Walking from Key West to MA in 109 Days

This morning I made my coffee in the shelter before 5AM and then began getting packed up. The privy was a long side trail away from the shelter. But I was just glad that it existed! The state of New York had hardly any privy’s, so I’m grateful for their glorious return. I’ll definitely be missing the convenience when I get out west.

Views of the sun beginning to rise from in front of the Riga Shelter.

Once I was packed up I set out before 6AM. The Riga Shelter had incredible views right from the shelter. So as I was heading out I could see the sun beginning to come up. The sky was a soft blue with bright golden rays peaking through. Then the day got rolling. It was only about 18 miles to get to the road where you’re able to hitch into Great Barrington. The first few miles of the day were pretty gradual. I was just approaching the climb up Bear Mountain. There are really only 3 climbs today before town. But a couple of them look super steep!

Epic views from on top of the first climb of the day.

Eventually the gradual terrain subsided and the climbing began. It was a pretty rocky climb up to Bear Mountain. But I was pleasantly surprised that it wasn’t wildly steep. The trail just slowly but surely weaved up to the top. I remembered this climb vividly. Up top there is a large pile of stones which is basically an overlook. When I was here last time it was just Sweet Pea and I hiking together. We got up top of Bear Mountain just before the sun set.

Feeling fantastic this morning.

After reaching the top of the climb the real fun began. The descent off of Bear Mountain was ridiculously steep. It was rocky and had some areas that I had to hold onto trees or boulders and shimmy down. I just took my time and tried not to crush my knees too bad. These descents have been knee busters recently. I guess it’s just preparing us for New Hampshire and everything that is to come.

A cute cascading waterfall just off the trail.

It felt like it took ages to get down off of Bear Mountain. But eventually the trail dropped back down and leveled out. Then within the next mile I crossed out of Connecticut and into Massachusetts! The 13th state of the calendar year. It’s hard to wrap my mind around how quickly I got here. On New Year’s Eve of 2024 I flew from Boston, MA to Florida. Then made my way to Key West. Then on January 1st I began hiking north from the keys. After 109 days of walking I have made it back to MA! That truly blows my mind. As of now I’m on pace to finish the US portion of the ECT in the same amount of time that it took me to complete the entire Appalachian Trail in 2023. It’s so funny how things have changed over the last few years. I’ve grown so much as a hiker and a person. So many things that used to scare me or feel daunting back then wouldn’t even have me batting an eye now.

Crossing from Connecticut into Massachusetts!

After crossing into Massachusetts I knew there was another climb coming. I had the vivid memory of starting the state with a climb. But I will say that this next climb was also pretty gradual. The trail weaved through the forest and eventually popped out onto some rocky ledges. The trees opened up to my right and I had stunning views of the valley below. The sky was still bright with the glow of the early morning. I really enjoyed the time spent climbing along those ledges. Once I was up there I just rode along a rocky ridge. There wasn’t too much elevation gain for the next mile or so. Then the trail began to descend once more. I knew that soon enough the last climb of the day would begin. And I also knew that it was going to be the hardest one.

The 13th state of the year!

Even though this next climb was only a half mile or so, I imagine it was about 1,000 feet of gain. I didn’t recall the specifics, but had a strong memory of it being difficult. And boy was it. What I had forgotten was that the climb was pretty much vertical all the way up. The boulders you had to walk up were so steep that wooden steps had been bolted into the rock face. I had to pause super quick at least once or twice along the way up. That climb had my legs burning! But I knew it wasn’t going to last too long.

The trail headed up this rocky ledge for half a mile or so this morning.

I just kept pushing and making my way up to the top. It was a slog, but it only last maybe 15 minutes. Then I finally got up top and began making my way back down. The descent was way less steep, which I was very grateful for. I’d rather get crushed on a climb than a descent. My knees do not love these wildly steep descents.

The sky was bright even well after the sun fully rose.

After a mile or two the trail went by a couple shelters. I remembered staying at the Hemlock Shelter in 2023 with Sweet Pea. This time I just walked on by, heading to town. There were about 4.5 miles of descent before the trail leveled out. A lot of the descent was pretty gradual which I was stoked about. Then there was a half mile or so that was super steep. Once again I had to use my hands to slowly make my way down. That certainly wasn’t a fast section. But it was over quick!

The ole Appalachian Trail! I love the sections of trail that ridge along rocky ridges.

Then the trail finally became more gradual for the rest of the day. There were a couple small hills but nothing major. As I walked through this section I did a little multitasking. I got a new Instagram video up and my daily blog post. Then just listened to music as I made my way out to the road. I’m shocked how quickly this morning has gone by!

This is what I picture when I think of MA and VT along the Appalachian Trail. A mess of roots and rocks.

Before I knew it I was on those last 2 miles making my way to the road. It was so flat and easy, and made for a great way to end the morning. As of now I wasn’t really sure what the plan was for the day. Punisher has a friend, Franny, coming out to meet him in Great Barrington. It sounds like his buddy is going to bring us some resupply items and maybe take us out to lunch. I imagine we’ll probably go in and out of town. But it just depends how quickly we get everything done.

These wooden steps had to be added onto the rock face because it was otherwise dangerously steep. Without them the rock would likely be impossible to climb if it was wet.

