The Appalachian Trail in Connecticut & Massachusetts

The Appalachian Trail in Connecticut & Massachusetts

Table of Contents

Facts about the Appalachian Trail in Connecticut

  • How many miles of the Appalachian Trail are in Connecticut?: 48.4 miles
  • Elevation Range: 260′-2316′ feet

Facts about the Appalachian Trail in Massachusetts

  • How many miles of the Appalachian Trail are in Massachusetts?: 90.4 miles
  • Elevation Range: 650′-3491′ feet

Sunday, July 18, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 119
Location: Kent, CT
Start/End Time: 8:00/4:30
Weather Conditions: Humid

Appalachian trail in connecticut

It poured and there was thunder and lightning all night. Strangely Vista and I had the shelter all to ourselves. There was a lot of young section hikers in a tent pad and we swore they’d be joining us, but surprisingly didn’t.

About a mile in I saw a sign for an upcoming detour due to a bridge that was out. Apparently, that sign was where the detour started, but it didn’t have any blazes or a detour sign like we have had in the past. I didn’t realize I had missed the “detour” until I reached the bridge.

Luckily, Vista was right behind me and we found a tree downstream to go over. She went over first and walked over it. I was terrified and decided to crawl. I was shaking the whole time but made it.

Right after crossing a country road, there was a big sign that said Welcome to Connecticut! I didn’t think it was this soon. It feels great to be back in New England!

Within minutes of being in Connecticut, there was a sign for Trail Magic! This is exactly what I needed today! A former thru-hiker and his did were cooking up egg sandwiches and they had breakfast beers too. We sat and chatted with them for a while. If reaching a new state didn’t make my day, this definitely did.

There is literally water everywhere! We are walking through creeks and streams because the rocks are covered with water. I know I’m back home in New England too as the water is flowing right down the trail.

As a whole, the terrain was tougher than we thought. I think it’s a combination of more ups and downs along with the access of rain and a bit of mud. The 14-ish miles to town took longer than expected.

Walked the mile into Kent, CT on the road with soaking wet shoes. A hiker we had met earlier said it wouldn’t be too hard to hitchhike into town. Lots of cars passed us, but no one picked us up.

Got to town and went to Kent Pizza Garden. Then things went downhill: The IGA was closed so I couldn’t resupply. Vista called our hotel and we can only do laundry by giving it to someone who works at the hotel, so doing it tonight isn’t possible because the safe we’re done for the night. We figured it would be easiest to Uber to our hotel because it was dinner time, but there weren’t any when we finished our dinner Then Vista went to the gas station to get beer and we couldn’t get any cause they don’t sell it. Instead, she got us Ben and Jerry’s ice cream and Coke.

We were able to get to the hotel by calling a local shuttle driver named Chris. Fortunately, she was able to come to get us, and we found out she is the same woman that gave me the coke at the end of the day yesterday!

Our room key was taped to the outside of our door, and we got in with no problem. The hotel room is weird and tiny. For $155 it was a total rip-off. The bathroom sink wasn’t even in the bathroom, it was in the closet on the other side of the wall from the shower. I was so tired though that I didn’t even take any photos. Neither did Vista.

We showered, ate ice cream, and watched TV. It ended up being a great night.

Monday, July 19, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 120
Location: Stony Brook Campsite
Start/End Time: 12:30/5:45
Weather Conditions: Humid

We got up around 7 to get our laundry done by the owners of the hotel, then went for breakfast. Just down the street was the Cornwall Bridge General Store, so that’s where we went. 

When we arrived we found Slowpoke hanging out on the porch having a snack and using the WiFi. It had been a while since we had both seen her. Since then she decided to end her hike. She’s still out here being part of the community and slackpacking her partner, Slim. We hung out with her for a while on the porch, had breakfast, and chatted with some locals. They also had a pretty great resupply so I stocked up!

Afterward, Slowpoke drove us back to the motel and we found our laundry on one of our beds. Half our stuff wasn’t dry so I brought it back and asked them to finish drying it.

Then we found out that check-out was at 10 am, not 11 like most other places we have stayed. So we frantically got our stuff organized. When our laundry was returned to us it was still a bit wet, but we had to leave so there was nothing we could do about it.

Slowpoke drove us back to Kent (She is a Saint!) where we hung out at the Welcome Center with Potato, a hiker I met on the trail the previous day.

