AT Days 91-100: Connecticut, Massachusetts and Vermont, oh my!

The Skinny:

• Connecticut: blowdowns 🌲
• Massachusetts: more magic than anticipated
• Vermont: a good warm-up for NH 🏔️

---

In the last episode of Fresh in the Woods, Trillian and I took shelter during a freak storm over July 4th, whilst still in New York State. The heatwave that made us take a 'zero' day in Fishkill gave way to rain and the realization that the storm wreaked havoc on the trail: scores of trees were blown down over the trail as we entered the Connecticut portion of the Appalachian Trail...

---

Day 91: Monday, July 6, 2026
— Three Months on Trail —
to Silver Hill Campsite at Mile 1,484.2

Wet morning. Chilly for the first time in ages. Slept in a little bit .. Walked through light to moderate rain all morning.

We stopped for lunch at a shelter and the rain tapered off. Continued through Kent, CT on a brief section of road walking and saw a preppy school called the Kent School. The trail then entered the woods and there were signs depicting one of the school’s traditions, painting the year of the graduating class on some rock face way up. We learned that all the towns down here have been out of power since the powerful storm on Saturday, when Trillian and I watched from the safety of the Shelter.

Lots of ups and downs after lunch–getting tired. We finally made it to a shelter, but it was full and the vibes were weird. We decided to push on, walking a flat path along the Housatonic River. Filled water at a piped spring, then began the last push: 0.8 mile up (pretty steep) to the Silver Hill Campsite–a cute place, but for everything being wet. There was one hiker sleeping under a tent that they didn’t even bother setting up… it looked more like a body bag. There was a pavilion in the middle of the field and we felt no remorse in setting up our tents underneath. We didn’t get any wetter from rain, but nothing dried out through the night. The following morning we’d have to don wet socks and shirts.

---

Day 92: Tuesday, July 7, 2026
To Ed McCabe’s Hostel in Salisbury, CT via Falls Village at Mile 1,500.0

Woke up to rain. Shit. Stayed in bed a little longer, knowing it was probably the wrong thing, but I wasn’t about to get up in this crap. Finally mustered the strength to make coffee and enjoy it in the comfort of my tent. There were lots of earwigs and spiders on the outside of the tent. We were under the Pavilion so we were dry but–depressingly–everything outside the tent (but still under the shelter) got wetter. The irony is that at the end of yesterday’s hiking, my sweat-soaked shirt actually dried out.. how funny that, even though it was hanging on a clothes line, it’s soaked this morning. It was rather painful being chilled and putting on cold socks and shirts.

What really sucked was that we didn’t know if the power would be restored at the hostel we were shooting for that evening. Ergo, we didn’t know if we could expect to do laundry. If we did know, we would have put our dry things on–but since we didn’t, it was yet another day in our cold, nasty wet stuff.

The rain kept up all day and we hiked wet. Wet, wet, wet. PUDs all day: some quite challenging, especially with the rocks being as wet as they were. Our pace was very slow, but we made it.

Towards the afternoon, the destruction from the July 4th storm made going even harder: lots of blowdowns on the trail. Eventually we got down from the hills, and exited to the road where loads of trucks from the power company were stationed to repair the lines impacted by the storm.

The hostel owner recommended a local driver who could shuttle us to Salisbury for the night. Doug promptly collected us in Falls Village, CT and brought us to Ed McCabe’s famous hostel (previously run by his grandmother) where the power had just come back online: a miracle! We were thus able to wash our clothes, dry our shoees, enjoy a shower and a comfortable night’s sleep. Perfect. Thanks to Doug and Ed.

---

Day 93: Wednesday, July 8, 2026
to the Hemlocks Shelter at Mile 1,520.5

Morning at Ed’s: coffee and muffins in his kitchen. An absolutely beautiful day: sunny, blue skies, not too hot. We did a big one, starting with a shuttle ride back to Falls Village, CT with Doug. The devastation from the storm still readily apparent, but we saw loads of utility trucks and efforts to clean up. We were advised that one section of trail was particularly bad, and Doug would give us a free ride to avoid the worst of it: we said we’d consider it. The blowdowns were bad in certain sections, but we managed OK. There was an amazing cascade in Falls Village that we first spied through the trees, then we got a great close-up view.

The blowdowns ceased to hinder us as we hiked up Lion’s Head: the first in a series of mountains that filled the afternoon. Following that was Bear Mountain, the last peak in Connecticut. We descended and followed a river through a gorge in a mystic looking shady gorge. The bugs were awful, but the scene was special. We crossed into Massachusetts!

