Photos + Words : Charlie Sears / @thisischarliesears /


New York City, New York. – May 1st 2016


What a great way to kick off National Bike Month!

On the first Sunday in May, over 30,000 riders gathered in lower Manhattan for the largest charitable bike ride in the United States – The TD Bank Five Boro Bike Tour benefiting BikeNY. There was a 1000% chance of rain and sure enough, right about when the first wave of riders rolled off, the rain started too.

(So sorry in advance for water drops / blurry photos.)



I showed up at 5:30AM, well before the first wave of riders would leave the line. I prefer to show up well before an event starts so I can see the scene take shape. I thought 5:30 was early but NYPD had already been working since 2AM to block off our route.

As they say, “the early bird gets the worm” and luckily for me I was able to weasel my way into the VIP area and score some MUCH needed coffee and breakfast. Completely hit the spot and gave me the fuel I needed for the long day ahead.




What’s absolutely amazing about these photos of the start is that SURE – this looks like a TON of people, but this is just the first of FOUR waves of riders. Over 30 THOUSAND shredders were here so that means that there is “only” about 7,000 in these photos.









WAVE #2 :








I couldn’t hang around the start all day – I had to ride too – so I left with the tail of the second wave. The rain was coming down but that didn’t matter. The sights we’d see and the energy of the ride was all anyone needed to complete the next 40 miles.

In all honesty, I’m not familiar at all with the boroughs. This was my first time on this ride and my first time riding through most of these boroughs. I can’t really speak to much of the specifics of the route so here’s a (LINK) to the route map and I’ll just let the photos do the talking.



^ Inspiring. Take a closer look.





Suuuuch a sight for sore eyes to see that finish line as I descended the Verrazano Bridge. Also, suuuuuch a bummer it was raining! There was a band, all kinds of food trucks, games, and what looked like could have been a great time on Staten Island.

I grabbed a Chicken Parm AND a Meatball Parm samich (SO hungry – SO good!) from a vendor and quickly made my way to the Staten Island Ferry. It was still 3 more miles to the ferry and ‘cold’ doesn’t even begin to describe how I felt. My toes were numb and I was getting a sharp pain in my wrists from all the bumps / cold. I was soaking wet and so was my camera gear.

Crossing that line was SUCH a memorable moment though!




And that was the 2016 TD Bank Five Boro Bike Tour benefiting Bike NY!

If you ever get the chance to do this ride – DO IT! You will not regret it. I’m so proud of evvveryone who finished. I know I had a tough time (that Verrazano Bridge just kept goooooing!) and I’m so proud of all the men, women, and children that completed the ride! I’ll never forget this day and can’t wait til next year!


The TDFBBT benefits Bike New York – a 501(c)(3) nonprofit and New York City’s leading proponent of cycling as a practical, sustainable, and healthy means of transportation and recreation. Check them out!



Feel free to support The Awarewolfs while your at it. The gear we sell in our online store allows us the funds to go on these rides, host this site, and document events.



Photos + Words : Charlie Sears / @thisischarliesears /

One thought on “PHOTOS : TD FIVE BORO BIKE TOUR 2016

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