Hiking the Appalachian Trail: Week 9 – Grayson Highlands Ponies & Longhorns

Last updated on December 9th, 2025 at 08:00 am

Thinking about an Appalachian Trail thru-hike? Or maybe you’re just curious what it actually feels like out there on the trail? Either way, you’ve come to the right place!

Hi! I’m Cindy. In 2022, my husband, Barrett, and I completed an Appalachian Trail thru-hike! 🥳

I journaled every day while on trail, and those entries are now being turned into a monthly AT series on this website, available for anyone who may be interested in reading about our AT thru-hike tale!

🔗 Want to start at the beginning with week one? 👉 click here.

🔗 Browse all the weekly trail journals 👉here.

Just know, if you plan to tackle an AT thru-hike, you’ll be in for an incredible adventure!

Also, if you know us as flip-floppers, we don’t know at this point that we will be flip-flop thru-hikers (more on that soon). When we started, we had conducted months of research. We chose to begin our Appalachian Trail hike NOBO, in Georgia, in April.

(We now know that starting as Flip Floppers or in March would have fit us better. But that’s for a later post.)

Just know that when picking a route for the Appalachian Trail, you can always change it up anytime!
👉 Click here for tips on where and when to start an Appalachian Trail Thru Hike. 👈
👉 And click here for advice on thru-hiking backpacking gear. 👈

Alrighty! Welcome back to my Appalachian Trail thru-hike journal series!

Week nine of our Appalachian Trail hike is a mix of magical trail moments (hello, wild ponies 😻), exciting new beginnings for some new pieces of gear, trouble brewing for other gear swap choices (decisions made this week will end up dramatically impacting the next few weeks, and ultimately the entirety, of our hike…), and the mounting pressure of realizing Katahdin is still very, very far away.

If you’re new here, you can start with week one of our Appalachian Trail thru-hike journals here or catch up on past weeks here. Otherwise, let’s dive into week nine on the AT!

Curious what it’s actually like to spend months hiking the Appalachian Trail? Well, here’s week nine of our adventure:

Day 57

May 31, 2022

The first thing I noticed when looking at my pictures from this week was that on this day, at 6:21 am, I was apparently lying in my tent, just casually pricing out 10-day Disney park hopper tickets for two. 😂 Also, it should be noted that I have never gone to Disney for ten days. 😂

I apparently was desperate for a fantasy reward to look forward to in that moment.

Here’s what today’s hike brought us:

We crossed the TN/VA border! 🥳

We hiked into Damascus.

Upon walking into town, we learned that the Dollar General on the main drag was closed because of a broken air conditioner.

So, naturally, instead of resupplying, we went to the Appalachian Heritage Distillery & Brewery across the street, then settled into our fabulous riverside B&B, the Barrett House.

I also saw a baby Killdeer, which made my day, and met yet another trail town cat at our BNB. 😻

✔️ Length: 16.1 AT trail miles
✔️ Total Ascent: 2308′
✔️ Total Descent: 3985′
✔️ Total Grade: 391’/mi

Day 58

June 1, 2022

Today was a zero day, and my Mom drove to Damascus to help us out.

She really saved the day. By showing up and providing a car (and an extra set of hands), she helped us complete our resupply and gear swap errands much more quickly than if we had done them on foot.

Speaking of gear swaps… oof.

We made some gear swaps here that will turn out to be absolute winners, and others that would wind up being complete disasters. Obviously, at the time, we had no clue.

Don’t worry, it won’t take too long to reveal which worked and which didn’t, and the impact those pieces of gear had on our hike.

Part of the gear swap was both of us getting new packs, in the hopes of getting a few pounds off our backs.

I swapped my Osprey Aura pack for a Mariposa 60. Barrett swapped his Gregory Baltoro pack for a Hyperlite Windrider 55L.

While in town, we also had at least three meals at Damascus Diner.

My Mom took off with our old packs at the end of the day.