Vista, Slowpoke, and I walked around town going to a few stores. We went to the outfitter to get fuel and bug spray (the mosquitoes are terrible!), then the shoe store for socks for Vista, and finally the pharmacy where I got a ball to roll my feet with, CBD balm to massage into my feet, more Aleve, and Apsercream with lidocaine which is also for my feet.

Soon after Vista friends showed up to get her for a brief getaway from the trail. One of her friends was wearing a sweet black and yellow Hawaiian shirt. I asked Vista if she thought her friend would let me buy it off her because my shirt has a bunch of holes in it. The holes are where the shoulder straps sit so I need something new soon so I don’t get chaffing. 

It was definitely a “hold my beer watch this moment” and I don’t know why Vista said, but she convinced her friend to give it to me! 

Before they left, Vista’s friends gave me a small doll named Polly. Apparently, they’ve been passing Polly back and forth since college. My job is to put her in Vista’s pack the next time I see her.

I walked back to the trail, had a hard time getting into hiking. To boost my morale I stopped at the viewpoint and called my friend Kate. I hadn’t talked to her in a while and she always helps put a smile on my face.

Started listening to the 3rd Bridgerton book, An Offer from a Gentleman. Not sure how I’m feeling about this one yet.

Then I ran into the Roaches; Old Yeller, Linger, and Burn! It was so nice to see them. I can’t remember the last time

I saw them, probably somewhere in Virginia.

Along the Housatonic River, I dealt with a small seam of mosquitoes. When I saw Burn I couldn’t even stop to chat with her for long because they were eating me alive.

Thankfully, when I arrived at the campground for the night the mosquitoes had subsided, and I was able to chat with Potato for a bit.

After I set up my tent I made dinner and called Hoagie. She’s currently in Vermont fighting the mud. Then Upchuck showed up to camp just as the sun was going down. 

Tuesday, July 20, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 121
Location: Belter’s Campsite
Start/End Time: 8:30/6:45
Weather Conditions: Hot and Humid

You know those days when you wake up and just lay in bed for hours because you don’t want to get up? Today started off like that. I was up at 6, but didn’t get out of bed until 7:30 and didn’t start hiking for another hour.

The morning started off super easy with a nice flat couple of miles along the Housatonic River. In a few spots, the trail was flooded because the river was high, but the miles were easy.

Sometimes I think I’m so lucky to have great weather until I start going uphill. Within 5 minutes of going up, I was sweating profusely. It was rocky and I was hating everything. I don’t think morale has ever been lower than when I was doing this uphill.

At a rock, almost to the top, I ran into Zey. I met him briefly early on in the hike, and he was at the campsite last night too. He was having the same issue with motivation and morale today. We walked over to the campsite, which has a fun swing to sit on. We sat and talked about the trail and the difficulties we were both having. It was nice to say it out loud and get it off my chest.

The turning point of my day was the surprise river crossing. I didn’t see any signs, but I guess there was a road walk I could have done as an alternative, but I’m always up for a challenge and probably would have opted for the crossing anyway.

There were 4 of us there, Upchuck, Zey, another hiker I’d never met before, and me. It was nice to have others there just in case. I went out first and made it across safely. It was tough and I almost lost a shoe, but it really boosted my morale. It was the challenge I needed to put me I’m the mindset I was doing new things. 

Throughout the day I continued listening to An Offer from a Gentleman. The main character in this book is a bit of a dick, so I’m not loving it so far.

Mid-afternoon I got to a stream where I stopped to soak my feet. Upchuck and Zey joined me arriving soon after I did. Zey really committed and sat right in the stream.

There was one more climb for the day which wasn’t too bad, but I was still sweating bullets. However, once I was up on a ridge so it wasn’t too bad. The rest of the day was smooth sailing.

Belter’s Campsite, my home for the night, wasn’t anything to write home about. The sites were full or roots so setting up in a good spot was a challenge. I have a root jammed in my back as I write this. I’m not going to sleep very well tonight.

Wednesday, July 21, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 122
Location: Laurel Ridge Campsite
Start/End Time: 7:45/6:45
Weather Conditions: Cool but Humid

When I woke up and started getting ready Zey was walking out of camp. He was up and out nice and early. I slept terribly last night because of that root that was in my back. However, I packed up pretty quickly and was out like a shot.

