels, and some new challenges along the way, too.

When I got back on trail, it was Independence Day, but much more importantly, it was my four-month trailiversary. They keep coming faster and faster. Four months feels like a very long time, though.

It was a beautiful day, but hot, humid, and very sweaty, which feels like the new normal. After a short but varied afternoon of hiking, I was surprised and disappointed to be the only one at the shelter. I was hoping to be with other hikers that night. Between saying goodbye to Macy and my family, getting back into the swing of things on trail after a radically different zero day, and finding myself alone, it was a kinda weird mental day. Seeing fireflies light up all around me helped though 🙂

Thankfully, the next few days only got better and better. The next day felt all about the water. I paralleled the Housatonic River, glinting in the sunlight, in the morning. There were so many beautiful streams along the trail! It felt like a relief to see so many good water sources after they had been more sparse for the last several states. I also forded Guinea Brook, which was my toughest and deepest ford yet, though I still had no issue with it. The cool water felt great on a hot day. I still underestimated how much the heat and humidity would slow me down, that day and in days to come.

I also walked along the Housatonic the next morning, on a pleasant, rare handicap-accessible section of trail. I crossed 1500 miles right at a iron bridge over the river. It was definitely the coolest hundred-mile spot since Clingman’s Dome!

Soon after, I was awed by (creatively-named) Great Falls! They were perhaps the best falls since Amicalola. I was really impressed with everything the Housatonic had to offer; it may be the coolest river I’ve seen on trail.

That day was such a gorgeous and varied section. On Mt. Prospect, we had a spectacular vista of the Massachusetts mountains to come at Rand’s View. That was my favorite view in quite a while. I also passed by the unique rock formation Giant’s Thumb.

That afternoon, I walked half a mile into Salisbury, CT and back to resupply. It was a lovely, quintessentially New England (and yes, a bit expensive) town. While I was there, I got some cupcakes to munch on, and traded some for a beer with section hiker Flat Tire. I had a good time hanging out with him, and it made for a relaxing town stop on a great hero day.

To my dismay, when I got back on trail, I got hit by a passing thunderstorm going up Lion’s Head. It was intense, but short, and luckily it cleared up just in time for me to appreciate the cool summit! The whole traverse from Lion’s Head to Mt. Everett in MA was truly awesome.

That night, I stayed in a nearby shelter and had a lot of fun with a curious Scout group and an amusing former thru-hiker, Braveheart. I slept way in in the morning (after the fog thwarted our attempt to watch the sunrise from the shelter), since I knew I was doing a short day to facilitate a special meet-up on the following day. This made for a very different and frankly wonderful experience for the day.

I enjoyed the rocky summit of (another) Bear Mountain, the highest peak in Connecticut. It’s not the highest point in CT, though, which goes to a spot on the MA state line on the slope of Mt. Frissell, not on the AT. Epic boundary value moment.

The descent down from there was very steep and tough. Luckily, the bottom felt very rewarding, in several ways. First, I crossed into Massachusetts! It was so exciting to be back in my true home state and favorite state in the union. What turned out to be even more exciting, though, was the section that followed in Sages Ravine.

Sawmill Brook, bubbling through Sages Ravine for a mile or so, made for an absolutely spectacular sight. It was such a lovely, pristine place and I was so delighted by the atmosphere.

The excitement didn’t stop there as I climbed up again. The traverse over Mt. Race was awesome, featuring an extended exposed ledge. Finally, I climbed the steep ascent of Mt. Everett. They all felt like truly New England mountains – because they were! Luckily, I stayed dry throughout all of this, though it was threatening to thunderstorm for hours.

It finally rained lightly as I came down Mt. Everett, which was too bad, since I had been hoping to swim in pretty Guilder Pond. The poor swimming weather didn’t stop a local getting his laps in, though.

