Three States Left

disclaimer I dropped my phone on the ground and I can no longer use the letter a. So I’m using Siri to type.

Day 55

I want to get to a real Hostel because I needed to wash my clothes. After Maryland there aren’t many hostels near the trail or in general. There was 32 miles away called Mosey’s place, so I made a break for it. 32 miles later I got to the High Point State Park headquarters and Mosey picked me up. When I got to the Hostel I quickly showered and went into town for dinner and ice cream. I was hiking today in New Jersey but the Hostel was in Port Jervis, New York. Have a hamburger, pizza and some ice cream.

Miles: ~32

Mosey’s place

Day 56

I looked at the weather and it there supposed to be a thunderstorm. So wanting to avoid the storm I told Mosie that I would hike 20 miles and try to get back to her hostel to avoid the rain and thunder. She said she would pick me up just before the big stairway to Heaven climb in New Jersey. When I got to High Point shelter the rocks in New Jersey essentially ended. Thank goodness. After hiking the 20 miles through a lot of boardwalk and some state parks hotdog stand waited for me at the parking lot that Mosey said she would pick me up from. I met a southbound thru hiker Who gave me the rundown of what I should expect in the next couple days. Kevin was nice enough to give me five dollars so I can buy a hotdog because the hotdog stand only took cash. Mosie arrived and took me and another hiker back to the Hostel. I gorged on some Chinese takeout and watched a documentary on Netflix and called it a night.

Miles: 20

Moseys place

Day 57

it turned out that there was no storm so when I was dropped off I knew I needed to pull some big miles today to make up for yesterday. Hiking through New Jersey and New York is really cool because there are hotdogs stands and other food vendors near the trail. This means that I don’t have to carry as much food equaling a lighter pack. For lunch I stopped at another hotdog stand and even got some ice cream at a local creamery near Warwick, New York. At this point I was now in New York. After hiking about 28 miles receive some trail magic which inspired me to do an extra three. This required me to go through the infamous lemon squeezer. I had to take off my pack as I squeezed through two rocks created a very narrow passage to walk through. In addition I had to do some climbing which required that I throw my pack above the rocks and then climb. I did this in the evening and without a partner which proved to be pretty difficult as I was here for about half an hour. Anyways I got to the fingerboard shelter by 8 o’clock and shared a nice conversation with some Flip floppers at dinner.

Miles: 31.8

fingerboard shelter

Day 58

it was Fourth of July and I had no plan. I didn’t really mind I figured I can take the day to do some extra miles. I went through two State Parks New York and I could not  believe how busy they were. It was like a zoo. And speaking of zoos after descending bear mountain I had to go through a Trailside Zoo. After experiencing wild animals on the trail it was weird seeing them locked behind the cage. I had seen a Mama Bear in her Cubs a couple days before in New Jersey and seeing black bears at the zoo all discolored and confused was a little heartbreaking. I also felt like such an alien walking through the state parks as I had a big backpack and a head net on as People we’re barbecuing and swimming. I wanted to get to the shelter that was near a beach because I thought I would be able to see fireworks. When I got to the shelter it was nearly empty. Only me and three other hikers were there and I got to witness no fireworks. Additionally the mosquitoes were out so I retreated into my tent very early and called it a day before 9 o’clock.

Miles: 35

Cannopus lake shelter

Day 59

I woke up refreshed and ready to crush more miles. Mosquitoes really bad again so I hide in the bug net for most of the day. The goal today was to get to this road intersection where a deli was nearby. When I got to the road I had already done 25 miles. I hate to the deli and ordered roast beef and corn beef sandwiches. I met up with some other hikers and we sat around and drink sodas together. I was going to call it a day but they said they were hiking another 5 miles so I figured I’d join them at the shelter. The deli would’ve allowed me to camp behind their place which is very appealing because I could’ve had another sandwich for breakfast the next morning. When I got to the shelter another hiker told me about something called the Connecticut challenge. We were at the last shelter before the Connecticut border and the challenge would be to do all 54 miles of Connecticut in one day. This was appealing to me. I was gonna do it. I slept immediately after hearing this.

Miles: ~30

Wiley shelter

Day 60

I work at 3 o’clock and realized that I did not wanna do the Connecticut challenge. my legs were so sore and my muscles were just shot up. I realized I needed to get to a place to rest my legs. I hate 8 miles to a gas station where I met the hikers that I met the day before. We had a nice lunch together and I enjoyed some hummus and carrots. It was nice to have semi real food. At this point I was researching places to stay. The nearest town was Kent Connecticut and I found a bed-and-breakfast that was under the radar. I called the number and they agreed to let me stay tonight. This was the best decision I made. I hate an additional five or 6 miles and I was picked up at the intersection by a lady named Barbie. It turns out that her ancestors had founded the town of Kent and she gave me a whole tour of the little town. part of the trail experience is learning about these towns one passes through. Her house that I was staying in was in the countryside and had a marvelous view of the mountains. It was an old farmhouse passed down from generations and the interior was full of antiques and relics from the past. I can’t say nothing about Barbie and her husband Dan who treated me so well in their home. This might have been the most relaxing day that I had on trail. I had dinner with both Barbie and Dan and I got to share stories of the trail and they told me stories about their lives and the town. I would come back here again anytime and I hope more hikers get to share the same experience. There are some things that Barbie asked that I keep secret because there are some surprises that she likes to give to hikers. So if there are any future hikers  who are passing through Kent please give Barbie and Dan a call and you will not be disappointed.