My morning consisted of some downhill, walking through a field, and some Rod walking. Once I was back on the trail I was along the Housatonic River again. There was a small dip in the trail where there was some high water I had to go through.

I took off my shoes and put on my crocs. Unfortunately, the crocs kept getting stuck in the mud so I had to do it barefoot. Little did I know the water ended up going up to my waist. My shorts were wet for the next few hours. As much as I hate it I’ve gotten used to being wet for long periods of time. However, it is still the worst.

I had some more Rod walking until I got to Great Falls. Normally this waterfall is supposed to be amazing, but with all the rain we’ve been getting it was spectacular! The water was raging and I was frankly a little scared as I walked to the overlook.

I ran into Old Yeller and Linger again as they start their last day of slackpacking. We were all headed up Mount Prospect. About a quarter-mile to the top I saw a bear, my first since Virginia. It heard me coming and I saw its little butt running off into the woods. I made a bunch of noise as I snaked up to the summit, just in case.

As I was descending the mountain I saw the Giant’s Thumb. It’s just a big rock sticking upright out of the ground. When I walked up to it I was immediately reminded of the stones in Outlander. Unfortunately, I was not transported back in time when I touched it.

Soon after I hit the 1,500-mile mark! As I write this (from my end of the day mileage.) I only have 682.3 miles to go. It a crazy thought that in about 7 weeks my adventure will be over.

I had another big uphill before setting up camp for the night in the form of Lion’s Head, followed by Bear Mountain. Right before the climb, I ran into Maple and Syrup and we lead frogged or hiked with each other for the rest of the day. Syrup is so kind and we have amazing conversations, and Maple is the sweetest dog on the AT this year.

Lion’s Head wasn’t too difficult and I reached the top in no time. The view was lovely and I didn’t have to wander too far from the AT, which I loved.

After stopping for a break by a stream with Syrup we continued north to Bear Mountain on the topo map it showed a steep ascent and an even steeper descent. On the way up I ran into 2 SOBOs and asked what my downhill was going to be like. They said it was overhyped and easy. Honestly, they both came off like cocky bastards and were completely wrong. More on that in a minute.

When I reached the top I was rewarded with the best view I’ve seen in weeks! This was exactly what I needed after having low morale yesterday. Syrup and I took a photo together at the summit before heading down.

I learned last year on the Long Trail to never trust a SOBO and so far I’m sticking to that. The descent of Bear Mountain was very steep. Anyone that thinks going down that is easy is either stupid or has a death wish. At one point I took out my bear line and Syrup and I lowered our packs down a particularly steep section. I’ve come this far, and I’m not willing to get hurt. I’d rather take more time getting down.

At the base of the mountain, we were rewarded with Sage’s Ravine. Within 5 minutes of hiking through the ravine, I finally felt like I was in New England. There was moss everywhere, pine needles layered the forest floor, and the cascades of water made everything so peaceful. I was home!

There were several swimming holes, but the water was too cold we didn’t go in. Towards the end of the ravine, I stopped and soaked my feet. Maple and Syrup continued hiking.

After a short soak, I dried my feet and put my shoes back on. .1 miles later I real I had dried my feet in vain as I had to cross the river going through the ravine. It was high and I was lazy. With only 1.4 more miles for the day, I just walked right through the water with my shoes on.

When I arrived at the Laurel Ridge campsite I found Maple and Syrup! She decided not to go any further. So we set up camp and had dinner. It cooled off fast tonight and we needed our down jackets. We had a nice quiet night together chatting and enjoying the peace and quiet of the trail. 

Thursday, July 22, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 123
Location: Great Barrington, MA
Start/End Time: 7:45/3:00
Weather Conditions: Perfect hiking weather

Happy 4 month trail anniversary to me! I can’t believe I’ve been hiking the AT for this long. It seems so short, but so long at the same time.

I actually set an alarm today, because I’m staying in Great Barrington tonight. I texted Sarah’s Mom, Karen about getting picked up at Route 7 around 3 pm, so I need to make sure I’m there in time.

Said goodbye to Maple and Syrup, for now at least. I know I’ll run into them again.

Climbed Mt Race easily with the low temps. I really enjoyed the cliff walk leading to the summit. With the amazing weather, I had perfect views!

Mount Everett was more difficult. Really liked the wooden steps in the side of the rock. Made the uphill easier. I hated the downhill and it took me a long time. For the effort, the views heading over Mt Race were much better.