That whole day was one of my favorite sections of trail. I revelled in taking the time for long conversations with people throughout the day. First it was another thru-hiker Juneau at a shelter, then a former thru-hiker Thunderbuns (AT ’17), who also gave me passing trail magic in the form of clementines and a beer, then really nice locals at the pond, then finally a friendly wilderness adventure group camping with me in a beautiful pine forest. I loved being able to do that on a short day.

First thing in the morning, I found myself face to face with a Little Bear! This one took human form – my trail friend from way back in the Before Times! Her thru-hike story is an interesting one: she seized a great job opportunity in the middle of her hike, flipped up from Virginia to hike all of Maine, and is now trying to finish the rest of the trail on weekends and vacations. I was the happy beneficiary of this arrangement, as Little Bear joined me for the weekend to hike a section in MA!

It was so good to see Little Bear again. We had an amazing two days hiking together. It felt great to have another thru-hiker as a hiking partner for a while again. We certainly never ran out of things to talk about!

The two days we were together, Little Bear and I got up and out super early, leaving camp at around 6:15 am, which was easily a record for me. I really liked hiking that early and being able to make good progress before it got too hot.

That first morning, we got a big trail magic spread, including burgers and hot dogs, under a huge tent overhang thing. It was put on by a volunteer group that does this every Monday-Saturday for 8 weeks straight!

What’s more, while we were there, I heard from Gretchen, who offered to meet up later that day and do more trail magic for us! It was such a delightful surprise and lovely offer. We met up with Gretchen and her dad at our last road crossing of the day, and hung out at their trail magic for an hour and a half.

It was everything I’d hoped for. It was so, so special to see Gretchen – for the first time in a decade, we realized – and meet her dad, who had also thru-hiked with Gretchen and her sister in 2021! I was so glad to be able to thank Gretchen in person for all her help and her continuing support on my journey. Plus, of course, they had a whole great trail magic spread, with hot dogs, snacks, and even Belvita bars! I got a big kick out of that. It was one of the most meaningful instances of trail magic ever.

At the shelter that night, Little Bear was thrilled to run into someone she knew from back in VA, Whitman, and thrilled that he and I were finally meeting. He is my doppelganger. While we didn’t quite “mind meld,” as Little Bear expected, we did get along great! We had a really fun time at the shelter with Whitman, Scram, and a ridgerunner named Samwise.

All this made for one of my favorite days on trail. For once, the trail itself had almost nothing to do with it.

We slept in the shelter that night, which turned out to be a mistake. It was soo buggy, as it had been during the day, and the mosquitos drove me crazy all night. I slept in my bug net and earplugs, but it didn’t entirely fix the problem, and I was hot and sweaty besides. I was all too happy to get out of there early in the morning again.

It was another great morning hiking with Little Bear. We even had a “visitor” and hiked with Scram as well for a while. The trail wasn’t anything to write home about, but we finished the morning on a long (and sorta sketchy) boardwalk.

Little Bear’s mom met up with us in the late morning and took us into Great Barrington, MA. It was a lovely town, and felt gigantic by trail standards. We got sourdough crust pizza from a place that Little Bear had remembered from a previous section hike and had been raving about all weekend. It lived up to the hype!! We also got delicious, rare-flavored ice cream. It was really nice to be included in their mother-daughter time and I was so thankful for their trail magic!

It had begun to rain while we were in town and continued raining as I got back on trail and hiked the rest of that afternoon. It felt hard to hike alone again after being with a good friend for the weekend.

There were plenty more trail friends to be found at Upper Goose Pond Cabin, where I stayed the night. Upper Goose Pond Cabin is an iconic “shelter,” but that word doesn’t do it justice. It’s huge, enclosed, with a nice porch, living room space, and bunks with mattresses and everything. A volunteer caretaker holds down the fort and makes pancakes and coffee for hikers in the morning! The caretaker, Vlobster, turned out to be from Pittsford – another great small-world moment!

