5 Boro Bike Tour

I thought a lot about how to write this ride report. I almost wrote it as a magazine article and tried to get it published but I decided against it for a few reasons. The first is that I started this blog as a way to share a journey with you. I wanted to take you along from where I started as a writer, cyclist, and man at the beginning of the year to where I end up in December. Leaving out a major point on that journey seemed to be missing the point of the blog. I have done a decent job of letting you in and I want to keep that going. The next reason I decided against writing this as an article is that I would have to focus on some facts of the ride and not how it impacted me. I would have to tell you why it was organized and what it benefited as well as some of the numbers associated with the ride. I really don’t want to do that. The final reason is connected to the previous one. I don’t care. I love that it was a charity ride. I love that the money raised funds inner city bicycle education. I love that I was part of 30,000 other cyclists. I also don’t care because this ride was much more about me and how I got there than what was accomplished. I know that sounds selfish, but from my limited point of view I only know how it impacted me, not how it impacted everyone else.

When I started cycling I heard about the 5 Boro Tour. I still don’t know why they insist on misspelling it, but they do. I heard about the lottery to get in and the amazing ride through the 5 boroughs of New York City. I hear about cycling on closed roads and over iconic bridges and I truly thought that I would never do it. The route is about 40 miles long and to a beginning cyclist, especially an overweight out of shape newbie like I was, it might as well been a trip to the moon. I didn’t even think of going, I just thought it sounded pretty amazing. I did start to increase my mileage and start trying small charity rides, but I never even thought about the tour. A year later a friend mentioned it to me again and I thought I might try to register but the deadline for the lottery passed and I didn’t really mind. I was up being able to ride 25 miles, but never 40. I pushed hard all summer and registered for a metric half century in the fall and amazed myself by finishing it. It was only 35 miles, but it was a start. I also realized that 35 wasn’t that much harder than 25. 40 should be possible.

I spent the winter doing my best to derail myself. II became depressed as my unemployment dragged on and on. I gained back some of the weight I had lost. I became angry at myself for gaining weight and became even more depressed as the holidays came and went without finding a job. I decided it all had to change around Lent. I was inspired by a great friend to use Lent as a 40 day refocusing on fitness. I found a new job. I began to see the light at the end of the tunnel. I decided that I needed something huge to help focus all of this renewed energy and to keep myself moving forward. What better way than to vow to do something I was sure that I couldn’t? It was time to try to ride the 5 Boro Tour.

I started going on the Bike New York (www.bikenewyork.org) website to see how the registration worked. I was excited to see that the lottery system had been replaced by rush registration. I marked the date on my calendar and recruited a friend to ride. He was one of my inspirations to get on the bike and start changing my life. He went through a similar process a few years ago so I knew it could be done. He agreed to ride with me. This was going to happen.

Registration day dawned and we both got in without too much difficulty. My friend even found a great hotel. Everything was set for May 5th. We trained and prepared and met in Manhattan on the 4th. The hotel he found was amazing. It was blocks away from where the ride would begin right in the financial district. It was also right across the street from the Irish Potato Famine Memorial. It is a little Irish hill in the middle of Manhattan. The other side of the hotel looked out onto one of the harbors. It was amazing.

The view from the hotel lobby.

The view from the hotel lobby.


The day before the ride all participants have to go to the Bike Expo New York to pick up their registration packets. The Expo was a mad crush of people and vendors all jammed into Basket Ball City on the East Side. We got there and picked up our packets and checked out some of the vendors. We went to Trek and I was sold on what would become my next bike, a Trek Domane 2.0. I also shopped a little and picked up two new water bottles to celebrate the next day’s ride. The expo was a blast and a great addition to the ride; I just wish I could have had some more money to spend! The vendors offered many great ways to blow through your budget.

