TD Five Boro Bike Tour

As someone who does not do much cycling at all, I couldn’t believe that I had signed up to bike 40 miles through all 5 boroughs of New York City.

Now that I’m done, I still can’t quite believe I did it! I biked (over) 40 miles through all 5 boroughs of New York City with basically no cycling training at all! And survived to tell the tale!

Starr on a bike in a neon yellow jacket, helmet, sunglasses, and facemask, with other cyclists in the background in NYC
Confession: Of the photos I got back from the official photographers, my posture is best in this one as I became increasingly deflated over the course of 40 miles and many hours 😅

It all started a few months ago, when we actually had booked different plans for the weekend of May 1. Part of what makes this achievement so hard to believe is that we cancelled a trip to an all-inclusive resort in the Caribbean that my friend found at a very low price (maybe a pricing glitch?) and we eschewed a long weekend of lounging and eating on a beach to ride a bicycle for 40 miles.

WHY, you may be asking, as we, too, asked ourselves several times in the days leading up to the bike tour, the uneasy feeling that we had made a potentially fatal mistake creeping in. (In jest, I may have told my brother that he could have my things if I did not survive the bike tour. I assumed my partner would also not have survived, in solidarity with me hahaha)

Well, because the TD Five Boro Bike Tour is:

One of the safest ways to experience biking in New York City, because the entire route is closed to car traffic. Nearly all of my cycling experiencing leading up to this tour was

  • Childhood biking around a quiet suburban neighborhood with extremely sparse car traffic
  • A few nerve-wracking bikeshare trips in DC where I would be so terrified of being hit by a car (like I saw happen to another cyclist my first day working full-time in District-proper) that by the time I docked my bicycle, I would be trembling from fear and from the fatigue of full-body clenching

So being able to ride for miles and miles with absolutely no fear of being hit by a car was really freeing! No cars! Just bikes! It’s safe enough for people to unicycle and penny farthing and tow their children behind them. The number one biggest threat to a cyclist on the road is, by far, automobiles, and without them, I felt incredibly safe and free on the roads.

The opportunity to bike on roads normally reserved only for cars, and thereby see the city from vantage points you’d never see unless you were zooming past in a car. For example, we were able to bike down a long stretch of the BQE (Brooklyn Queens Expressway), which is a straight-up highway. And, most excitingly, and the feature of the course that was the deciding factor for us to cancel our resort reservation and register for this tour instead, we were able to bike across the Verrazzano Bridge.

This was towards the end of the tour, so I’ll openly admit to walking my bike up the bridge because I was winded (Verrazzano-Narrows Bridge, Brooklyn to Staten Island)

A great way to kick off another attempt at “hot girl summer” with a physically active way to see parts of the city we’ve never been to. I’ve never been to Staten Island before, I got to experience crossing the Verrazzano Bridge and the view of Manhattan and the ferry as just a taste of this borough. We were warmly greeted at every borough and neighborhood by folks who would let us know: “Welcome to the Bronx!”, “This is Astoria!”, “You’re in Greenpoint!” I still remember making a goal in 2020 to do more NYC things since we spent so much of 2019 planning our wedding in the DC area, but of course the pandemic had other plans for us. We rarely get to leave our little area of our borough, let alone see all five New York City boroughs. Even though we only got just a taste of each of the boroughs of New York, we saw every single one, and I’m really encouraged to go back to many of the neighborhoods we saw and get a closer look at things I only saw in passing from a bike.

View of the RFK Bridge above countless cyclists at a resting point in Astoria Park (Astoria, Queens)

Why was I giving my bike tour buddies emergency contact information for in case I didn’t return? How was I preparing for this tour??

Well… I will admit I didn’t prepare much! About a month before the tour, I started heading to the gym to use the stationary bikes just to get myself used to pedaling for several hours. Immediately, I learned that I am going to need some padded bike shorts because the bike saddle began hurting my crotch after just 15 minutes. I think I actually started avoiding the gym after this, both because it became very crowded as COVID cases in NYC began rising rapidly again and because well… I had a bad time.

About 3 weeks out, we took New York City’s bikeshare bikes – Citi Bike – to do the Central Park bike loop. I learned that my partner had actually not ridden any bicycle since he was a teenager (!!) and he definitely felt discouraged by how laborious the Central Park ride was: it’s a very hilly park and bikeshare bikes are designed to be rather heavy so as to be sturdier, especially for novice riders. After a very tiring loop around Central Park, which was still honestly very exhilarating! and fun! on a ridiculously beautiful day!, we assured him that the bikes we were renting for the tour would be much lighter and easier to ride.

We did another little bike day about 2 weeks later, when Car Free Day NYC was happening the weekend after Earth Day, and took advantage of the free Citi Bike day pass to ride up the Hudson River Greenway, which has an incredibly lovely bike path. It’s a separated, dedicated path for just cyclists (and scooters and skaters, on some parts of it) and it wasn’t very crowded at all on, again, a luxuriously beautiful day.

And that’s about it! The day before the bike tour, we picked up our rental bikes and biked home, having made the mistake of not wearing our padded bike shorts for this ride home that left me in pain as soon as our bike tour started. The night before, we packed a backpack for the ride, learned that bags strapped over the shoulders were prohibited, re-packed things into our handlebar bags and fanny packs, and tried to sleep through the anxiety of what was a really daunting task we knew we did not prepare enough for.

By the time we reached the Queensboro Bridge, it was QUITE thick with cyclist traffic, so we took in the sights while walking across.

The morning of the race, as we headed to the starting line, we saw cyclists from the earlier waves whizzing down the empty streets. It was another perfect weather day for biking and we really relished it. Even though we lost steam halfway through and the second half took us twice as long as the first half, we had a lot of fun biking through New York City, seeing the sights from the typically car-dominated streets, and basking in the gorgeous weather. It took us a veeeeeery long time to get from the finish line to home, because the crowd was so thick and it took us about an hour to return our rental bikes and almost 2 hours to get onto a ferry, during which time the weather soured from sunny and warm to cold and windy.

But we have zero regrets and are even considering doing it again next year! Who knows, maybe we’ll even get bikeshare memberships or even purchase bicycles to ride on weekends or to actually get from place to place.

2 thoughts on “TD Five Boro Bike Tour

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