It was all downhill the rest of the day, which was good but…Worst mosquitoes EVER! For about a mile I was swarmed! The bug net over my head helped, but the bug spray did almost nothing.

Thankfully the mosquitoes stopped just before I got trail magic! A group of churches does trail magic on West Road, which happens 6 days a week. I got 2 burgers and a local beer. Nicest people going! I’d love to be able to work with some local organizations at home to do this next summer.

The last mile to route 7 was muddy and a little flooded. My sneakers got super wet, so I ended up just walking right through the puddles. Hopefully, I can get them to dry overnight.

I arrived at Route 7 around 2:45 and waited for Karen. I was so happy that I got there early so she didn’t have to wait for me.

She took me to the Big Y and I bought WAY too much food. I treated myself to a half-gallon of chocolate milk to drink before getting back on trail tomorrow too. We’ll see if this was a good decision or not. Then we went to a local farm stand to get corn for dinner and bought cinnamon sugar donuts for breakfast to share.

I had a lovely dinner out with Karen and her husband, Fred, on their front porch. Lovely conversation and great company. It was so relaxing swapping stories with them. I feel so lucky that they let me stay at their home.

Took a hot bath before bed and tried to finish my NJ and NY journals, but didn’t. The bed was too comfortable, so I just dozed off.

Friday, July 23, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 124
Location: North Mount Wilcox Shelter
Start/End Time: 10:30/6:45
Weather Conditions: Partly cloudy and humid

I slept in the most comfortable bed ever last night, and while I’m sad that I still woke up at 5:45 in the morning I’m so grateful for that bed. I spent the morning relaxing in bed and uploading videos and photos to Instagram.

When I went downstairs Keenan sun Fred was sitting on the front porch eating breakfast. I joined them and we chatted about our travels. I shared stories from my Kenyan safari and from their trip to Costa Rica.

I wish I wasn’t in a rush to get to Vermont by the end of next week to see Sweet William. Sarah, Karen and Fred’s daughter who is a former co-worker of mine, is coming to visit tonight and it would have been lovely to see her. Sadly, I don’t get to do everything I want on this adventure.

My stomach was doing flips this morning. Not sure if it was because of all the vegetables I ate last night at dinner or the chocolate milk, but I knew it was going to be a long day.

Karen dropped me off at the trail around 10:30 and I was eaten alive by mosquitoes. Going uphill I couldn’t even stop to catch my breath because they would instantly swarm me. It was a living hell.

After unsuccessfully warding off the mosquitoes I arrived at a beautiful viewpoint and met Psyche. I had never met her before and we had a lovely conversation about what it takes to finish the trail. 

Met Upchuck at the Tom Leonard Shelter. He didn’t have a great day yesterday and was contemplating quitting. It was so great to see him back out on the trail.

My stomach was doing flips all day, and at one point I stopped abruptly behind a tree near a dirt road to poop. This is when I had the most awkward pooping experience I’ve ever had on trail.

I went next to the tree and squatted to go to the bathroom. Then a truck went by, and I hid behind the tree. 30 seconds later another truck went by I also heard behind the tree. Then just as I was finishing up one of those little gators went by with three young dudes on it all wearing staff T-shirts. I had behind the tree and close my eyes hoping that none of them saw me. So much for that being a relatively deserted dirt road.

And I’m sure you’ll be surprised that there was more mud throughout the day. I nearly lost a shoe, my legs were covered, and it was generally terrible.

Near one of the muddy areas, there was a very small strain. I was crossing over a wooden plank of a bridge when on my left side I saw some splashing. I turned and swimming away it was the tiniest little river otter. I could not get my phone out fast enough to take a photo but it was so darn cute I wish I had been able to capture it on camera.

Arrived at North Wilcox Shelter to a bunch of tents but everyone in complete silence. I really needed some socializing, but didn’t get any. Not loving this bubble I’m in at the moment.

A minute ago while laying here in my tent in the complete silence that is this sheltered area I farted really loud. I’m surrounded by 4 other tents and all I can think of now is if they know it was me.

Saturday, July 24, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 125
Location: October Mountain Shelter
Start/End Time: 7:45/7:45
Weather Conditions: Sunny

I was the first one out of camp this morning. Plus I did 2.5 miles in the first hour and it felt great!

