Five Boro Bike Tour: Wonderful way to explore New York City

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Disclosure: I participated in the Five Boro Bike Tour as a guest of the ride’s organizers, Bike New York, which neither reviewed nor approved this post.

Ever seen an ad for a cycling event—a long one-day ride, a weekend event, a week-long bicycle tour—and thought, “I’m not exactly Tour de France material, so that’s not for me”? I wondered the same thing when I first heard about the Five Boro Bike Tour in New York City.

Sure, I’d done a bit of long-distance riding in the past—the distant past. I’d done a 75K fundraising ride in my 20s, for instance. I’d done a four-day ride across P.E.I. in my 30s.

I’m not in my 20s any more. Or my 30s. Or my 40s, for that matter.

However, I was intrigued by the Five Boro Bike Tour. As the name implies, it takes riders through all five boroughs of New York City (although, in some cases, you just deke quickly into a borough before heading out again). And because it involves some 40,000 riders, whole freeways are closed to car traffic as the tour rolls by, giving riders a rare chance to see NYC in a new way. Also, it’s not a race; riders go at their own pace, and everyone from kids to seniors takes part. And it takes place in May, which is a pretty nice time to visit the Big Apple.

But—and this is a big but—it is 64 kilometres (40 miles) long. That’s roughly equivalent to a round trip from Parliament Hill to Stittsville, Manotick or Cumberland.

Could I do it?

The only way to find out was to follow Nike’s advice and just do it. So I signed up. And immediately panicked.

A winter of training

The thought of cycling for five hours straight certainly spurred me to go to the gym throughout the winter. I’m sure the experts would advise anyone considering a long ride to follow a carefully constructed training program. It probably would have helped. However, I did my usual haphazard mix of yoga classes, Zumba, elliptical workouts and recumbent bike sessions, with lots of long Sunday walks with a friend thrown in. (When the weather was frosty, we went to the Louis Riel Dome in Blackburn Hamlet and walked the track for an hour or so.) I might not have been ready for the Olympics, but I felt reasonably confident.

Next, came the question of what to ride and how to get it there.

Driving to New York City

One of the most popular posts on this site is my post Five ways to get to New York City from Ottawa. If you’ve read it, you’ll know that the very last method I suggest involves driving your car right into Manhattan. So I thought about renting a bike, but I left it too late; every rental bike in the greater NYC area was spoken for, or outrageously expensive, by the time I got my act together. Besides, the last time I did a long ride on a rental bike (the aforementioned P.E.I. trip), I’d regretted every painful, ill-fitting kilometre. A couple of years ago, I’d splurged on a touring bike that I really love. So, I decided, I had to find a way to get it to New York with me.

The Five Boro Bike Tour people have lots of tips about bringing your bike on various forms of public transit. And I seriously thought about parking my car at a commuter rail station and taking my bike on the train to Penn Station. But then I thought about lugging it up various narrow, crowded staircases, while also trying to juggle my luggage. I concluded that I would be in grievous pain before I even got to the starting line. There was nothing for it. I would have to drive.

Long story short: Driving right into Manhattan wasn’t nearly as horrific as I had feared. Because traffic is so heavy, it doesn’t move quickly, giving tourists like me lots of time to switch lanes and navigate. The talking GPS on my iPhone was a godsend. And I picked a hotel that actually had affordable valet parking (sadly, it closed permanently a few months afterwards—perhaps that parking was too affordable).

The very nice doorman helped me wrestle my bike and my luggage into the elevator, and soon I was ensconced and waiting for my sisters, who were arriving by plane from Toronto for a girls’ weekend and to cheer me on. Their plane was late, but eventually we all convened and had a great time. We caught Come From Away on Broadway and did touristy things on Saturday, but I called it an early night because I had to be at the starting line, with my bike, at the unholy hour of 7am.

Getting to the Five Boro Bike Tour starting point

Getting to the starting line in lower Manhattan was relatively easy. NYC subways allow cyclists to bring their bikes on board that day, and at the crack of dawn, even those notoriously crowded trains were pretty empty.

Once I popped out of the station, I just had to follow the clots of cyclists wearing Five Boro Bike Tour bibs to the starting point. Then we waited in anticipation as music thumped from huge loudspeakers. (I suspect residents of this neighbourhood are less enthralled with the event than the participants are.)

We took selfies. We Instagrammed. We drank our hydrating drinks and ate our protein bars. And then…we were off!

Cycling through a deserted Manhattan

Up 6th Avenue we went, full of energy. It was pretty flat, the temperature was 10C (50F) and the riding was pretty easy. Along the way, stages featured live entertainment to keep us psyched.

Once we hit Central Park, the sun came out and music piped through speakers helped us tackle the hills. (I burst out laughing when the speakers started booming out “Sweet Caroline,” and hundreds of cyclists sang “Oh oh ohhhh” under their breaths as they pedalled.) Trees were in flower. Birds sang. Somewhere around 86th Street, in the middle of the park, we hit the “5 MILES” sign. I felt GREAT.

