TD Five Boro Bike Tour Recap

I want to tell you I had an amazing weekend and this event was SO MUCH FUN. I really do.

For many people, I’m sure today was awesome. For me, today was very disappointing.


* * * * *

The TD Five Boro Bike Tour is a 40 mile car-free bicycling event put on by Bike New York. 32,000 bicyclists. $90 entry fee. Packet pick-up must be in person at the Expo. A great way to see The Big Apple! My friends and I managed to get signed up and planned a whole weekend around this.


Saturday we drove up to Staten Island to check in to our hotels. We then biked over to the ferry to Manhattan. If there is anyone that can make Philly drivers look like fine, upstanding ladies and gentlemen – it’s Staten Island drivers. Of course, we were on a more direct route … but when we crested the second hill, the sun setting behind us and casting a golden glow on the City before us … the view was spectacular and made the ride over worth it.

Biking to the Expo in Manhattan was a joy because of the absolutely lovely cycle track along the river with amazing views of Brooklyn.

Bikeway by the Brooklyn Bridge
Bikeway by the Brooklyn Bridge


On the way back it started to rain. Agreeing there’s no one to pick our butts up, we saddled up and rode back to the hotel. Did I mention we were in street clothes? Cotton is rotten in the rain. Acquired a hot shower and clean clothes before we got some dinner. We all agreed the tour would be super fun – lots of people and no speed records but a nice conversational ride with friends.


This morning we were assigned to the last wave of riders for the tour. We had initially rejoiced in this stroke of good fortune to be able to sleep in – until we missed the last ferry to make the official start time. No matter, there were lots of others still waiting for the ferry. We got to the start line about 20 min late, which we figured we could make up without issue. Until we hit the first wall of people. They aren’t kidding when they say 32,000 people sign up for this.


this was our view all day.
this was our view all day.



The parts of the ride that were awesome:

* rolling through the streets of Manhattan and Harlem. The Bronx and Queens were a bit rougher on the edges and Brooklyn lived up to its reputation as a hipster mecca.

* riding down the Brooklyn-Queens Expressway. Seriously – have you ever ridden your bike on a major highway?

* Bridges!

* Local musicians along the route keeping the vibe pleasant.

* fresh NY bagels at the rest stop we visited.

* Riding bikes! With Friends! in New York!


The parts of the ride I was incredibly disappointed about:

* Being Assigned the Third Wave. Dominated by cruiser bikes and folks who generally do not know how to ride in a group, much less a very large group. I don’t recall asking for the third wave or being told waves are assigned by expected average speed … or really anything. You’re just assigned a group.

* Walking. Entirely too much walking happened because of the rider volume, medicals (more people went down than I’ve ever seen in an organized event), and any sort of incline in the road. At one point we were stopped for somewhere around 30-45min just to get over a bridge. Due to volume.

* Being forced to take the mandatory shortcut because we failed to meet the cutoff time. Lopped 10 miles off our ride. See above for why. So sad because my friend was volunteering at the aid station on the cut miles.

* Other Rider Fatigue. My brain was fried from having to be hyper-vigilant in avoiding other riders that stop in the middle of the road, stop suddenly/without warning, walk their bikes across the road without checking to make sure no one is riding on the road, weaving, taking selfies while riding, etc.

(Some guy called me an asshole when I was passing and he drifted into me, touching my hip with his handlebar.)


* * * * *

I really feel like a heel for saying I’m disappointed in the event because I was riding with slower riders. There’s nothing wrong with being a weekend fitness cyclist or a cruiser cyclist or someone who only rides sometimes. Honest – I really feel this way.

But the truth is, had we been seeded with other cyclists at our similar abilities (but not the hammerheads) the day would have been completely different. Instead of trying to find clear passing lanes and walking entirely too much for a bike ride (i.e., at all), we would have had what we had looked forward to – a conversational speed bike ride.

It became a running joke to us that anytime we had to stop and walk was because there was a hill. Which is so sad but true – we walked so many hills towards the end because there was no room to ride. Everyone was walking because a few people weren’t able to cycle up the hill.

Eric, Phil and I during one of the "why are we stopped?" moments.
Eric, Phil and I during one of the “why are we stopped?” moments.


Based on my experience today, I can’t recommend this ride to anyone just yet. One of my friends did the ride last year and was in the first wave. She said the experience was so much better last year – she had no issues with walking or being stopped or having her ride cut short.  So I’d be willing to give it another try but only if I knew I would be in the first or second wave of riders.


See you on the road.

Author: Laura

wife. mother. kick-ass girl. all mountain, all road adventurer by bike.

6 thoughts on “TD Five Boro Bike Tour Recap”

  1. my sister and i were in the red group and it sounds like your wave had it much worse. while the views were amazing, the chances we did get to ride at a nice pace were nice given the location (central park and the qbe were my favorites), the waiting and the complete ignorance of some riders about basic riding etiquette was maddening. i think if it had been a warmer day – my patience would of worn out after the queensboro bridge rest area. glad i did it – but not sure i’d do it again….

    1. I had intense Other Rider Fatigue for most of the ride. Really draining to be hyper-vigilant all day! I posted to their Facebook page as well … third wavers shouldn’t suffer the sins of the organizers.

  2. It was my first time too and didn’t know what to expect. Was also assigned to the Silver group but lost my other 2 friends in the staging area so I hanged out at the vicinity of the tail end of the Red group, hoping to rejoin my friend when they let the Silver go. When the Red sea of folks went, there was about a 5 min gap before the Silver folks were told to start pedaling. When they did, I started pedaling in front of them and therefore was able to get into the front. That proved to be a good thing. After the national anthem and we’re told to start, I peeled off from the rest of the crowd, somehow managed to find and rejoined my friends, and we zipped through Manhattan and Central Park. We eventually caught up with the tail end of red and eventually the blue then it’s pretty much a good riding pace by then.

    Unfortunately, we had another friend that took her mountain bike and got stuck with the rest of the silver crowd. By the time she texted us, we’re several miles ahead of her and she was walking. So for next year, I’ll do the same thing in case I get stuck in the last wave again.

  3. I couldn’t even imagine what you had to go through… One of those “sounds great, till you actually have to do it” rides. Still, to ride in New York, sans cars, would be some kind of awesome.

    1. In talking with others it sounds like the experience is hit or miss depending on the wave. And given my proximity next year, I plan to try it again. The concept really is amazing. Plus you get to ride bikes on an expressway!

      1. The expressway part is what caught my fancy… THAT’S cool. Still, I don’t do well with the whole walking thing. My patience and tolerance levels on a bike suck. 😉

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