After a rough cab ride over to the expo we decided to take a subway train back to the hotel. We quickly learned an important truth for getting around in New York. If you aren’t from New York, ask for help in the subway. It took a while for us to find our way back to the hotel, but it is definitely a memory I will hold onto for a long time. I had a blast riding the trains and listening in on random conversations. We also heard a small jazz band playing on one of the platforms. We finished the night off by eating amazing Italian food in a little restaurant right behind our hotel. As I lay in bed that night I couldn’t help thinking how different life could be. In five months I had lost 35 pounds, found a job, pushed myself to the point where 40 miles was a challenge but not impossible, and I was on the adventure of my cycling life. I wouldn’t say that the 5 Boro Tour changed my life, but it certainly motivated me to get back on track and stay there.

The next day I choked down the leftover food from the night before and got ready to ride. We made our way to the hotel lobby and I was stunned. There were hundreds of cyclists getting ready to ride. Local bike shops had employees helping people check tire pressures and make final adjustments. This was just the first amazing site of the day. We left the hotel and rode towards our starting point. 30,000 cyclists can’t just up and leave as one so the organizers had split the group into three 10,000 rider waves. We thought we were going to be early but 6:00 am had us in the middle of our pack. The view forwards and backwards was more cyclists than I had ever seen in my life. At 7:00 the opening ceremonies started and we were able to see none of it. We could almost hear the speeches but we were too excited to really notice. We waited for something to happen, someone to move, anything to show we were on our way. Slowly the people in front of us edged up a few inches. Then a few feet. Then we started walking. It dawned on me that even a third of the total group couldn’t just ride away. We walked. We went blocks until we saw the starting line. We walked through there. We walked for the next half mile before we could even start to move. Slowly the group loosened up and we were able to peddle. It took almost a mile before we could ride at a pace that allowed me to clip into the peddles.

The view towards the start line.

The view towards the start line.


Soon we were zooming north towards Central Park. It was truly surreal to ride on the streets of Manhattan with no traffic. The only cars we saw were police cars blocking the intersections. We were being watched by police the entire route and there were even a few helicopters. Some were new helicopters, but at least one was the police. We quickly came up to the first rest area and were stunned yet again. There was a huge park full of cyclists. There were hundreds of tables for food and water and more porta-potties than I cared to count. This scene would be repeated at each rest area and a few mini stops along the way. At each mini stop there were bands playing to cheer us on. People came out and watched us ride by in each borough. The thought kept creeping into my head that if the people of New York City, who have seen everything, stop to watch something; it must be special.
Some of the 25,000 riders behind us.

Some of the 25,000 riders behind us.


The surreal nature of the ride almost became ordinary. Almost. Each time you thought that things were starting to be normal you rode through another part of the city that amazed you. We rode south down FDR Drive and over the Queensboro Bridge. From the top of the bridge we could see most of the way north along the length of FDR Drive and it was full of cyclists. Tens of thousands of cyclist.

The highlight of the ride was our trip down the BQE highway and over the Verrazano Narrows Bridge. The climb was brutal but the view of New York Harbor from the top of the bridge was something I will never forget. From there it was a blast of a decent straight down the bridge and off the highway into the finishing festival. There was a ton to do and eat there but we didn’t stay long. We still had the last few miles to ride to get to the Staten Island Ferry and back to the hotel in Manhattan where our cars were waiting.

Stilt walker at the Finish Fest.  She was amazing!

Stilt walker at the Finish Fest. She was amazing!


The ride and weekend have been the highlight of my cycling career. There was no better example of how friendly cyclist are and how much fun it can be to ride than those 40 miles. I cannot recommend this ride enough to anyone that can make the trip. I am planning on going again next year, maybe we can get a bunch of people from the blog to go and meet up the night before. Anyone interested?

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3 Responses to 5 Boro Bike Tour

  1. yceblu says:

    You have the ability to put the reader in your shoes and to see and feel the excitement and wonder that you experienced. Well done.

  2. yceblu ‘s thought echoes my own – your blog is extremely well written, the photos you’ve included are perfect in their number, placement, and composition, and yes, you paint a scene so clear it’s impossible to not be present in the reading, to not picture myself there experiencing the same experience. Also, what amazing personal achievements you accomplished in those 5 months. Five months! We all know how quickly that amount of time goes. Well done on the changes you made. I’m happy for you that things went from the way they were to the way they turned out by the time you pressed this entry.

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