I took part in the TD Five Boro Bike Tour held in New York on May 5, 2024!
The weather that day was far from ideal. At the start, the temperature was just 10°C, with winds around 20 km/h—freezing cold—and heavy gray clouds overhead. Still, considering the forecast had shown a 91% chance of rain up until the day before, it almost felt lucky that it wasn’t pouring from the morning. Even layered in long-sleeve jerseys, the cold was relentless, and I was still shivering despite wearing a rain jacket. Hoping the ride itself would eventually warm me up, I first headed to Battery Park at the southern tip of Manhattan to pick up my rental bike.
As fierce sea winds swept through before sunrise, I couldn’t help wondering whether riding in such miserable conditions would actually be enjoyable. And yet, what followed was four and a half hours of excitement—an unforgettable sightseeing experience unlike any other.
Table of Contents
1. This Is New York! — Streetscapes of the City
2. The History of Harlem
3. Into Brooklyn, the Borough of Art
What instantly swept away my gloomy early-morning mood was one of New York’s greatest charms: its architecture. Towering skyscrapers designed by world-famous architects. Apartment buildings created by unknown designers. Old and new structures standing side by side across every neighborhood. Historic brick buildings lined with stylish steel fire escapes, while street trees, pocket parks, and graffiti bring color and character to the cityscape.
Simply looking around is enough to make you feel: This is New York!
So this time, rather than focusing on the ride itself, I’ll take you on a relaxed, pottering-style tour of the memorable architecture I discovered along the course.
At TD Five Boro Bike Tour, the streets along the course are closed to traffic and transformed into bike-only roads for just one day, allowing riders to safely take in the cityscape as they pedal through the city.
Before coming to New York, I had often heard people say, “Riding through a car-free Manhattan is incredible,” but I never fully understood the appeal. It wasn’t until the event itself that it finally clicked—so this is what everyone meant…!
Heading north toward the start area with the Hudson River on my left, the towering skyline of the World Trade Center soon came into view on the right.
With as many as 32,000 riders taking part, the start was divided into six separate groups. VIPs and media participants rolled out first, while the final group began riding three hours later.
My starting group was the first wave, and the start point was in front of the so-called “Jenga Building,” which features public art by Anish Kapoor—a location previously introduced on this site.
After the start, the route passed through Broadway and Central Park before heading into Harlem. Along the way were countless scenes that felt unmistakably New York!—including views of the Empire State Building—but the dedicated bike lanes were simply too enjoyable to ride, and I completely forgot to stop for photos.
At some point, though, I reminded myself that this was a fun ride, not a race. Even in the freezing cold, I wanted to fully enjoy the scenery, so I slowed my pace and began cruising along more casually. That freedom to ride however you like is one of the best things about a fun ride event.
After passing Central Park, the atmosphere of the streets gradually changed, and I realized I had entered Harlem. Before European settlers arrived, Native Americans had lived in this area since the 1600s. Later, the African American population grew, and Harlem gradually became the neighborhood we know today during the 20th century.
Passing through streets lined with buildings steeped in American history, the route then continued on toward the Bronx.
After crossing the Third Avenue Bridge back into Harlem, I came across what seemed to be a local resident enthusiastically shouting, “Keith Haring!!!” while gesturing directions to passing riders.
He was probably trying to point people toward the mural at Crack Is Wack Playground—the only surviving public mural by Keith Haring. He kept calling out to riders as they passed by. The passion was real.
After returning to Manhattan, the route headed south along the Harlem River, then crossed a bridge over the East River toward Brooklyn.
While riding through Long Island City, I spotted a building with an unmistakably atmospheric presence. It turned out to be The Noguchi Museum, the garden museum dedicated to the late Isamu Noguchi, one of the most celebrated sculptors associated with both Japan and the United States, who spent many years living in New York.
I hurriedly pulled out my iPhone to take a photo—but ended up shooting it slightly crooked…
With about a quarter of the ride remaining, I happened to look up and spot a stained-glass artwork by artist Tom Fruin atop a building near Brooklyn Bridge Park.
After finishing in Staten Island, riders return to Manhattan by ferry—with bicycles welcome on board, of course.
And even after getting off the ferry, the discoveries continued—this time at Union Square on the way back toward central Manhattan.
For me, the true fascination of TD Five Boro Bike Tour turned out to be architectural sightseeing by bike. If there’s a next time, I’d love to do far more research beforehand—but at the same time, New York has a way of turning accidental discoveries into hidden treasures.
Either way, next time I want to bring a proper camera and take the route at a slower pace.
That, perhaps, is where the real joy of a fun ride lies.
🚲 Today’s Ride
Distance: Approx. 64 km (40 miles)
Average Speed: Approx. 14 km/h
A slightly brisk sightseeing pace. If you want to experience New York from a unique, city-wide perspective, FBBT comes highly recommended!
Text_ Mayumi Kamura
Profile
Mayumi Kamura
I’m a Global Ride editor. My expertise lies in visual expressions like design, art, fashion, and more. The COVID-19 pandemic prompted me to focus on my physical and mental health. I started playing tennis and resumed taking contemporary dance lessons. Considering that bicycle-related accessories often boast high design quality, I have a feeling I might become a fan during this experience.
Post Date：2024.05.30