Because Mom helped us get around and resupply quickly, we didn’t spend our entire zero day walking from errand to errand, which was a true luxury. It also allowed us to spend the evening in the Adirondack chairs by the river. ❤️

✔️ Length: 0 trail miles

Day 59

June 2, 2022

We packed up our new packs after our satisfying Damascus break and headed back out to trail.

I stopped at the gear shop, Damascus Outfitters, on the way out to weigh my new pack. It was 34 pounds fully resupplied.

Then, in a rather wild coincidence, we finally met lady Barrett. We knew there was a woman hiker on trail also named Barrett. What are the odds we’d run into her right after staying at the Barrett House?

We didn’t get as far as we had hoped on this day. A storm rolled in, bringing on-and-off rain, including a rainy night.

We could tell it was about to start pouring, found a spot to set up the tent, and ended up with an incredibly chaotic setup. We were trying to beat the rain but completely failed and ended up soaking the tent during setup. Then it stopped raining almost immediately after. 🤦‍♀️

✔️ Length: 6.7 AT trail miles
✔️ Total Ascent: 1444′
✔️ Total Descent: 1101′
✔️ Total Grade: 382’/mi

Day 60

June 3, 2022

Today was a stunning day… that I barely remember. Do you ever have days where you look back at the photos in your phone and think to yourself, “Wow! That was a shockingly beautiful day! Why don’t I remember it a little better?”

That’s exactly how I felt looking back at this day.

It’s rare for me to look back on a day and wonder if I genuinely appreciated it enough, but looking back on this day, I had one of those moments.

I took almost no notes.

Looking back, I wonder if I was:

• Adjusting to my new pack?
• Still soggy from yesterday?
• Tired?
• Having a bad day?
• Or maybe the day just got missed.

🤷‍♀️ Couldn’t tell ya!

Whatever it was, it was gorgeous!

Here are a bunch of pictures from this lovely day, and the things they made me remember:

I started this day by taking 10 minutes to sit and enjoy my morning coffee down by the river. I remember cherishing this moment. I also remember seeing and hearing river otters while I was down there, and hearing them again throughout the first part of the day’s hike.

We were up and hiking at 9:15 am.

The beginning of the hike on this day intersected with the Virginia Creeper Trail, which is a hiking, biking, and horseback riding trail, so this section was incredibly smooth.

We spent the night camping at an awesome spot between the first- and second-tallest mountains in Virginia (It’s all downhill from here for a while! 😹), and fell asleep after eating dinner and watching the golden sunset while our tent dried out.

✔️ Length: 15.2 AT trail miles
✔️ Total Ascent: 4931′
✔️ Total Descent: 2069′
✔️ Total Grade: 459’/mi

Day 61

June 4, 2022

This was a day I had been dreaming about for weeks: Grayson Highlands pony day! 🐴✨ I woke up ready and excited to see friendly, wild ponies. And wow, did this day deliver! 😻

We started hiking at 9:25 am.

You are about to be flooded with pictures because this day was extremely picturesque, and I had the hardest time whittling down my camera roll!

Pony day was as magical as I believed it would be.

A lot of people ask me, “What are the best sections of the Appalachian Trail?” They are usually looking for day hikes or weekend backpacking trip suggestions. This section is one of the best! I always recommend it to anyone wanting a magical AT day hike or weekend trip. It’s pure joy.

Looking back on the photos from this day filled me with all the happy feels again and made me really want to bring my daughter to this section of the trail.

There were also longhorns in this section:

More ponies:

But between the smiles, I also started noticing something else.

Barrett suddenly had a spring in his step — almost too much spring. He was ready to fly and is becoming physically farther ahead of me in photos than usual. His pack weighed less, and he felt strong.

Meanwhile, mine also weighed less, but I was not feeling as hot. I didn’t know why yet.

Despite Barrett being ready to go, you can see the stress creeping onto his face in the photos — the “Are we going to finish in time?” energy. I mean, is this not the face of a man who wishes I would take fewer pictures and just walk a bit faster? (Each of these photos was taken at two different points in the day, when we came across his favorite flower: Rhododendron. 😆)

I joke, but I can definitely see the “Are we going to make it to Katahdin in time?!” stress starting to take over Barrett in the photos throughout this week. I’m either getting this face a lot, or he’s a little dot, walking pretty far ahead.

