Summer, 2025
My last entry here was a few years ago. But this past weekend was so interesting I feel like I have to write about it. It was my 26th Birthday trip with Mason, Tristan, and Jack - three of my good friends here in New York.
The winter has been long and cold. My 100 square foot room has never felt smaller and I have never wanted to leave somewhere so bad. The beginning of the work week was really tough - I was starting to plan my escape from New York to the west coast. I spent a few days unsuccessfully trying to sublet my room and looking around for places to stay out in Seattle or San Francisco for the summer. But for some reason, I really started to feel more stressed about this than I thought I would be. The idea of leaving this city, which although I think is an overall pretty miserable place, and moving across the country where I know almost nobody and starting a new life was really freaking me out. I spent a few days really anxious, which surprised me because I have done this so many times before. I consider myself pretty good at traveling and meeting people. But at the same time, I moved to this city for a reason: to settle down for a bit and make some friends and community. I’ve done that and I don’t really want to give it up all of a sudden.
Mason, Jack, and Tristan had all committed to coming on a bicycle trip with me in Vermont. The idea was to leave Friday morning, ride a 140 mile loop while camping along the way, and return late Sunday. That was all. I didn’t really think much about where to camp or what to eat, just that we would figure it out along the way.
Friday morning was bright and warm. It was probably the first time I’d worn a t-shirt outside in New York since last fall. Spirits were high as we squeezed our bikes into my 2007 Subaru Forester and headed north.
After the 4 hour drive, grocery shopping, and putting the bikes together, we started riding. Perhaps a bit behind schedule. We pedaled down a path by the river and stopped to chat with a few locals along the way. There were folks walking their dogs and getting a bit of sun after the long winter, smiling and laughing. It all seemed so chipper and welcoming. The friendliness continued through the town of Brattleboro where people would stop their cars to let us pass and wave. “We the people” and “Hands off” signs and rainbow flags were all too common for a small mountain town. Peculiar how if you follow the Appalachian mountain range all the way to North Carolina, where I’m from, it’s more common to find a confederate flag or ‘dont tread on me’. It’s as if the mountains emitted a magnetic pole, something intangible yet undeniably different about either end.
Pretty quickly we left the pavement and started riding on gravel roads. There were lots of steep, challenging hills and thrilling descents. It was great. My bike itself is confidence inspiring. It’s only about a year old, it has some nice brakes, sturdy wheels, and is overall very reliable. Jack, however, bless his heart, brought his town bike, which was in desperate need of some TLC. The frame was sturdy (he just replaced the fork since the last one snapped a few weeks before), but the wheels were corroded beyond repair and his worn down basket was filled to the brim with several dozen pounds of weight. (This is foreshadowing) Despite all this, Jack would blast down descents like a train. No fear, just hurdling his rickety old bike to the bottom. While I was tapping on the brakes, he was pedaling and passing me on the side.
For the first evening, we jutted off into a random plot of woods a little before sunset. It probably would have been a good idea to cover a few more miles, but the crew seemed tired and daylight was waning anyways. That night we cooked some dinner and got to bed early because the plan was to ride hard on Saturday. I chose to pack light instead of pack warm, so it was a bit chilly in my hammock, but not too bad.
On Saturday morning we got straight back on the road and made our way into a small town to refill on food and water before a long stretch of nothing. We grabbed some snacks, coffee, and chatted with the friendly folks behind the counter. We tried to just make it a quick stop, but naturally we mosied around for a bit before continuing on. At this point we were already a bit worried about timing because we had 120 miles to do by the next day and we were not riding very fast. But that was a problem for tomorrow…. until Jack took a bad spill and smashed into the dirt right outside of town. He was in the back of the pack so I didn't see him until a guy on a motorcycle yelled at us to look back. All of his things were strewn over the dirt road. and he was looking pretty scrambled. It turns out his massively loaded front rack had snapped and locked up the front wheel.
Thankfully he walked away with just a few scrapes, but his bike needed some work. We stood around for a while, not sure what to do. It had also started to drizzle and we needed a plan. After some deliberation, we decided that the best thing to do would be to just go get the car and put a pause on the intended route to just go ride some trails for the rest of the weekend.
After helping Jack clean up his things, we walked back to the little town where Tristan and Jack would hang out until Mason and I got back. We walked over to the road, stuck out our thumbs, and were picked up pretty quickly by a guy in a pickup truck. He was a fisherman who lived in Montauk, but had a second home here in Brattleboro. He was a skier, but his wife had some knee surgery, so they were planning on selling the house and getting another one in South Carolina. The ski bum part of their life was over. He also lived in New York City for part of his life, but he hated it and left.
We rode with him for just a few miles, but unfortunately, he wasn’t going the same direction as us, so we hopped out and started looking for a new ride. We stood around for about 20 minutes with our thumbs out, no luck. But then I got a call from Tristan asking where we were because apparently he’d found a ride. Some lady with not much to do was jonesing for some adventure and offered to drive us all the way back to our car. When they arrived, we hopped in and introduced ourselves. This lady, lets call her Sarah, asked us if we wanted to go check out her place of work, a ski resort where she runs the daycare. We obliged, since she said it was only going to be a 15 minute detour. Sarah talked a lot about herself. She was quite the adventurous person, she said. And told us a few of her stories.
