About the Author, Leah LaRocco: “Hi there, I’m a Long Islander who lives in Franklin, Tennessee. My first love was the ocean, but growing up camping and hiking around Vermont also contributed to a deep appreciation for the mountains. Public lands are some of my favorite places to hike and Great Smoky Mountains National Park is a regular weekend getaway. I work full time, but believe dreams and passions can and should be pursued outside of the everyday 9-5. As a naturalist, I hope to convey how incredibly healing the woods, water, and wildlife can be when we make the choice to step outside.” Find her via her Instagram, Facebook, Twitter, and Website.
Click on Leah’s name above to read more about her adventures!
Day 7: Hemlocks Shelter to Great Barrington, MA, 8.9 miles
I am so exhausted. Like hit a wall exhausted even though I’m really enjoying being out here. Right now I’m in my puffy jacket and rain skirt with a pile of laundry next to me, waiting for the washer to open up so I can clean my clothes. It’s 6:49 pm, which means I should be in bed in like 10 mins.
Last night I got to the Hemlocks Shelter near Guilder Pond and was the only one there. It was getting dark when another SOBO hiker named Loner arrived. He’s a retiree who has decades of backpacking experience, and was a delight to chat with. Another hiker came in and camped so we had two bunks to ourselves and I passed out.
It’s odd in a shelter because you hear EVERY single sound. Every breath, every time someone turns over on their squeaky sleeping pad, every slight movement in a sleeping bag, every snore, fart, belch…all of it. Ear plugs help a lot. I always thought it would be weird to sleep with strangers, but it’s not out on the trail, plus no one’s a stranger out here.
When I got up and out this morning, all I could think about was town. I passed some more lovely views where the clouds still hung low below the peaks. Greylock could be seen st adding prominently in the distance. I use an app called Peak Finder to see what I’m looking at. You hold your phone up to a scene and it shows the names of the mountains in the distance.

The trail was downhill and then mostly flat today so I hightailed it as quickly as I could. Pine needles provided a soft bed of trail to walk on, and there were boards hovered precariously over boggy areas. I love walking through the farmlands as well. Today I saw some cows, sheep, and a tempting apple tree that was in the middle of some high weeds. The craving for fruit out here is real!
A woman I met during my naturalist classes at the Great Smoky Mountains Institute at Tremont lives nearby and graciously offered to pick me up and bring me into town. Julia was as angelic a trail angel as ever there was today. I can’t even describe the amount of gratitude in my heart for people who assist hikers on this journey. We had lunch, caught up on life, and then went on a search for bug spray and a legit outfitter in town. In spite of all the resources here, there was none to be found. Great Barrington is the largest town that’s close to the trail in MA, so I expected it to have more. Sawyer Picaridin big spray does not exist here, so if you need that or any specific food items, it’s best to mail them to yourself.
My husband was able to put some things together for me at home and throw them in the mail so I can send my lousy heavyweight bear bag home. I hate the Ursack with a passion. It’s a $90 bulky stuff sack that is bear proof and weighs half a pound. I haven’t needed it at all, so I’m going to use my clothing bag until I get my legit stuff sack in the mail in Dalton. Another thing to note is that the USPS will only ship liquids ground, so if you send bug spray to yourself, it’ll need to go via UPS.

As far as food shopping, I don’t eat most red meat or seafood, so I was looking for plain packaged chicken in a foil packet and the stores didn’t have this. I was also looking for small cans of Frito-Lay bean dip, also not available. I’m still trying to figure out how to add more protein to what I’m eating and it’s been tricky. I managed to finagle some things together for the next three and a half days until I get to Dalton. The Dollar Tree was actually an awesome resupply spot, so I would suggest going there first before hitting up the Price Chopper. They had bags of freeze dried fruit there and the main staples. The food bag feels so heavy, so I’ll be figuring out what weighs the most and eating that first. I was literally looking at snack cakes and figuring out which ones weighed less!
The knee is just not getting any better. I’m pushing through, but it’s also eating away at me a little. Tomorrow I’m planning to do around 13.5 miles and I can’t even think about how it’ll feel. Tonight I was able to go to the Berkshire Community Center and soak in a hot tub for a half hour. It felt so nice. The hotel also has ice so I’ll do that too. All the towns have hiker rates, reduced prices, which is so awesome. The hotels, some of the restaurants, and the community center too.

