Why My First 5 Boro Bike Tour Was A Bust

In my short time as a bike owner, I've come to realize that New York City is not the most bike-friendly city - especially for someone just starting out. Sure we have miles and miles of designated bike lanes - but these lanes are part of busy streets where cyclists are forced to dodge buses, pedestrians, taxis and more. 

In 2013 there were 6,328 reported bicycle/motorist crashes in NY. So when I read that NYC is ranked #1 in "Bike Friendly Cities" I am verrrry skeptical of the criteria. 

But once a year, in the spring, 40 miles of NYC roadways become a playground for cyclists. In it's 40th year, the TD Bank 5 Boro Bike Tour is a chance for biking fans of all ages to ride all day with no fear of cars, buses, tourists or taxis. 

It's just you, your bike and open road. Oh, and over 30,000 other participants. 

For years I've heard how wonderful the TD Bank 5 Boro Bike Tour is. I know many people who insist you have to do it at least once, while others sign up year after year. 

Once I had a legit road bike, I knew I wanted in. I paid the steep entry fee (around $100) a few months ago and before I knew it, it was time to start preparing for the ride. 

TD Bank 5 Boro Bike Tour 2016


I didn't do a lot to "train" for this bike ride. The 40 mile distance was intimidating, but in the end, I knew that it was a no pressure, casual ride and I could likely make it to the finish. Especially after my journey over the GW Bridge and into the Palisades, a ride that ending up totaling around 38 miles, I knew I had it in me. 

I attempted to do one more long ride the weekend before the tour, but I ended up falling off my bike and quitting. 


I had been told to expect some crowded areas during the ride, as cyclists of all skill-levels are out there. There are people with carbon fiber tri bikes and there are also people out for a joy ride on their Citi Bikes. 

I was expecting a lot of stop and go and to be surrounded by some people even more  uncomfortable on their bikes than I am - so I had my platform pedals put back on my bike before the ride. 

No thank you to clipping in and out and being petrified for 40 miles. 

Biking is NOT a cheap hobby, I'm coming to learn, nor is it convenient. I now need to get my bike back to a shop to have my clip-less pedals reinstalled. Will the headaches of cycling never end? Sorry, I'm being a grouch. 


TD 5 Boro Bike Tour

In order to pick up my ride packet, I made my way over to South Street during my lunch break, where the expo was being held.

It was almost exactly like any running expo I've been to which meant sampling a lot of granola bars and taking any free thing that I could only to get home and say, "I HAVE NO USE FOR THIS WHY DID I TAKE A FREE PENCIL!?" 

As per usual, I spent unnecessary money on something because, "It's SUCH a good deal!" And workout clothes are my weakness. I walked away with my first cycling jersey - the Giro Ride short sleeve jersey in WILD LIME. It's retail price is $100 and I snagged it for $30 so I don't feel too guilty. 

As part of each participant's packet you get a bib to pin to yourself, a bib to twist-tie to the front of your bike, and a helmet cover that says TD 5 Boro Bike tour! No ride shirt BOO HISS. 


Once I was done frolicking in the sunshine at Bear Mountain on Saturday it was time to face the facts - the forecast for Sunday's bike ride was miserable. Starting at 8 a.m. there was a 50% chance of rain throughout the morning. And it was a cold, windy rain too. 

My professor from grad school, who I was supposed to meet up with at the start, decided that it wasn't worth it. But I'm poor, and the fact that I had spent $100 for this bike ride made me feel obligated to at least give it a try. 


In order to get more rain-free miles in, since I didn't expect to slough it out for all 40 miles, I rode to the start from my apartment. It was about 7 miles total, and the fact that I wasn't clipped in made it a whole lot less stressful. It also helped that it was 6:45 a.m. and the roads were basically car-free. Plus, as I got close to the start, there were tons of other 5 Boro Bike tour participants headed to the corals that I could follow. Directions aren't my specialty, so I was happy to have people to guide me. 

I found my way to the coral and waited for Wave 2 to be sent on our way at 8:10 a.m. 

As I sat in the corral waiting to start, I looked around and realized that thankfully, I was by no means the only cyclist without fenders on my tires. I knew going fender-less would result in lots of wet, muddy spray from the ground, but the price tag just wasn't worth it to me. $50+ to buy them and have them installed is a lot when I don't plan on making rain-rides a regular occurrence.

There were a lot of people at the start who seemed to have plastic bags or shower caps around their feet which would have been a good call - I'm clearly not a seasoned pro when it comes to dressing myself for 40 mile bike rides. 

Looking back, I probably would have lasted longer had I dressed warmer, but, c'est la vie!  I wore: 

  • Icebreaker Merino Wool Beanie under my helmet
  • Long Sleeve Dri-Fit Shirt 
  • Fancy Shmancy Nike Winter/Rain Jacket 
  • Northface Fleece Lined Winter Running Leggings 
  • High socks over my leggings 
  • Buff
  • Winter Bike Gloves 
  • SPIbelt

After some speeches from TD Bank execs (I have a strange obsession/love for TD Bank) and race directors, we were off! 


I noticed lots of people with interesting things attached to their helmets in an effort to keep their sights on people in their groups. There were pineapples and beers that made me laugh.

The ride started up 6th Avenue and it was awesome riding through midtown with not a car in site! Hellooooo Bryant Park! Hey office! Lots of TD Banks that we passed had employees out cheering the riders on. 

Though the rain started promptly at 8:00 a.m., I was surprised at how high everyone's spirits seemed. There was lots of "Woo"ing and laughing and jokes around me. And for awhile, I was really diggin' the ride more than I had expected. 

While there were certainly tons of other people out there, it wasn't ever horribly congested - especially since I wasn't looking to break any records with my speed!

We made our way up to Central Park and I considered ducking out at Engineer's Gate to go to my apartment but decided to keep going. 

There were a few parts where you had to stop at crosswalks to let pedestrians through, but nothing too obnoxious. Everyone seemed to be having a great time which confused me a little because the weather was so miserable but, maybe those people were dressed warmer than me! 

Up in the 100s I started getting more and more cranky and after a quick stop to use a portapotty I decided that when I approached 96th Street on the FDR I would peel off the route and head home.

But before that, there was a quick roll through the Bronx (I can't believe how short the course in the Bronx is!) and over two bridges which was again pretty darn cool. 


I headed home after about 12 miles on the course for a total of 20ish for the day. Though it was cold, lonely and wet (not to mention uncomfortable considering all the bruises I got at Bear Mountain) I was proud of myself for doing it at all. I was just bummed that the weather had ruined what would have been an awesome, fun day in the sunshine! 

I guess there's next year? (Except not really, because I've sworn off paying lots of money for bike rides that could end up with a forecast like THIS - not worth it to me!) 

When I got home, I scrolled through Instagram and realized just how many 10K, half marathon and marathoners had trudged through the rain that morning as well. Special shout out to my best friend Allison for running her second half marathon in those conditions!