We popped out of the park and rode through Harlem, crossing 125th Street (Dr. Martin Luther King Boulevard). This was a part of the city I’d only seen from the train window on previous trips. I caught glimpses of various famous sites I’d only read about and was curious to stop, but I had to keep pedalling. Fodder for a future trip.

Soon, it was time to cross the Madison Avenue Bridge into the Bronx. This first bridge was relatively short and flat, compared to others we’d tackle later.

Our trip into the Bronx was quite brief. Soon, we were on the Third Avenue Bridge and cycling back into Manhattan, where we hit the 10-mile mark. I was still feeling pretty chipper as we cruised down Harlem River Drive and FDR Drive. Then we hit the Queensboro Bridge. This is a big bridge over the East River—so big, in fact, that it even has a song named after it (“The 59th Street Bridge Song,” for all you Simon and Garfunkel fans). And it was windy. But once we were across it, we were into our third borough, Queens, and soon saw mile marker 15.

Through Queens and Brooklyn

I’d be lying if I didn’t say I was getting tired at this point. Fortunately, there were two Five Boro Bike Tour rest areas in Queens where we could stop, get water and snacks, and enjoy some live music. I took advantage of them both, and soon saw mile marker 20. I was halfway.

Cycling this way really brings home just how enormous New York City is. In every direction, as far as the eye can see, there are apartment blocks and garages, shops and schools, bridges and highways, cars and trucks and bikes and strollers and dogs and squirrels, and so many people. Planes roar overhead. Subway trains rumble under your feet. Buses roar by. Music blares. Horns honk. We were on traffic-free streets the entire way, but there was an eerie sense of cacophony kept barely at bay. I loved it.

Then it was over the Pulaski Bridge, named for a Polish hero of the American Revolution, and into Brooklyn. Here, I’d hoped to see my sisters, my niece and my niece’s boyfriend (the latter live near the ride route in Brooklyn), but, as usual, I got my signals crossed. I tried to text when I was near, but we missed each other.

I did, however, note that the Williamsburg area of Brooklyn was a fascinating mash of blow-out salons (who knew you could make a whole business out of just drying hair?), organic pet-food stores, basketball courts, and clusters of traditional Jewish people with long beards and black hats watching the ride in seeming bemusement. I even spotted a man playing a cello in a deserted schoolyard.

At Commodore Barry Park, we hit Mile 26. I kept pedalling. After what seemed like hours, we hit Mile 30. I kept pedalling.

Brooklyn is really, really big.

Now we were on the southbound lanes of Interstate 278. It was a surreal experience to be with thousands of other cyclists (the event regularly attracts more than 30,000 riders) on a space normally reserved for cars. I would have enjoyed it more, if I wasn’t acutely aware of what was coming up: the Verrazano Narrows Bridge.

Across the longest bridge in the Americas

The Verrazano Narrows Bridge is 4.2 kilometres (2.6 miles) long. Think about that for a minute. That’s roughly the distance from Parliament Hill to Lansdowne Park. And it’s a bridge. A steep, windy bridge. And it was starting to rain.

That’s when I really started to question this whole Five Boro Bike Tour project.

Fortunately, the ride organizers had been out ahead of us and inscribed encouraging messages on the pavement that unfurled as we rode. Things like “You can do it!”

I mumbled them to myself as I pedalled, and pedalled, and pedalled. My legs were on fire. I saw people get off their bikes and walk, and I honestly couldn’t blame them. But I was determined to stay on the bike.

I geared down. I stood up. I pedalled. And then, I was at the highest point. Through my peripheral vision, I could see some pretty amazing views of New York Harbor. (And, to be honest, at that point I did get off the bike and admire the view for a minute or two.)

The grand finale of my Five Boro Bike Tour

From that point, it was all downhill—in a good way. I geared up, and up, and up, as we coasted gleefully down the slope and onto Staten Island. The Finish Festival was at Fort Wadsworth Park, and I proudly collected my medal, bought a t-shirt and got something to eat. But we weren’t done. It was only Mile 36. There were four more miles to go before the official end of the ride at Mile 40, the ferry terminal where we would catch packed-to-the-gills boats back to Manhattan. With one last burst of energy, I got back on the bike and pedalled the last stretch.

Later that day, an Epsom salts bath and a celebratory family dinner had never felt so good. (Or, as Neil Diamond would say, “So good. So good. So good.”) And, I must admit, I was proud of myself.

Want to try the Five Boro Bike Tour yourself? The basic registration is US$134 and the 2024 ride is on May 5. Just do it!

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As the owner of Ottawa Road Trips, I acknowledge that I live on, work in and travel through the unceded, unsurrendered territory of the Algonquin Anishinaabeg Nation. I am grateful to have the opportunity to be present on this land. Ottawa Road Trips supports Water First, a non-profit organization that helps address water challenges in Indigenous communities in Canada through education, training and meaningful collaboration.