The truth in this moment is that Barrett finally got some weight off him. He’s ready to cruise! The same should be true for me, but it’s not for some reason, and I don’t quite know why at this point.

At 6:35 pm, we got to a campground and spent the evening with other thru-hikers and ponies.😻🐴 10/10 recommend.

✔️ Length: 11.6 AT trail miles
✔️ Total Ascent: 1632′
✔️ Total Descent: 2353′
✔️ Total Grade: 343’/mi

Day 62

June 5, 2022

We were hiking from 9:20 am today until early evening.

We saw more ponies on this day’s trek:

And more gorgeous scenery:

And another longhorn:

This is the last of the ponies (the little one napping 😻):

Barrett was CRUISING:

Here’s more gorgeous scenery:

And a deer:

At 7:30 pm, we stopped and set up camp. Barrett made a fire this evening! Which I loved. 😻

I can see the frustration on Barrett’s face and in his posture in photos from this day and a few days earlier. He was stressed.

My notes are sparse during this time, so I’m sure I noticed it then. I was likely trying my hardest to keep things organized and positive, as I tend to do. I’m also fairly certain I was HURTING.

I can tell the tension of “we need to get to Katadhin before the winter cutoff” was weighing heavily on him.

By this point in the trail, it seemed like every day the number of miles we had to hike on all of our future days was slightly ticking up and up.

We both felt the pressure and wanted to move fast. I hated that I felt like I was dragging, for reasons I couldn’t yet identify.

We camped at a pretty, small, wooded stealth site that was perfect for one tent, and appeared at the right place, at the right time. I ate fake tamales out of a bag and watched the campfire burn from my sleeping pad inside the tent until I fell asleep.

✔️ Length: 14 AT miles
✔️ Total Ascent: 2064′
✔️ Total Descent: 3548′
✔️ Total Grade: 402’/mi

Day 63

June 6, 2022

On this day, we were trying our hardest to end in Marion for a resupply. It turned into a long day of steady pushing.

I was hurting. Barrett was determined. The gap between us — both physically and emotionally — kept widening.

At 6:00 pm, we made it to the spot on trail where we could pick up a ride into town, and got to an Econo Lodge for a shower, bed, and sleep. Tomorrow we will resupply.

We ate Mexican food, and I iced my feet like it was my part-time job (because apparently it now was).

A lot of this segment is being remembered via looking back on photos three years later, which isn’t optimal.

However, looking back now, I understand why this part of the trail feels so blurry. I’m reasonably sure it’s because two things are going on during this portion of the trail:

1️⃣: We are kicking up our mileage and putting in long hiking days. I am sleeping as much as possible when not hiking, meaning there’s not much time for journaling.

2️⃣: I am operating under a couple of bad gear choices during this portion of the trail. Choices I won’t fully understand for a few more weeks. And those choices? They would eventually snowball into one of the most challenging phases of our entire hike, really messing with my body and both our heads.

✔️ Length: 16.1 trail miles
✔️ Total Ascent: 3138′
✔️ Total Descent: 2831′
✔️ Total Grade: 371’/mi

Conclusion: Week Nine of our Appalachian Trail Hike

Week nine of our Appalachian Trail hike was quieter in some ways, but beneath the surface, things were bubbling.

This was the week of:
✨ Magical pony encounters
🌧 Frustrating storms
🎒 Gear changes we thought were smart
😬 Stress building
🌄 Breathtaking scenery that deserved more of my attention
🫠 The first hints that something wasn’t quite right with my setup

While week eight was all about endurance, week nine was about a small crack in the foundation starting — tiny enough to ignore at the time, but big enough that future-Cindy can now point to it and say: “This is when things started going south.”

Onward to Week Ten, where those changes begin to reveal themselves even more.