"Does anyone know a park or a parking lot where the cops won't hassle us?" I asked this of the 25 people who were crammed into the large bedroom. In the main loft space, the tenants were discussing new developments, but it was clear that we couldn't have the show here as planned. We were brainstorming what to do next, and it was a cool moment, where everyone who had gathered to see the show had equal opportunity to offer a solution. I didn't know that area of Boston very well, so I was turning it over to everyone else.

There were just three acts and all were acoustic. I often miss playing in a big, loud band, but at times like this, it would be far harder to create an alternative. Since you can play a guitar and sing just about anywhere, we were considering some wild options. Suddenly, our host Josiah thought of the most obvious option: moving everything to the basement. It was an industrial warehouse, and the enormous basement was directly below a 9-5 business. This was ironic, considering all I wanted when I first tried to book a Boston show was to play in a basement.

The basement was indeed huge. We set up on the far end from some machine that was making way too much noise. During my set, I expressed how pleased I was at the change of plans. I was hoping something would go wrong early so I could get used to the idea that our months of planning really just yielded a suggestion for how to proceed, nothing more. I did not realize, at the time, that very little goes as planned on bike tour.

I took way too long to pack in the morning. Blake had ponied up four panniers for me, and I stared at my stuff and wondered what should and shouldn't come with me. I had overpacked for the past week of van touring with Nakatomi Plaza, and now it was time to make the hard decisions. I eventually just crammed the four bags as full as possible with little regard to organization. We left an hour and a half late, exclusively due to my well-known troubles with getting out the door. The ride was long, tiring, and honestly kind of boring once we hit the four hour mark. Things got much more interesting when it started raining hard, and it began raining even harder when we set up our tents. Setting up tents in the rain is a bummer. Setting up tents in the rain in the dark while already soaking wet just plain sucks. Soon after, I discovered that one of the tents was not waterproof and taking on water at an alarming rate. Blake poked his head into the tent and said, "Not to get too apocalyptic, but if tomorrow is like this, we're going to have to figure something else out." What he meant was that we'd have to get someone to pick us up, take us to New York, and reboot our efforts with better gear. Not exactly what I had in mind when we left Boston that morning.

The next day was dry, but Jon and I learned a new meaning of pain when we met the hills of southeastern Massachusetts. There were a few climbs of 1,000+ feet elevation change. I don't know if you've ever ridden your bike to the top of the Empire State Building, but that would give you a good idea of what I'm talking about. Just after we crossed into Connecticut, we met a dude on a bike who was wearing some pro cycling gear, and he told us that we were about to climb the steepest grade in the state. Now, Connecticut isn't that big, but climbing the steepest grade there is far more intense than the steepest grade in say, Kansas. We said goodbye to the pro dude, then descended a huge hill that ended at the base of the mega-grade hill. I made the rookie mistake of trying to maintain momentum up the hill and I waited to shift gears until after I started climbing. My chain popped off under the tension, and I spun the cranks one revolution before totally losing my balance. I fell elbow-first into the embankment along the road. My elbow left a deep mark in the soft soil, and my eyes widened as I realized the fortuitous nature of my fall. Had I fallen a foot farther up the hill, my elbow would have smashed against some lovely exposed granite. As I remounted my bike, I saw the dude from before bombing down the steep ascent. Here I was, wiping chain grease on my shorts and trying to wrangle my 80-pound bike, and this guy was going up and down the steepest hills in Connecticut for fun. It seemed like he was taunting me. Perhaps he was.

I should pause to explain why these hills were so difficult. I ride my bike about an hour a day at home, and I'm a relatively fit individual overall. But now we were riding for six or seven hours a day, with bikes that have 60-70 extra pounds of gear strapped onto them. That's hard enough to do once. We did it on day 1, woke up at 7 AM the next day, and then did it again. And then again the next day. Blake is experienced in this type of touring, so he climbs the hills with ease, even though he has a trailer with two guitars on it. Jon and I do not do anything with ease these days.

My right knee had already started to hurt a bit, and my left ankle was killing me. By the third day, my ankle was improving, but my knee was getting bad. With every revolution of the pedals, my kneecap slid under the painful ligaments in a very unpleasant way. Between my knee problems and a couple flat tires, we were going slowly. It was starting to get dark, and we still had 13 miles to go. We decided to find a hotel, and managed to pull into one right at dark. With six days to go until New York, I was doubting that I could make it in time for our shows. Blake spent three hours that night with his route-mapping software trying to shave off miles without landing us on dangerous roads or hilly terrain. He wasn't having much luck. We were mostly following the Adventure Cyling maps, which are created by a company that selects the best roads to bike on. The maps took us on a half circle around NYC to enter from the west. I looked over Blake's shoulder and wondered aloud if we could just head straight south and try to find a ferry from Connecticut to Long Island. With two more hours of research and mapping, we had a plan to get to New York with only four more days of riding.

