The Kaleidscopic Tour of New York That is the TD Five-Boro Ride

Author: Eric Uhlfelder

26 May 2014, Text and Photography by Eric Uhlfelder

One of New York City’s most extraordinary features is its collage of very different neighborhoods. But rarely can one take in the contrasts between places as you do when peddling along the annual TD Five-Boro Bike Tour.

Starting on a cool early morning on the first Sunday in May, more than 30,000 bikers from all over the world crammed into a few blocks of Lower Manhattan, each waiting the staggered start up Church Street to begin the 42-mile trek around the city. The day’s cloud-filtered sunshine with temperatures that peaked in the 50s made for a perfect ride—something that’s far from given.

As the tour progressed uptown, Sixth Avenue grew as dense with riders as it normally is with traffic on workdays. Passage within the Avenue’s glass and concrete canyons suddenly morphed into a bucolic ride as the tour funneled cyclists into Central Park’s lush green landscape; the city’s street grid exchanged for curved tree-lined drives that wandered up the Park’s eastside and down toward the Park’s northern end before the ride reemerged into the straight rejuvenated blocks of Harlem’s Lenox Avenue.

Central Park

Though New York is a water city surrounded by rivers and abutting the Atlantic Ocean, it’s easy to forget such geography when in the center of Manhattan. But within minutes of leaving Central Park, bikers made the first of several water crossings, passing over the Harlem River and into the South Bronx, weaving in and around highways and industrial neighborhoods.

As with the New York City Marathon, the tour’s stay in the Bronx was brief, returning back to Manhattan, again passing over the Harlem River and onto the first of many car-free highway runs.

Along the Harlem River Drive

Along the Harlem River Drive

Heading south along the Harlem River Drive, the highway is aptly named, the ride then flowed into the FDR Drive, which fronts the city’s East River. Progressing south, riders were met by primal screams emanating from under several covered portions of the Drive over which the Upper East Side of Manhattan has expanded. It’s not clear why cyclists yell when they’re in the tunnel, just that every year it’s assured that they will.

The ride then slowed to a walk for many as the route sharply ascended the 59th Street Bridge. But any temporary frustration from the slowing pace was quickly rewarded with the route’s first skyline views as cyclists reached center span then curved their way down the Queens side of the bridge with Manhattan flush in front.

Up the 59th Street Bridge
Up the 59th Street Bridge…

then down the 59th Street Bridge
…then down the 59th Street Bridge

Once off the bridge, thousands then headed north to Astoria Park–which sits in the shadow of the Robert F. Kennedy Bridge–for a mid-ride break.

The tour then traversed the entire western edge of Long Island [a.k.a. Queens and Brooklyn], over the Maspeth Creek, through Williamsburg and beneath its eponymously-named bridge, passing new East River-front developments that are creating some of the city’s hottest new neighborhoods, then through DUMBO and underneath the arched approaches of the fabled Manhattan and Brooklyn Bridges.

Towards the Williamsburg Bridge
Towards the
Williamsburg Bridge
and out the other side
and out the other side.
Brooklyn Bridge
Brooklyn Bridge

While approaching and passing under three of the city’s large East River bridges provides riders with a clear sense of where they are in the tour and the city, the sequence of these passages are also visually very cool. But the best was yet to come.

Up onto the elevated Brooklyn-Queens Expressway, the ride then tracked along side Lower Manhattan and the Upper New York Harbor, passing the Statue of Liberty as the tour headed south toward the bottom of Brooklyn.

Brooklyn-Queens Expressway

Brooklyn-Queens Expressway

One final rest stop was offered right before the ride’s final assault: the mile-long push up the Verrazano Bridge.

The ocean headwinds were especially hard this year, forcing even some of the most determined riders [including this correspondent] to abashedly dismount and walk a part of the way.

However upon reaching the crest of the bridge, all were rewarded with awesome views—north towards Manhattan, south toward the Atlantic Ocean from which much cooler breezes served to chill even the most overheated cyclists.

But it is the view back towards the city that always provokes, recalling a beautiful sunny Tuesday morning that crashed upon the city. And though a new tower has filled the void, the skyline still doesn’t look right.

A defective view from the Verrazano Bridge … taken several years earlier, circa 2012.

A defective view from the Verrazano Bridge
… taken several years earlier, circa 2012.

Passing the ride’s summit, all smiled in the effortless descent to the ride’s official end at the Staten Island base of the Verrazano. But there was still many more miles to go along a shoreline ride‐‐this time fronting the west side of the harbor‐‐before reaching the Staten Island Ferry and the trip back to Manhattan.

This year the queue for the boat was short and the always festive boat ride to the Battery gave riders a last chance to share memories of the tour as legs and backs started to stiffen—no small concern as many still had miles to go before reaching home and a hot tub. But a small price for what always is a most extraordinary day.

The TD Five-Boro Tour

The TD Five-Boro Tour


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