Miles:  13

Barbie and Dan’s house

Day 61

Dan dropped me off at the trail at 7:30 and I was meeting my friend Alec today at around 11. I was a little upset at Alec because he told me that Connecticut was flat. He could not have been more wrong. Regardless I was looking forward to seeing him and hiking a few miles with him. I met him at a Road he took me to lunch or I took a nice 30 minute break from hiking. After this we hit the trail he joined me for about 5 miles before he turned around. I still had another 15 miles to go. I was trying to make it to Falls Village because there was your again another under the radar stay at another person‘s house. for $20 I was able to spend a night in a cabin in a family‘s backyard. The cabin was just built a couple years ago and it was one of the best nights sleep I ever had. I shared the cabin with another hiker and we split a pizza.

Miles: 26

Jenny‘s cabin

Day 62

I wanted to get out of Connecticut and well into Massachusetts today. That meant yet again another big day. I started the trail before six which helped me get some 3 miles in the morning. I crossed over into Massachusetts before 12 o’clock. Only four more states to go. The goal was to get to great Barrington where I would rest up and prepare to take on Massachusetts. But when I got to great Barrington it was only 4 o’clock and I had already height a good 25 miles. So I figured that I would hike to the next shelter which was about another six or 7 miles away. In hindsight I felt like I should not have done this as it took me a little longer to get to the shelter as there were a few big climbs. Anyway I got to Tom Leonard shelter at around 7 o’clock and was pleased to see a good number of people there as well. Water source was terrible however as it was a quarter mile away downhill. I actually socialized the shelter for a little bit before I decided to go to bed.

Miles: 32

Tom Leonard shelter

Day 63

another big mile day. I wanted to camp at a place called the cookie lady. apparently there’s a lady who lives near the trail who bakes cookies and lets hikers camp in her yard. how could I pass up an opportunity like that? Luckily for me the trail was extremely flat today and I was at the cookie ladies house by 4 o’clock. The cookie lady was not there but there were caretakers. I had some cookies and some hibiscus lemonade which happen to be some of the best lemonade I’ve ever had. What’s the cookies were baked just the way I liked it. I like cookies that are little crunchy. After eating my fair share of cookies and a big dinner I set up my tent on nice flat ground and had a great night of sleep.

Miles: 32

cookie lady house

Day 64

The goal was to get to Mount Greylock. I started early again to make sure I was able to get 27 miles at a reasonable time. I passed through two cities: Dalton and Cheshire. I had a nice breakfast at  Dalton. Stop by cough shop and grab a couple bagels and a breakfast bowl. This meal powered me through two mountains when I was able to get to Greylock by 4 o’clock. I even ran into an overnight backpacker that I met at the Tom Leonard shelter. she had done an out and back a couple days ago and now he found himself at Mount Grey lock looking at someone who he just saw about 60 miles ago. We thought it was pretty funny and very coincidental. After some long days of hiking I decided I’d stay at the Bascom lodge at Mount Greylock. I even had myself a nice three-course meal that they were serving. I had better meals other places but I was very hungry and tired and it tasted really good.

Miles: 27

Bascom lodge

Day 65

The Bascom lodge was nice but there was no laundry and I was running out of food. so I realize I needed to go to Bennington Vermont. I was going to cross the border anyway and I would just need to hike an additional 10 to 12 miles and I would be able to get into town to resupply. When I crossed over into Vermont I was not following the long trail for the next 100 miles. The terrain started to change. I could feel the difficulty increase significantly. More rocks and more mud and some steeper climbs. Luckily beginning of Vermont wasn’t anything too tough and I was able to get to the road at 3:30 where I was picked up by a motel driver. I’ve now resupplied and caught up on some calories and hoping to get through Vermont by the end of the week.

Miles: 24

catamount Motel


is very difficult using the voice to text.

Affiliate Disclosure

This website contains affiliate links, which means The Trek may receive a percentage of any product or service you purchase using the links in the articles or advertisements. The buyer pays the same price as they would otherwise, and your purchase helps to support The Trek's ongoing goal to serve you quality backpacking advice and information. Thanks for your support!

To learn more, please visit the About This Site page.

Comments 3

  • Uncle Don : Jul 12th

    almost there, stay strong and focus on the end goal.

  • Dan : Jul 12th

    Chandler, I just binge read your blog from front to back. Nice work, you have a great perspective. You’re really ripping it out there! Can’t wait for your next update.

  • Kevin Williams : Jul 14th

    CHANDLER – you my friend are killin’ it

    we are so proud of you! i know it’s hard to voice text but your updates keep us all connected. Thank you so much! We love you bro & we are 100% behind you!
    you are doing an amazing job & building memories for a lifetime! – Uncle Kevin


What Do You Think?