The remaining peaks were good pushes with rewarding views: Mt. Race and finally Mt. Everett: this last one being a very steep climb, complete with wooden block steps attached to the rock face at points. The grueling climb up Everett took us up 700 feet in 7 tenths of a mile (foreshadowing: once in New Hampshire, this kind of grade would be a piece of cake). The descent was gentler, and we made it to the Hemlock Shelter where we set up tents on a very buggy night and cooked inside, protected from the swarms of mosquitoes.

---

Day 94: Thursday, July 9th, 2026
to Benedict Pond Campsite just off Mile 1,538.9

Gorgeous morning waking up to birdsong and blue sky, and I can see mosquitos on the outside of my tent just waiting for me to open the screen– yuck. Trillian must have gotten up early because she brought my bear canister and coffee maker before announcing she was going to try to get some more sleep: I think it was around 5:30 a.m. I made coffee at around 6 and we got going.

We walked through marshland a swamp in which the mosquitos must have gotten hold of cocaine or something: ludicrous numbers of them coming from all angles. I had been warned about this section: Phil (“True Grit”), the massage therapist from back in Delaware Water Gap mentioned how bad the mosquitoes were when he crossed this area. He was right. Eventually we got to Sheffield, MA and were greeted with signs pointing to Trail Magic a short walk off trail. Comments in FarOut (our navigation app) mentioned it was worth the walk. So we went.

The town of Sheffield has so many volunteers to assist with this trail magic setup that they can run it 6 days a week through the hiker season. Every amenity a hiker could ask for (except beer and a shower, haha!) was under this tent and we were thrilled to enjoy a fun break.

---

Day 95: Friday, July 10th, 2026
to Marsha and Tim’s in Lennox, MA via Jacob’s Ladder Rd. at Mile 1,557.7

Up at 5:30 a.m., coffee on and on the trail by 6:30. Beautiful morning, but buggy, and starting to feel muggy already. Excited about the day in Massachusetts, crossing over the Mass Turnpike, and of course, meeting old friends and seeing the symphony at Tanglewood. Very exciting.

After hiking 15 mi, we got some amazing Trail Magic from “Papa Ruby”, whose daughter “Rubicon” hiked the AT back in 2023. He had a few tents set up, and folding chairs and an amazing spread with beers, sodas, snacks, candy, whoopie pies, electrolytes… the works! Spent a little while there along with some other thru hikers. Continued on our way to Lee, MA, to meet Marsha and head to Lennox.

Marsha was waiting for us with delicious croissants and escorted us to the supermarket to resupply before bringing us to her beautiful home in Lennox. We hadn’t been in touch for years and I was unaware she and Tim had moved to Western MA from Wilmington. Upon arrival she opened her pool for us and Trilly and I jumped right in. They extended wonderful hospitality to us and put us up for the night after feeding us and joining us at the Symphony. We had a great picnic on the lawn at Tanglewood and listened to an all-Tchaikovsky program.

---

Day 96: Saturday, July 11, 2026
to the Cookie Lady’s lawn at Mile 1,567

Morning at Marsha and Tim’s: the comforts of home were so divine that we lingered longer than we might otherwise have done. Coffee and pastries and a relaxed morning with conversation and no big urge to rush out the door. It was marvelously refreshing. Marsha headed out to hike with a friend and Tim eventually escorted us back to trail. Before we could even walk anywhere, we checked in with local trail angels who were handing out cold drinks and brownies at the trailhead! Why not have brownies and iced tea after just having had two breakfasts!?

Trail started flat, but didn’t remain that way. In the end, we camped outside the house of ‘The Cookie Lady’, Ruth, who runs a berry farm and lets hikers camp for nearly nothing outside her house or, if desired, in a converted airplane hangar–how neat!?

Upon arrival, Ruth met us with fresh iced tea and chatted casually with us as we signed her register and relaxed on her porch. She said to help ourselves to fresh berries off the bushes.

---

Day 97: Sunday, July 12, 2026
to Father Tom Campsite at Mile 1,585.6

Up and out at 6:45 a.m. Brisk, but beautiful morning. Pretty easy going with a fun stop atop Warner Hill, where there were loads of blueberry bushes. It was a decent view, and it was fun to pick and munch on berries. I kept hearing some slithering down under the bushes, and eventually we saw there were loads of snakes. Probably not poisonous, but pretty large–milk snakes, I believe. We took a couple pictures and then moved on.