When I got out to the road, Punisher was there sitting. I had thought that his buddy was going to meet us around noon. But it looked like he was still an hour out. So we began trying to hitch into town. I expected it to take a while honestly. Last time I was here in ‘23 it was a hard hitch. But this time it was divine! A car drove by us and slowed down. Then it turned around and came back down the road! It was one of those “car guy” cars. I couldn’t tell you what kind it was. But the guy clearly cared alot about it. The guy was super nice and I was so grateful that he came back to get us.

The cutest painted rock that someone left on top of Mount Everett.

The ride into Great Barrington was short and sweet. We got dropped off right in the downtown area which was perfect. With some time to kill we decided to head over to a coffee shop. I wanted to try and charge my devices a bit, as I wasn’t sure what the plan was for the day. If we stay in town then charging isn’t urgent. But if we hike out then I’d love to get my stuff charged a bit.

There was a long stretch of foot bridges leading up to the road into Great Barrington.

Once I got in the coffee shop I plugged things in. Then got an iced dirty chai and a bagel. I got some writing work done while I was there. And exported a couple YouTube videos which I finished. It’s so nice being on top of things like I am. I have a bunch of videos ready to go, which is such a relief.

Punisher’s buddy arrived after about 40 minutes or so. He drove all the way from Boston, which is wild. My family isn’t even going to drive out to MA to visit! It’s 3 hours to get out here and 3 hours to get back. Which is just a wild drive round trip. Maybe when I’m further north some family might come out. The trail in NH is actually closer to where I’m from than the trail in MA is. It’ll just depend how things work out though! This year it will definitely be a bit more difficult to coordinate things like that. Just because time is of the essence this year.

This little guy was hidden just off the trail. I was so glad that I saw him.

After Franny arrived we all grabbed some lunch together. I got a fried cod sandwich with sweet potato fries, and it was so dang good! By the time I was done eating though I had lost a lot of motivation for the day. I was full and ready to relax. But at this point I was getting the feeling that we might just be staying in town tonight.

Because we did 37 miles yesterday it worked out well to do a shorter day today. Even doing 18 miles it still averaged out to be over 27 miles a day for the last 2 days. So we could certainly afford the shorter day. Plus, the next resupply stop is Dalton, MA. But it looks like we’ll be getting there during the middle of the day in 2 days. So it won’t make sense to stop off and charge anything. That means it would actually be a pretty solid choice to charge up to push further past there. I know we’ll be walking through some towns in MA and if the mileage works out we might stop and stay in one of them.

After lunch Franny took us to his truck where he had a ton of resupply goodies for us! It was a crazy amount of stuff. I grabbed chocolate, sour candy, bars, goldfish, wet wipes, and some other goodies. I think it will definitely be enough to get me through to Dalton. I would’ve grabbed even more stuff but I didn’t want to get out of control. While we were there we booked a room at the quality inn for the night. Punisher’s brother actually paid to put us up which was a really cool surprise! Then Franny drove us over there.

It felt so good to just relax for the rest of the day. I’m not wildly tired or anything like that. It’s been 30 days since my last zero day, so a short day sounded wonderful! It honestly doesn’t feel like it’s been that long. We’ve done a good job of throwing a couple shorter days in the mix to mimic a day off. But I think the shortest day we’ve done in the last month was somewhere around 13-16 miles. It’s definitely been a solid and productive month.

Great Barrington!

For the rest of the night I just relaxed and got some work done. I wrote for a long time and got a couple videos finished and uploaded to YouTube. I keep them “private” until I’m ready to post them. That way they are ready to go whenever I’m ready. I spent a couple hours doing all of that. Then it was later in the evening and I started thinking about dinner. There was a Thai place just down the road which sounded great. So I ordered some food and walked down to pick it up. I got a Thai tea and yellow curry with rice. The Thai tea was absolutely perfect.

This yellow curry was absolutely delicious.

Then I brought the food back to the room to eat and lounge. Before I ate I actually sat down and filmed a full length YouTube video. I have had this one idea stewing for a little while and have been meaning to sit down and work it out. It feels good to do that and get my thoughts out I love formulating a new creative idea! Once I wrapped that up I headed back to the room and sat down for dinner. The curry was so unbelievably delicious. I ate every last bite. Then spent the rest of the night doing little bits of writing and video work here and there.

As a side note, I just want to say thank you so much to those of you who have reached out about the loss of my pendant yesterday. I know it might sound silly, but it has weighed heavy on me over the last 24 hours since I lost it. When I talked to my mom on the phone today I felt a bit better about everything. My mom is also an incredibly positive person and is convinced that one of you beautiful humans is going to manage to find it and get it back to me. I’m hopeful too! I’ve actually had a couple people reach out who are local to the area and might try to get out there and search using a medal detector. I think I would cry like a baby if someone managed to find it. It’s one thing to lose some random item or trinket. But the pendant was my late grandmothers and holds a very special place in my heart. Over the last day I’ve reached up to touch it, as I frequently used to do. It hurt my heart to not feel it there along the chain. I’m channeling positive energy though and am not ready to give up hope yet. Anything is possible with such an incredible community of people out there.

My grandmothers pendant. Inside it are flakes of gold from gold panning. I’ve worn this every day for the last 10 years.

If you enjoyed this blog and would like to support my hike by buying me a soda or a snack along the way, there is a “Tip the Author” button below! It links directly to my Venmo. Any and all support is incredibly appreciated!

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.