The ski resort was nice, but there wasn’t quite the view she promised since it was overcast and foggy. But still she talked and we listened because how else were we going to get back to my car? After almost an hour, we were driving past the spot where Sarah had picked us up in the first place and we were finally en route.
Tristan, Mason and I hopped in my car and drove back to find Jack. He was hanging out with some guys smoking cigarettes. We decided to grab a quick beer and play a game of pool before heading off into the woods again. And then as we were wrapping up and loading our bikes into the car, an older guy came over and offered us a joint. We oblige, as we’re certainly not ones to turn down a gift. At this point the sun had come out and how nice the thought of riding through the woods on a beautiful afternoon with a bit of a buzz. Spirits were high despite our change of plans.
Finally, everyone and everything is in the car and we are driving towards the state park. We’re joking, smiling, and “SCREEEEEEEEEECH”
“That wasn’t my car, was it?”
“Dude, that was absolutely your car…” said Tristan in the passenger seat.
“Shit.”
I pull off on the side of the road and we all hop out. Not a single one of us city boys has any clue what could be wrong. As we stood around feeling helpless, Jack muttered a manifestation.
“It’s about time someone pulled over to help us.” And literally no more than 3 seconds later, a bright orange lifted truck pulls up right behind us. A short, chubby guy with a buzz cut hops out.
“What’d y’all do?” He says sarcastically.
I popped the hood for him and he pretty quickly identified the issue: one of my accessory belts had snapped. All we needed to do was get a new one and we’d be on the way. The good-news-bad-news was that there was an auto supplies store down the road and it was closed, but he knew the owner and could get inside. I could still drive my car, but just not for very long because the battery would run out and I also had no power steering.
Our new friend, John, ran into the store, got the new belt, and then quickly went home to get some tools. While he was gone, Jack found some guy in the store who was a self identified “YouTube mechanic.” He took a look at the engine and made the same assessment as John. And then he offered to let us stay at the fancy hotel across the street with his employee discount. While we appreciated the offer, we were definitely going camping that night.
After replacing my belt, John identified another problem: the belt had apparently snapped because my power steering pump was shot, so that needed to be replaced as well.
I made a few calls to auto-supply stores in the area, but nobody had pumps in stock. They could be delivered the next day, though. I double checked that the pump could definitely be there by the next day, but I still felt skeptical considering the next day was Easter Sunday. John said he would be able to replace the pump if we could get our hands on one.
We still needed a place to sleep that night. So we packed up our bikes and headed into a nearby patch of woods. We set up camp and rode down to a lake to skip some rocks. There was quite a bit of chop, but if you throw a rock parallel to the waves you can get a few skips. The sunset was beautiful but we could see storm clouds on the horizon. It poured throughout the night, but we managed to stay relatively dry playing cards in the cramped tent.
I called the auto-supply store first thing in the morning and just as I suspected, the part had not been delivered. It would be there on TUESDAY. I gave John a ring to see if he had any advice. He did not, but still decided to swing by. I think he was just looking for something to do on Easter Sunday… Away from his family. I’ll also mention that it was my birthday, which sometimes lands on Easter, and this was not how I wanted to spend it. We met up with John by the car. Mason and Tristan decided they had to leave. They both had important things to do the next day in New York and there was only one train going into the city that day, and to catch it, they had to leave immediately. I understood and I was grateful that Jack was willing to stay with me and figure it out.
I called up a few more auto-supply stores and found one an hour away that had the part we needed. The plan then was to call up a tow truck, have them drive us and the car to that store, and attempt to install the part ourselves. John hung out with us until the tow truck arrived. We chatted about politics, he was an avid Trump supporter, but he also talked about his debt and how hard it was to save money. His massive lifted truck was the largest part of his debt, roughly $30k worth, or the better part of a year’s salary. I kept my mouth shut, but that definitely seemed more like a luxury item than a necessity, but what do I know?
Our tow truck had arrived. The driver had a whopping 3 teeth and looked a little rough around the edges, but he was a real nice guy. John and him chatted amicably as he fastened my car to the truck. Jack whispered to me “You’d think they’d known each other their whole lives.” Which was certainly true. But maybe that’s just small town America. Or maybe it's just Vermont.
The auto supply store did indeed have all the parts we needed. I’m so, so grateful that Jack had decided to stay. He whipped out a YouTube video that we started following along with. It was probably 1 pm when we started the project. By about 4 we had started hitting some road blocks. Every once in a while we’d go ask the guy at the counter for some advice, but by the 3rd or 4th time he decided to just come outside and see for himself. He ended up basically doing the whole installation. I offered to pay him some money for the help, but he declined. He was a talker and it was clear he was just happy to have some company.
“This is the most interesting thing that’s happened all day,” he said.
We wrapped up around 6. At this point I hadn’t eaten all day. Sometimes when you gotta get something done you gotta just do it and not think about anything else. So Jack and I hit Taco Bell for my birthday dinner and drove the 3 hours back into the city.
If it wasn’t clear, the reason I found this trip so remarkable was the people. The entire state of Vermont never ceased to give. We encountered countless problems, but each and every time there was someone willing to help.
I'm hoping to retry this route another time. We only did like 20% of it, so there’s plenty of reason to go back. Vermont left a strong impression on me. It is the land of Bernie Sanders and maple syrup afterall.