The cabin is also on the shores of a great swimming pond. I was sad to get to another good swimming spot at a time of such bad swimming weather. It was an awesome place though, almost certainly the best shelter I’ve stayed in on trail. I didn’t even mind that it was fully half a mile off trail 🙂

Naturally, cool spots like this attract a lot of hikers. I stayed with lots of friends new and old, including Rod, now going by Mutter, who I had last seen way back in Damascus, and the Sun God, who I hadn’t seen since Pearisburg, VA. I was so happy to see him again. I had a really good night there; I like the iconic shelters that bring people together like that.

It rained hard throughout the night. That, plus a real mattress, helped me sleep well, but it was a real morale killer in the morning. I really did not want to hike out of such a cozy place in that rain.

So I didn’t. As the Sun God reminded me, “There are no points for suffering.” Instead, I hung around for a couple hours in the morning. I had chocolate chip pancakes (the chocolate chips were a nice surprise) for breakfast and had a great time chatting with the Sun God and new friends Stakes and Oats. We also helped out by bringing buckets of lake water to the cabin. It felt like we were in the Sorcerer’s Apprentice.

It’s amazing how reinvigorating just a few hours can be. I was feeling so much better by the time I decided to hike out at around 9, and the rain had lightened up significantly, too.

However, even before I rejoined the AT, I was shocked to find the side trail submerged in a knee-deep lake! I couldn’t believe how much rainwater had accumulated overnight. It was helplessly funny, and kinda exciting. There was nothing to do except plunge right through. Even then, I had no idea what I was in for that day.

That morning contained a very special milestone for me, although it probably didn’t hold much significance for most hikers. Longtime fans of the blog will remember that driving under the AT on the Mass Pike was a continual inspiration for me to do this, and that every time I passed it, I’d remind myself that one day I’d cross that bridge on foot. Well, that morning, I crossed that bridge!! I walked over both bridges, actually, that cross the halves of I-90, that I was so familiar with from a different perspective. It was very exciting. A truck even honked its horn for me as I celebrated.

Soon after that momentous occasion, it really started to sink in what I was dealing with. Put simply, it was the worst trail conditions I had ever seen. I’m going to mostly let the pictures and videos speak for themselves here.

The whole trail was ankle-deep water practically all day. Whenever there was a slope to speak of, the trail became a torrent. It made for incredibly slow going splashing through it all. There were unmarked streams every few hundred feet flowing across and flooding the trail, and the marked stream crossings…hoo boy.

Every stream was overflowing, and absolutely gushing. On four occasions, I had to bushwack up and downstream to try to find a safe place to ford. I crossed in a swift and voluminous rush of knee-deep water. It was treacherous and pretty scary at times – easily the hardest crossings I’ve had yet. It was certainly stressful.

It was a unique, interesting, and tough day on the trail. I remained in ok spirits, though the relentless water wore me down somewhat. I was only grateful that the heavy rain didn’t continue while I was hiking!

I stopped for the day at the Cookie Lady (actually the Cookie Lady 2.0) – far short of my original goal, but I was very glad to stop there. Not to be confused with the Southern Cookie Lady in TN, the original Cookie Lady was a woman in MA who would bake thousands of cookies for hikers every year. Apparently, when she sold her property, it was a condition of sale that the new owners continue the practice, and now Ruth and family have taken up the mantle admirably. In addition to cookies, they have homemade lemonade and let hikers camp in their yard.

The Cookie Lady and family have a beautiful property on a blueberry farm. I sat with OG and another hiker, Blink, who was doing a work-for-stay there, eating cookies and drinking delicious hibiscus lemonade. The sun even came out. I was so glad to have such a peaceful evening after a day full of new challenges.

I was fully prepared to set up my tent on assuredly soggy ground, but to my surprise, the family showed me to an old airplane hangar with actual beds for us to sleep in! It was a strange environment, but a most welcome one. Then, the “Cookie Husband” gave us leftovers from their meal for second dinner! It was all lovely trail magic. I slept really well in the hangar that night.

Thankfully, the trail was much improved in the morning. There were no significant fords and far less standing or flowing water in the trail. It had been replaced by more mud, which is possibly more treacherous, but still felt much better. Plus, there were more plank walks to help. It’s amazing what a difference a single day makes.

