The Ups and Downs of the 5 Boro Bike Tour


I’d been really looking forward to the TD 5 Boro Bike Tour after the pleasant 25-mile training ride I did with my dad, brother, and Todd about a month ago. But as May 1 loomed closer and the forecast predicted rain, I started to feel less confident. I’d never cycled in the rain before. Especially not surrounded by literally thousands of people who might skid and crash into me. But I didn’t want to quit before I even tried (nor did I want to lose the $99 I paid for the event), so Dad went out and bought us all ponchos. On the morning of the bike tour, we tied plastic bags around our socks to try to keep the rain out. Then, in just the barest drizzle, we biked to the subway that would take us downtown.


Todd, Dad, Brother, and me outside of our house before heading to the subway.

Navigating the subway with a bike was a little challenging, but since it was a Sunday the trains weren’t too crowded. And thankfully my brother swapped with me on the stairs: I carried his racing bike and he hefted my regular commuter bike, which is much heavier. We arrived at the starting line around 9 a.m., but had to wait 10 to 15 minutes while the sponsors made speeches and recited to us the rules of the road. The rain had started to pick up by this point, so we just wanted to get moving.

Here’s a quick video of us waiting at the starting line:

Finally the count down began and we were off…walking our bikes for a few blocks until we crossed the officially starting line and the road widened, giving us space to ride. The first few miles felt super easy and really fun despite the rain, and it was such a cool experience to see the same buildings I’ve walked passed hundreds of times from the seat of a bike. It took a little while to get used to all the other riders around me, but we weren’t as cramped as I’d feared. We headed north and entered Central Park around the four-mile mark. I expected from our 10k there that it would be hilly, but it wasn’t actually as bad as I’d thought; what was worse was all the wet, slippery horse manure beneath our tires that was impossible to navigate around.

Here’s a video from Dad’s headcam (which he’d mounted to his bike) as we entered Central Park (I’d like to also note that this is what it felt like wearing glasses the entire ride):

From Central Park we traveled through Harlem and crossed the Madison Avenue Bridge into my home borough, the Bronx. Probably a mile later (or maybe even less), we were already crossing the Third Avenue Bridge back into Manhattan. That marked 10 miles. The wind was no longer at our backs; instead, as we rode south, we headed straight into the wind and rain. And it was hard! Even going downhill, I still had to peddle to keep myself moving forward. When we hit a tunnel, everyone cheered and whooped and made loud sounds that echoed off the walls. You can’t really hear it in the video below, unfortunately, but you’ll still get an idea of what it felt like to get a brief respite from the rain (my brother is in the gray shorts and I’m in the bright blue pants):

We crossed the Queensboro Bridge into Queens and made our way up through Astoria, then back down along the waterfront until we finally came upon a rest stop at mile 25. They had apples and bananas, but they’d run out of energy bars. At that point I felt a little tired, but mostly just damp. My hoodie was soaked through, despite my poncho. The rest stop was crowded and the rain continued to patter down, so we didn’t linger long. Dad, Brother, and Todd all ate bananas. After a quick bathroom break and a few selfies, we rejoined the course.


The massive lines of people waiting for Port A Potties at the rest stop.

At mile 30, I struggled over the Pulaski Bridge connecting Brooklyn to Queens. The others in my group pulled ahead until I lost sight of them, and all I could do was huff and puff and keep moving my legs in hopes of ascending without having to walk. I couldn’t feel my feet; rain had somehow seeped through my plastic bags and into my socks, puddling up around my toes. I pedaled and pedaled and didn’t seem to be going anywhere. But I finally crested over the bridge and cruised down the other side—only to see Dad, Brother, and Todd huddled off to the side of the road. As far as I could tell, the entire derailleur and chain had popped off my brother’s bike. We stood in the rain for a while trying to fix it and scout for help, but eventually Dad and Brother had to leave the course.

Todd and I pushed on, determined to make it to the finish festival in Staten Island. By mile 33, I couldn’t feel my hands, either. My teeth chattered incessantly. We pulled over so I could gulp down some water. We walked our bikes for a few minutes, and I felt scared because I couldn’t even feel myself stepping on my feet—no pins and needles, nothing at all. I broke down in tears. My legs felt fine, but I was just so wet and cold that I could barely function. But with Todd’s encouragement, I got back on my bike and cried and cursed all the way over the bridge and into Staten Island. (Click here to see a funny picture of me, still crying a little, as I crossed the finish line.)

I was too cold to enjoy the vendors or the music at the finish festival. Instead, we raced as fast as we could the last two miles to the ferry. Once inside I collapsed, hungry and tired and freezing and still a little weepy, but also triumphant. The 40-mile bike tour was one of the hardest physical challenges I’ve encountered, but I did it!

Now I’m just keeping my fingers crossed for better weather next year.


Tired and cold on the ferry ride back to Manhattan from Staten Island.

14 thoughts on “The Ups and Downs of the 5 Boro Bike Tour

      • Thanks for asking Chris. I just returned from APF Raw National Powerlifting competition outside of Chicago. I came in first in the deadlift for the 198 lbs. or less and 65 to 69 category. So I’m eligible to again compete in the World Powerfliting competition this coming November. But with that said, I could never ride a bike as far as you did, and in rainy weather to boot.

        • Wow congratulations!! That’s awesome. You will have to give me some weightlifting tips for sure. Hope you are having a great weekend 🙂

          • The best weight lifting tip I can offer is don’t try to hard. I have found that trying to hard to get strong results in getting hurt and weaker.

            A rest day is just as important as a day in the gym. We need both.

            I would only do a single rep perhaps once every three months. Singles are where one gets hurt. You need to do them for contests and to see where you are at, but otherwise avoid. If you can’t lift the weight for 3 reps, it is too heavy for training

            Good luck and be careful

    • If you’ve never been to New York, it’s a great city to visit, and the bike tour was such a fun event. If you’re interested, make sure you keep close watch on when tickets for next year’s event go on sale (probably around next February), because they sell out so fast! I’m actually going to Paris on my honeymoon in August! Have you been there before?

      • No but I was close to it once. What a great place for a honeymoon.
        I really want to explore the states, take a train and maybe find a new place to land.
        I want to see the light houses too!
        Don’t forget to play Power Ball today:)

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