Meet Me in Damascus (Trail Days 2025)

Even before I had finished my 2024 AT hike, S. insisted that we attend Trail Days in Damascus, VA, in 2025. I had chosen not to pause my 2024 thru-hike to attend Trail Days. At the time, I was already north of Damascus by about 150 miles and had somewhat of a schedule I had to keep, though that might have just been an excuse I was using to not have to bother with the logistics of backtracking. For the uninitiated, Trail Days is a huge hiker festival that takes place every year the weekend after Mother’s Day. Thousands of current hikers, past hikers, and hiker wannabes descend on Damascus (known as “Trail Town USA”) to celebrate their love of the trail and meet up again with their hiker friends. The event is sort of a mashup of a conference, a trade show, a reunion, and a little Burning Man thrown in for good measure.

Fortunately for me, S. had plugged herself into the AT hiker community, which allowed us to have a strong connection as I made my way north. She became vested in the progress of the people I met along the way, and she found many other hikers who maintained a strong social media presence, so she was excited about potentially meeting some of them in person. Going to Trail Days was great for both of us. I didn’t always feel that way, though. For many hikers, once they’ve completed the trail, they never want to think about hiking again. For those of you who read the blog, you might remember the idea that hiking is Type 2 fun — perhaps not so great while you’re doing it, but wonderful to look back on. Once I was done with the trail, I thought I was done. Even so, practically the second that S. learned the dates for Trail Days 2025, she booked us an Airbnb right on the main drag. I wasn’t so sure but kept an open mind. Sure enough, once May rolled around, I found myself looking forward to seeing my hiking friends and immersing myself in trail culture once again.

S. and I drove down to Damascus on Thursday, May 15. We lucked out with beautiful weather and made it there in the early afternoon. We were too early to check in, so we took a long walk around all the various spots for Trail Days. Walking around Damascus brought back a range of emotions. Over the past few months, I’ve been thinking about what it would be like to try another AT thru-hike. My thinking shifted from being glad the painful parts were behind me to how to mitigate what I disliked most about the trail to make the hike more enjoyable. I’m thrilled I completed my hike, even though there were several times along the way when I seriously contemplated quitting. As we walked in the park through which the AT passes, my brain was battling an onslaught of conflicting thoughts. 

Vendor row was on the trail through the park, and many people were busy setting up their tents and displays. Just outside of town, past the library and a couple of baseball fields, hikers were descending on Tent City. In several places across town, congregants from One Way Ministries were out in force, inviting everyone who passed by to their famous fried chicken dinner — which was free for anyone who wanted to go, hiker or not. A lot of churches up and down the AT support hikers. I’m not a religious person and have always worried about “the catch” of accepting a church’s generosity. But One Way had earned a reputation for their fried chicken, and eating a meal with them at least once seemed to be part of the “Trail Days experience,” so S. and I decided to give it a shot and got tickets to the 6:30 seating. [Wife note: One Way basically offers hikers everything they could possibly need during Trail Days, including multiple meals and snacks each day, haircuts, showers, laundry services, vet checkups for hikers’ pets, gear repair, basic resupply items, charging stations — all completely free!]

We made our way to Tent City to check it out and get wristbands that would let us in ($20 per person for the full weekend, whether you camp there or not). By the time we walked back to our Airbnb, it was time to check in, so that worked out well. 

A few hours later, we headed to One Way for dinner, and as we arrived to get in line, our current favorite YouTube AT hiker got in line right behind us —  Energizer! [Wife note: We’re in his Trail Days video at 6:01 and 9:01.] He’s doing the trail this year with his son, Duracell, and hiked it once before on his own, in 2022. We watch his videos every day, and it was a wonderful coincidence to run into the two of them on our first night. They were incredibly gracious, and we got to sit with them at dinner. Several times throughout the meal, someone from One Way Ministries would go up on the stage to speak to the crowd, but they never once brought up anything religious. The dinner was a purely generous offer — and delicious! [Wife note: In our excitement to talk with Energizer and Duracell, we both forgot to take any pics of the meal, so here’s an AI interpretation for you. At our dinner, though, there were no random eggs on the table.]

After dinner, S. and I made our way back to the Airbnb, and shortly after, Pathfinder came over for a visit. He’d just gotten to town after driving for 15 hours. The last time I saw Pathfinder was when we shared a tent site on the eve of hiking the Presidential range. I first met him in Tennessee, along with Astronaut, Heavy, and Maple Leaf. Astronaut and Heavy planned to arrive on Friday. As for Maple Leaf, he’d gotten his weekends mixed up and driven to Damascus the previous weekend and wondered where everyone was. Oops. It was great to catch up with Pathfinder and share a few beers on our porch.

On Friday, Trail Days was in full swing, but S. and I took full advantage of having a quiet Airbnb with no pets and slept in. Around noon, we headed over to the famous Damascus Diner for breakfast, only to learn that they’d stopped serving breakfast at 11:30. We’d both wrongly assumed that “diner” equaled “breakfast all day.” The fish sandwich was great, though… S. and I had created a kind of Trail Days bingo card for ourselves, which included doing some anonymous Trail Magic for someone, so we picked up the tab for the hiker sitting next to us. Definite highlight.

After our non-breakfast, we made our way to vendor row again, which was now teeming with hikers. I bumped into Stryder, whom I’d met in Virginia just ahead of the roller coaster and crossed paths with again in Pennsylvania, where we’d camped together and ridden out a significant storm. I also saw Chappie and Banana, whom I met pretty early on in Tennessee.

Shortly after, I saw Astronaut, Heavy, and Pathfinder walking toward me. I’ve stayed in touch with Astronaut since the end of my hike, and it was wonderful to see him in person for the first time since Virginia.