That afternoon, I got to meet famous trail angel Tom Levardi in Dalton, MA. He has been helping hikers and letting them camp in his yard for over forty years! I really enjoyed visiting with him and having some trail magic he offered me, too.

I loved the spectacular views of Mt. Greylock from Cheshire Cobble at the end of that day. I love the trail! The tiniest little side trails, and spots that no one ever talks about, can hold such remarkable beauty.

I camped that night at Father Tom’s Campsite, a very nice site maintained by volunteers in Cheshire, MA. When I got there, I met yet another local trail angel, Bacon Wrap, and got a bit of trail magic from him.

My cousin Heath made the drive out from Boston to see me that night, and we went out for a late dinner. We had a great time together! I was really glad we were able to make that work. He and his wife had even made me homemade jerky and granola, a delicious special treat for the trail. The trail magic just kept coming, in all forms!

The next day was my last full day in Massachusetts, and it was the most magical of them all. Sort of unusually for a day on the AT, it focused on a single climb: going up and over Mt. Greylock. Mt. Greylock is the tallest point in MA, and the first 3,000-footer on the AT since Shenandoah NP in Virginia. It was a beautiful climb up Greylock, surrounded by mossy conifers (have I mentioned that I love New England?). On the way up the mountain, I got second breakfast from some trail magic that had been left in bags on the side of the trail. This is generally frowned upon, since animals are likely to get in it, so I always have mixed feelings when I see something like that, but of course I’m happy to take advantage of it. If I don’t take it, the critters will, right?

As I neared the summit, who should I run into again but Bacon Wrap! This time he had a full trail magic spread set up, and he made me and OG chicken stir fry for lunch, unusual and refreshing fare for trail magic. I enjoyed a nice break there while we let Bacon Wrap talk our ears off. It was so nice to see him two days in a row and get “repeat offender” trail magic!

The tiny section of trail between there and the summit of Mt. Greylock was the southernmost section of the AT I had hiked before my thru-hike. I had hiked Mt. Greylock with my family in 2021, but we had taken a different route up. This time, I was excited to recognize the trail we had come up that time, and be on that section again.

It was starting to rain when I reached the summit, but I was still able to see some cool views through the fog. I climbed the striking War Memorial, too, which I hadn’t gotten to do before since it was closed back in 2021.

From there, it was just a long, somewhat tough descent down. The rain picked up towards the end, and the trail got quite muddy and slick.

Because of the nature of my day, just climbing up and down one big mountain, it sort of felt like a day hike. Perhaps that’s why I felt kinda lonely that day; usually I have company on day hikes. I got kinda sad during the descent for no obvious reason, and I think that might’ve been it. Whatever it was, though, I needed a pick-me-up. And boy, did I ever get one.

That night, I camped on the lawn of a trail angel named Renee in North Adams, MA. Some trail friends had recommended it to me and spoken very highly of Renee. Immediately, I could see why. It turned out I was the only person that was staying there that night. As soon as I met Renee, she invited me inside and made me cheeseburgers for dinner, along with baked beans and more! It was so kind of her. I had a wonderful time hanging out with Renee and her friend Nancy, another trail angel. They were truly amazing! Renee had a bunch of food that another hiker had left behind, so I partially resupplied from that; then, Nancy gave me a ride to the grocery store to do the rest of my resupply. They were both so, so helpful and friendly! Renee and Nancy are true gifts to the trail community. It was one of the nicest evenings I had on the whole trail, and it came when I really needed it.

Down south in the beginning of my hike, I’d often hear (usually at trail magic) things like “oh, enjoy it while you can, because the trail magic really thins out as you go north,” or “people in New England aren’t nearly as friendly, you won’t find as much trail magic there.” I was proud of my home state for thoroughly proving this wrong. The generosity of the trail community and its wonderful trail angels never ceases to astound me, and this section really hammered it home. Good ol’ New England 🙂