Made it to Dalton, MA where we met the legendary trail angel Tom Levardi outside his home. We filled our water bottles and chatted with him before heading downtown to stop at a sub shop for lunch. We split a veggie sub, potato salad and I had a delicious whoopie pie, with an espresso from next door.

In the final stretch of the day we made it to Cheshire, MA, where the town put a fantastic campsite together, named after a famous priest from the local church who used to host thru-hikers in the parish Hall. So inspired was he, he eventually hiked the whole Appalachian Trail himself. The campsite is now affectionately known as the Father Tom Campsite. It had plenty of open space, fresh water, a porta-potty, picnic tables and even two bikes for hikers to use to get around town. Sweet!

---

Day 98: Monday, July 13, 2026
to TOURISTS hotel in North Adams, MA at Mile 1,600.3

Early morning. Lots of dew on the grass at the Fr. Tom Campsite. Coffee ready by 5:45 a.m. Enjoyed with a blueberry muffin from DD’s that I snagged yesterday.

We hiked up to the top of Mount Greylock: the tallest peak in Massachusetts, at 3,489′. The hike itself wasn’t anything too challenging, but the longer push helped warm up our climbing legs in anticipation of Vermont, New Hampshire and Maine, where the real hills would begin.

We spread out and had a picnic lunch on the summit and I even drifted off for a short nap in the sun. After Mount Greylock, we passed over a couple other peaks including Mount Williams and Mount Prospect before descending into the town of North Adams, MA. We needed to resupply, and I felt like splurging so I booked us into a fun, bougie hotel right off the trail.

---

Day 99: Tuesday, July 14, 2026
to Bennington, Vermont: The Catamount Motel via Route 9 at Mile 1,618.6

The hotel room was too nice to get up and out early. Bathrobes, coffee, a daybed and the cushy surroundings meant we had to rest just a little bit and relax. We did. Made a second pot of coffee. Who’s to say it has to be all hiking and sleeping in cramped shelters and damp tents!? We finally got out just after 9:00 a.m. At reception, the manager, seeing we were hikers, asked how it’s going and how much further we have. After we checked out, she drove us the couple of tenths of a mile to the trailhead!!

Trail was up, up, up: not too grueling, but certainly a slog. This brought us to the Vermont border, where there was a little welcoming reception from fellow hiker “Cobra 37”, and then a bunch of other thru-hikers that we have met recently, who also showed up. There was “Lil Beast”, “Ratatouille” and “Squirreley”. We all spent some time there chatting before Trillian and I pushed on. The day was slated to be close to 90°, but the temperatures started more comfortably. The sun was obscured by strange clouds, giving everything a pinky, orangey hue. It’s almost as if smoke from wildfires has made its way over to Vermont. We’d later find out that that was indeed the case.

Eventually, the temperatures did increase, but certainly the mugginess factor was intense. We stopped for lunch under some high tension wires, where an absolutely fantastic breeze helped us dry out our clothes. We pushed on, and stopped again at a shelter where “Cobra 37” was setting up shop. It was so muggy and buggy–“Ratatouille” was just on his way out, and saying he was going to stay at a motel in Bennington, Vermont. I made a little note of that.

We still had several miles to go, and, given the late start, we’d probably arrive around 8:00 p.m. At around 6:00 p.m., as we were reaching the summit of Harman Hill, drenched in sweat, shooing flies away, I asked Trillian if she would want to stay at that motel? She called, and apparently they were fully booked. Damn. A moment later, they rang her back saying they did have a room! We both got giddy and excited. We decided we’d go for it, especially after the manager said he’d send a Trail Angel to pick us up at the road crossing and bring us in. A bit indulgent, sure, but the air conditioning was going to feel so good, and, well… What the hell!?

---

Day 100: Wednesday, July 15, 2026
to Story Spring Shelter at Mile 1,637.5

Feeling tired. Made coffee … still feeling tired. Had to get up and moving, there was an 8:30 a.m. shuttle back to trail and a big, steep climb waiting to be climbed .. ugh.

The climb up sure was something. It’s good: getting our legs ready for New Hampshire. Truthfully, it wasn’t so bad after the summit of Glastenbury Mountain. Just long. The mugginess let up as the day went on and the breeze even became cool. The smoke from Canadian wildfires, however, has darkened everything and given the forest a strange, muddled hue.

We camped at Story Spring Shelter and will pick up this story in a new, exciting blog post. Stay tuned!

---