I know I should probably take a look at work email even though I’m on leave, but my body is so so so tired right now. I can’t make myself do it. Town chores take up every available minute. It’s peaceful being out here, but relaxing, it is not…in the best way possible.
Day 8: Zero in Great Barrington, Mass
I woke up this morning and felt utterly exhausted. The past 7 days have caught up to me. I could have pushed it and headed out, but I decided to honor my body and take a rest day. This isn’t ideal because I am a go go go type of person, but if I can get to feeling better, I know the miles will come easier.
A short walk to McDonalds for a breakfast sandwich confirmed I’m doing the right thing. The knee was hurting right off the bat, so today’s agenda includes drinking a lot of water, stretching, foam rolling, eating nutritious food, elevating the knee, sleeping, and possibly another soak at the community center. The chores were taken care of yesterday, laundry and resupply, so today will be much more chill. I’m still early on in this journey and don’t want to flame out at the beginning. At this point I know I can’t physically do the miles I’d originally hoped, but I want to stay out here and soak up as much beauty as possible. So if that means resting more often, then that’s what needs to happen.
Perhaps one of the lessons I need to learn on this section is how to slow down. I really suck at this. My calendar is always full and I worry a lot about wasting time. Having friends pass away over the years has instilled this intense desire to not take a single day for granted. So I fill the empty moments and plan things in hopes that when my time is up, I can look back and feel like I lived.

Sara Bareilles has a song called Chasing The Sun that talks about the huge cemetery in the center of Queens. Whenever I’ve driven past, I’m struck by the millions of graves, all the lives gathered in that place. There’s a line in the song that says, “All we can do is try and live like we’re still alive.” Every time I hear that line it blows me away. How many of us choose not to live? It’s easy to waste away in front of a TV screen, to become so absorbed by the cities we reside in that we completely lose connection with the land we originate from. “From dust we came, and to dust we shall return.”
Hiking has enabled me to reclaim a connection with the land, to feel part of nature. As I walk through the woods and see bears and frogs and salamanders, I realize that I too am wildlife. My needs are the same as theirs, food, shelter, water. When Cheryl Strayed signed my copy of Wild, she wrote “Leah, Trust your wild heart.” And, my God, I want my heart to stay wild in every sense. Let this world never tame me.
Mary Oliver knew. She walked the woods, quietly, alone, listening not only to the birds and the wind and the river. “Tell me what it is you plan to do with your one wild and precious life.” She gave herself to nature and lived a private life because the heart can be more easily listened to when it is not drowned out by the noise of city traffic and corporate churning.

The word “wild” is defined as a negative descriptor. But for me, it means to be free, unencumbered, to run with hair flowing in the wind, to traverse mountains, embrace what has always lived inside the heart, and to become air, wind, water, land, and spirit.
Helpful Tips: Great Barrington, MA
- Travelodge is centrally located near a Price Chopper, Dollar Tree, South Berkshire Community Center, and restaurants. Laundry is $5. Hiker rate if asked.
- Would suggest going to Dollar Tree to resupply before hitting Price Chopper because they have some of the same things, plus freeze dried fruit!
- The Aegean Breeze Greek restaurant across the street from Travelodge is excellent!
- The Book Loft is a delightful bookstore to spend some time in and feel human again, next to Price Chopper.
- They do not sell Smart Water bottles in this town because they are single use plastic. However, you can buy a container of bleach at the Dollar Tree to clean everything out.
- There is no outfitter in this town. If you need any gear or Sawyer Picaridin bug spray, be sure to mail it to yourself.
- The community center is behind the Travelodge. There is a day use rate of $7 if you tell them you’re a hiker, which includes use of the pool and hot tub. A towel is $1 extra, so borrow one from the hotel.