As we were greeting each other, I noticed that Guidebook was standing nearby, but as usual, he didn’t seem to remember me, even though we met multiple times during my thru-hike. I mentioned Guidebook several times in the blog, and the running joke was that he never remembered me, so I guess it was only fitting that he didn’t remember me at Trail Days, either. I think I might have actually been disappointed if he did…

Guidebook (on the right) not remembering me.

Looking wistfully at a still-intact version of his tent…

After perusing all the vendors and buying a couple small pieces of art, S. and I were feeling pretty thirsty, so we made our way to the Appalachian Heritage Distillery & Brewery. We suspected that we’d run into Astronaut, Heavy, and Pathfinder there, and we were right. They were posted up at a table enjoying a great musical performance by two former hikers named Slim Pickins and Ketchup. 

L to R: Patch, Heavy, Pathfinder, Astronaut

“Hiker Trash” by Slim Pickins

After a few rounds and some lively sing-a-longs, we made our way to our Airbnb for some porch time. The guys hit the Dairy King on the way, and when they were heading back, I saw Heavy talking with a couple in front of our rental house. I recognized them as Ranger and Smoke Master. S. knew them from YouTube and was really hoping to get a chance to meet them, so I pointed them out to her. She ran down and invited them to join us on the porch for some beers (from Patch and Decipher, naturally), and they accepted! I think that made S.’s entire Trail Days weekend. [Wife note: We all make a brief appearance in her Trail Days video at 1:11.]

After a while, Pathfinder headed back to Tent City, and Heavy took a quick nap in the Airbnb’s hammock. S. mentioned that the bar nearby, Tipsy Bear, was doing karaoke that night, and Astronaut was totally into that idea, so we made our way over and watched him belt out “Born to Run.” The bonus was witnessing Heavy and Astronaut lip sync just about every song the locals “sung.” It was — let me say — an interesting window into the local singing talent pool. After a bit, we decided to check out Tent City and see what was happening there.

The first part of Tent City is a big, open baseball field with a line of porta-potties along one side and a huge pile of firewood that hikers are welcome to use. The vibe is pretty tame in this area. All the excitement goes on in the woods behind the field. After collecting Pathfinder and cracking open a couple road sodas, we headed into the trees. There were lights strung up all over the place, people wearing glow stick jewelry and costumes, and bonfires everywhere.

We came across Slim Pickins and Ketchup playing music by a bonfire, joined by someone on the bongos, and we stopped there for a bit to hang out.

All of a sudden, a couple came up behind me and S. and asked if we wanted to come to their wedding. The guy handed S. his phone and asked her to record his proposal, and then the “bride” asked me if I could play the “Wedding March” on my phone for them.

I’m not sure how legally binding the ceremony was, but they seemed to be enjoying themselves! We called it a night after that, since I actually had to work the next day. (Cue the sad trombone.)

I spent most of Saturday in a video meeting, but S. went out to check out vendor row some more and attend a presentation on foraging before coming back to the Airbnb for the hiker parade. I was going to have to miss that, too, but S. was ready to take pictures of it for me.

Kevin (not sure if he was a vendor or a hiker)

Tara Dower achieved the fastest known time on the AT in 2024: 2,197.4-miles in 40 days, 18 hours, and 5 minutes

The route went right by our Airbnb, so she could take it all in from the porch. I had a quick break for lunch, but it wasn’t long enough to do much, so I just grabbed a cheeseburger from the gas station next door. Mmmm. Gas station cheeseburger…

Hiker Parade: Rob’s view

My work meeting mercifully ended by 4:30, and it was time to have fun again. Astronaut, Heavy, and Pathfinder came over to hang on our porch some more, which was great.

Ranger, the YouTuber S. is a fan of, made a documentary of her 2023 AT hike and was showing it as part of the Trail Days program, so after a little while, S. and I left the guys on the porch to go watch that. (It’s definitely worth watching.)

After the movie, we went back to Tent City, and this time, we wanted to explore the goings-on deep in the woods. In every direction, there were paths leading to various tent groupings. Some had bonfires, some had pretty elaborate tarp setups, some had grills and full buffets of food, a few had people playing live music, others had DJs, and then, there was the main bonfire.

As we’d been approaching Tent City that night, and when we were walking home the night before, S. and I had kept hearing these loud roars of partying hikers, accompanied by pounding drums, and now we got to see where all the noise was coming from. The gravitational center of Tent City is a huge bonfire surrounded by a massive drum circle and people dancing around the flames. The whole scene was very tribal. None of the people banging on the drums and large, blue plastic barrels could be accused of having any sense of timing or rhythm, but it was still fun to see people losing themselves in the atmosphere. Oddly enough, there were a bunch of local police officers mixed into the crowd, just observing and standing by in case things got out of hand. They didn’t seem to care much about the pervasive cloud of weed smoke we were all walking around in. I had to work again the next day (once again, cue the sad trombone), so S. and I called it a night after about an hour.

While I was in my video meeting on Sunday, S. took care of all the check-out chores. When I was done, we walked around the town a little more and then figured we’d start packing up to head home. We’d gotten separated from the guys the night before in the chaos of Tent City, so we hadn’t been able to say goodbye, but then Astronaut and Heavy knocked on the door as we were getting ready to load up the car. It was great to see them both one last time, and not long after they left, Pathfinder texted to say he was coming over to say goodbye as well.

In the end, we had a very full bingo card by the end of Trail Days.  We reunited with trail friends, met and spent time with our favorite “YouTubers,” enjoyed a free hiker meal from One Way, did some Trail Magic, participated in an impromptu trail wedding, got some local flavor of Damascus via some cringeworthy karaoke (not by Astronaut, of course), and rekindled our love of the trail and the people who make it special. The AT community is a treasure, and it was nice to be reminded to stay plugged into it. See you next year, Damascus…