Mid-morning I stopped next to a stream and Linger went by. The Roaches (Linger, Burn, and Old Yeller) are heading to the Upper Goose Pond Shelter. I saw Streak while on this break too and he’s doing the same.

Then the mud happened.

It was everywhere and unavoidable. I lost count of how many times I nearly lost a shoe and my feet were completely soaked.

All the way up to Tyingham Cobble was muddy. Not sure how a hill can be muddy, but here we are. To top it all off I was pretty disappointed about the view. 

Got to the road and found the Trail Shack which has snacks for sale. I got a coke and freeze pop! Ran into Burn, Kiki, and Puff there and ended up doing the trail detour (because of flooding) with them.

Every uphill was challenging today because the mud happened pretty much the entire day.

I walked over the Mass Pike, which I didn’t expect, on a footbridge and took a break next to a beautiful stream. 

Listened to A Discovery of Witches the entire day because my next Bridgerton book didn’t download the other day while

I was connected to WiFi. I was bummed out to say the least!

I really didn’t want to put up my tent tonight because I was so tired, but when I pulled into the October Mountain Shelter there were 2 women with 7 kids who had taken over the shelter. So my tent went up.

Found a spot to put up my tent, Upchuck arrived at camp. Dinner and bed. Everything hurts, but damn do I feel great about 23 miles!

Sunday, July 25, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 126
Location: Crystal Mountain Campsite
Start/End Time: 8:30/6:30
Weather Conditions: Rain then Sun then more Rain

I hate everything about today. I’m not going to get into too many details because I just want the day to be done.

It wasn’t supposed to rain, but it did. There was mud before it starting raining, but the rain made more mud. I had 12 muddy miles into Dalton, MA and by the time I got there, my legs were covered in mud.

The only good thing about today was the cappuccino crunch ice cream I got at Sweet Pea’s ice cream shop. It definitely wasn’t the mediocre buffalo chicken sub I got at Angelina’s Sun Shop.

After leaving town I walked in the hot sun on a nice even sidewalk and got a slight sunburn.

When I entered the woods after a mile or so there was, you guessed it, more mud. There has been so much mud that I’d like to start a petition to officially change the name of this state to Mudssachusetts. 

I arrived at the campsite and thankfully there was a stream where I washed all the mud off my legs. There were several guys camping at the sight and they had started a campfire. Sadly, within 20 minutes it started to rain again and we were all chased into our tents.

Going up and over Mount Greylock tomorrow and praying that there will be less mud.

Monday, July 26, 2021
Appalachian Trail in Connecticut & Massachusetts Day: 127
Location: Wilbur Clearing Shelter
Start/End Time: 7:45/6:15
Weather Conditions: Sunny with haze

Packing up my tent when it’s wet is the worst. It didn’t rain too much, but it was just enough to make my tent heavier.

Even more Massachusetts Mud today, but thankfully the mosquitoes weren’t as bad

Stopped at Cheshire Cobble view.

Walked through Cheshire. Found out the town gave Thomas Jefferson a giant wheel after cheese after he was elected. Weird.

Just outside of town I laid all my wet stuff out to dry.

Starting hiking up Mount Greylock, but my legs weren’t feeling it today. Took lots of breaks and had plenty of snacks.

Started listening to the next Bridgerton book, Romancing Mister Bridgerton.

Just before the summit, I walked by this little pond with an old cabin on it. In the Harry Potter books, it mentions there’s a Wizard School in Greylock, maybe this is how you get there.

Lots of people on the summit. I didn’t know you could drive all the way to the top. I was sad to find that the tower in the Guthooks map wasn’t a fire tower, but a memorial with windows. The memorial was really beautiful but wasn’t what I was expecting.

I met the very proud elderly mother of thru-hiker, Life Alert. I chatted with him halfway up the memorial for a bit.

Sadly the view wasn’t great because of all the haze from the fires out west.

Met No Name and hiked with her for a bit heading down to the Shelter.

Upchuck came hiking up behind me after that. I hadn’t seen him all day. We hiked for a bit together and chatted about how we think Cheshire should do a Drunk History about the Big Cheshire Cheese.

Arrived at the shelter. Set up tent. Ate and chatted with Upchuck and No Name.

Vermont tomorrow!

Continue reading about my journey along the Appalachian Trail in Vermont!

All my Appalachian Trail Journals

Love it? Pin it!

Leave a Comment