We left in the morning in much higher spirits. My knee still hurt just as much as before, but I felt relief that we had lost two biking days and gained two rest days. The northern Connecticut countryside is beautiful, which was good for me to see. I always thought of Connecticut as a suburban wasteland of sorts, which is particularly hypocritical for me to say. As a Jersey kid, I got quite defensive when people only thought of my state as a garbage heap. The new plan was a good one, and we were all confident that we would make it to New York without an emergency evacuation. That afternoon, we arrived at the campsite early and had our first few hours of relaxation of the tour. Blake's dad met up with us and brought a delicious dinner of lentils and veggies that Blake's mom had cooked up. Blake ate about a dozen vegan cookies, and chatting with someone familiar to us was truly refreshing after days of encounters with strangers. While they each had a beer, I finished the two or three shots of rum that I had left over from the Boston show. Blake and Jon found it hilarious that I carried three swallows of rum over 150 miles. Not only am I the one with all the injuries, but I am also the king of luxury items. It is possible the two are connected.

The next day, the terrain changed significantly. As we neared Bridgeport and the southern border, the tone of the road drastically shifted. The pavement itself became craggy and uneven, and the drivers became far more aggressive and perturbed by our presence. It seems that everyone we meet is excited about what we're doing, unless, or course, we are in their way. Then they are just pissed off at us. And who can blame them? We are biking on roads that were built with the exclusive intent of accommodating cars. It's hard for motorists to embrace us when we are taking up one of their lanes. I get that. But it also belies a very American inability to allow anything interesting to get in the way of routine.

When we boarded the ferry to Port Jefferson, I found a Ms. Pacman arcade game in the main cabin. I boldly claimed I would have the high score by the end of the ride, not realizing that the game was rigged so I started with only two lives and couldn't accrue any more. It was exciting to do something so frivolous and pleasing as playing an arcade game. After four and a half days of pretty serious outdoorsiness, it felt good to eat some ghosts.

We camped that night in an unremarkable county park in Long Island, then continued the next morning towards the south. I had been bellyaching about the execrable bagels we got from a grocery store in Massachusetts, and I was quite pleased to find Seaford Bagels for lunch. I instantly declared it a "diamond in the rough," a phrase that Jon and Blake teased me about for days afterward. They don't really know how rough Long Island is, I guess. It got windy and rainy as we made our way towards Nickerson Beach to camp. This campground seemed even more unremarkable. It was simply a field with a bunch of water and electrical hookups for RV's. It looked like a grassy parking lot for a Nascar event. The Atlantic wind whipped against our tents so hard that we worried the stakes might not hold. At that moment, I wondered where we would be instead had we stuck to the original plan.

We decided to explore a bit, and found a handful of long buildings that each housed several dozen cabanas. Other than Barry Manilow's timeless jam "Copacabana," I had no knowledge of such a thing. (Upon further research, I discovered that "Copacabana" isn't even about a cabana. Go figure.) They were each small rooms with shelves and showers. We found a notice on a few of the doors that said everyone had to clear out all their belongings by the end of Labor Day weekend, which had already passed. Many of the cabana renters had ignored this directive, and we found tons of beach toys and lawn chairs hidden throughout the cabana ghost town. I found a wiffle bat and ball, and we played between the rows of buildings. It felt a bit like we had survived a zombie uprising and we were remembering what fun was like for the first time in weeks.

Jon and I biked into town to get some booze, which seemed like pretty alcoholic behavior considering how dog tired we were. We returned victorious and had a dehydrated food feast at a picnic table amongst the cabanas. Then we moved to the beach, where we told stories and gazed at the dull glow in the west: New York City. We acknowledged the fact that we would not have had this great evening had we stuck to the plan.

The following day, we faced the worst biking conditions thus far. We rode through inner Long Island and Queens, past JFK airport and along boulevards that are reserved for cars going way too fast. I was relieved to enter familiar parts of Brooklyn, where I was confident I could bike without getting becoming a human pancake. As we approached the Williamsburg Bridge to cross into Manhattan, we coasted past a NYC Parks Dept. vehicle. Two men in their 60’s were loading gardening equipment into the hunter green van. One of the men looked at us and asked, "Are you guys going camping?"

"Yeah," Blake said, "we’ve already camped all the way here from Boston."

"Well it’s good to see there are still some free spirits out there," he said. He emphasized each word in a way that only a born-and-raised New Yorker can. Then he pointed at his chest with a gloved hand and said, even more emphatically, "Me? I’ve been stuck in traffic my whole fuckin’ life."

His words bounced around in my head as we ascended the Williamsburg Bridge bike ramp. We continued to the center of the bridge and took pictures of the skyline. I congratulated the three of us on biking from Boston to New York, something I never thought I would do, and we hi-fived heartily. We pedaled onward into Manhattan. Below us, cars were crawling on the bridge, stuck in traffic.