Editor M’s laid-back architectural sightseeing ride at Bike New York

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

1. This Is New York! — Streetscapes of the City

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…!

The approximately 64 km route loops through New York, with the atmosphere shifting from one neighborhood to the next—Downtown, Uptown, Brooklyn, and beyond. Riding through each area offers glimpses into the diverse lifestyles and cultures that make up the city.
5:45 a.m. The stacked-block-like skyscraper visible on the left is 56 Leonard Street, designed by Herzog & de Meuron—the architects also known in Japan for the Prada building in Tokyo’s Aoyama district.
After picking up my rental bike, I pedaled toward the start area as a gentle warm-up ride.

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.

Directly ahead on the right is 4 World Trade Center, designed by Fumihiko Maki and completed in 2013. In the background to the left stands 3 World Trade Center, completed in 2018 and designed by the late Richard Rogers, also known for co-designing the Centre Pompidou in France.

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.

All of this detailed navigation—just for the start line!

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.

The “Jenga Building” is actually named 56 Leonard Street. The lower section of the building seen at the far left of the first photo in this column is its entrance area, while above rises a 60-story luxury condominium tower.
Looking up at the “Jenga Building” from the VIP area at the start line.
Visible in the rear left is 30 Park Place by Robert A.M. Stern Architects. The slender 82-story tower houses a five-star Four Seasons Hotel New York Downtown with 189 rooms, along with 157 ultra-luxury condominium residences. It stands as one of the key landmarks among the towers of Lower Manhattan.
On the right is the previously mentioned 3 World Trade Center.

2. The History of Harlem

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.

The Alhambra Ballroom was originally built as a theater in 1905. Legendary artists such as Billie Holiday performed here, and the venue also hosted swing dance competitions. The original building was designed by theater architect John Bailey McElfatrick.
Like many grand theaters and ballrooms of its era, it eventually fell into decline, but reopened in 2003 as an event venue. Today, the third and fourth floors even house a bowling alley.
Adam Clayton Powell Jr. State Office Building is a 19-story office tower and state government building completed in 1973. It was named after Adam Clayton Powell Jr., the first African American congressman elected from New York.
Designed in the Brutalist style by the African American architectural firm Ifill Johnson Hanchard, it is said to be the tallest building in Harlem.
Built in 1913, Hotel Theresa became known for its elegant interiors and A-list guests, including Louis Armstrong and Muhammad Ali.
In 1960, Malcolm X also met with Cuban leader Fidel Castro here. Today, the building has been converted into office space.

Passing through streets lined with buildings steeped in American history, the route then continued on toward the Bronx.

For the event, one side of the highway was completely closed to traffic. Visible ahead is the Harlem area, seen on the return stretch after crossing into 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.

The route crosses its third bridge of the event here: the Queensboro Bridge.
The cityscape seen from the bridge. Across the river stands Ravenswood Generating Station in Queens, surrounded by sprawling residential apartment complexes.

3. Into Brooklyn, the Borough of Art

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…

The building, which had been used as Isamu Noguchi’s studio since the 1960s, was originally converted from an old factory. Long Island City itself was once an industrial area lined with metalworking factories.
In 2019, New York City and Queens jointly contributed $4.5 million toward renovations of The Noguchi Museum, drawing attention locally as recognition of the artist’s significance and the cultural value of the building itself.
Heading south along Kent Avenue in the Williamsburg area. On the left stands a condominium building, while on the right is a residential tower designed by the major New York architectural firm ODA, created with the concept that “most units are corner apartments.”
The firm is known for producing a wide range of highly design-focused commercial and residential architecture throughout New York City.
One of Brooklyn’s most iconic mural works, “Above and Beyond,” is a collaboration between artists Gera Lozano (GERALUZ) and WERC. Supported by a foundation grant, the piece reflects how graffiti and mural art have been embraced by the community and become part of the city’s identity.

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.

This piece is the third work in Tom Fruin’s unique Water Tower series, created using recycled materials such as plexiglass collected by the artist himself. Conceived as an homage to New York’s iconic rooftop water towers, the sculpture can apparently be viewed from scenic spots within Brooklyn Bridge Park.
One of New York’s greatest pleasures is discovering powerful works of art unexpectedly appearing on ordinary building walls and rooftops throughout the city.
Visible on the opposite side of the highway is St. Michael’s Roman Catholic Church, established in 1870.
Looking out over the Bay Ridge area from the Verrazzano-Narrows Bridge just before the finish.

After finishing in Staten Island, riders return to Manhattan by ferry—with bicycles welcome on board, of course.

Although the poor weather throughout the day meant I could only capture rather gloomy photos, being able to experience New York’s rich mix of old and new architectural design while riding through the city made me realize just how incredible the city’s potential truly is.

And even after getting off the ferry, the discoveries continued—this time at Union Square on the way back toward central Manhattan.

The glass-covered building in the center is 15 Union Square West, originally constructed around 1870 as the headquarters of Tiffany & Co.. It underwent a major renovation in the 1950s and was extensively redeveloped again in the 2000s, eventually becoming a luxury apartment residence.
The scale of the renovation is so dramatic that it’s hard to tell whether the building was renovated or rebuilt entirely.

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

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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.