The Five Boro Bike Tour Is The Best Way to Experience New York City

I can’t believe it took me so long to do the Five Boro Bike Tour! I’ve experienced this city from 1,000 different perspectives over the years from a very young age, long before I lived here. But I’ve never experienced NYC in such a complete, wholesome way in a single outing as riding the Five Boro Bike Tour.

For anyone thinking about doing the Five Boro Bike Tour for the first time, or if you’ve done the ride multiple times, or if you never even knew it existed, this series of posts has something for you. Meant as a resource for newbies and veteran riders alike.

About the Five Boro Bike Tour

Probably the clearest way to understand the scope and scale of the Five Boro Bike Tour is to view the tour map. Below is a cool map from Ride With GPS that shows the route, plus elevation along the route. Explore it; it’s interactive and fun.

A brief History of the Tour

The Five Boro Bike Tour, now known as the TD Five Boro Bike Tour, began in 1977 as the Five Boro Challenge, initiated by the American Youth Hostels (AYH) and the New York City Board of Education. It started as a bicycle safety training program for high school students, culminating in a 50-mile ride through all five New York City boroughs— Manhattan, Brooklyn, Queens, the Bronx, and Staten Island. The inaugural event on June 12, 1977, had about 250 participants, including 50 students and 200 bike club members, starting and ending in Flushing Meadows-Corona Park in Queens. The route included the Verrazano-Narrows Bridge and a ferry ride from Staten Island back to Manhattan.

In 1978, Mayor Ed Koch endorsed the event, turning it into a citywide tradition. The route was shortened to 40 miles, and participation grew rapidly, reaching 3,000 riders by 1978 despite a city-imposed cap of 2,500. The tour’s popularity led to logistical innovations like the “leapfrog” system, where police closed sections of the route in stages to manage traffic. From 1979 to 1990, Citibank sponsored the event, but it skipped 1991 after Citibank withdrew and no replacement sponsor was found. TD Bank became the title sponsor in 1992, and the event has run annually since, except in 2020 due to the COVID-19 pandemic.

By the late 1980s, attendance ballooned to 32,000, a cap Bike New York, the nonprofit that has organized the tour since spinning off from AYH in 1999, maintains to this day. The tour became a charitable ride, funding Bike New York’s free bike education programs, which have taught bike skills to over 100,000 New Yorkers since 2007. The 40-mile, car-free route, crossing five major bridges (including the Queensboro and Verrazano-Narrows), showcases NYC’s diversity and architecture, attracting cyclists from every state and dozens of countries. Now in its 48th year, it’s the largest charitable bike ride in the U.S., blending community, advocacy, and urban exploration.

To Learn More about the Tour

By far the best way to learn about the Five Boro Bike Tour is to check out the Bike New York website.

From there you can:

Register — To register you’ll be redirected to Let’s Do This which is The Official Registration Partner for the event. (Here you can also explore a whole list of other events—including running, road cycling, triathlon, duathlon, swimming—all across the United States and the world. Cool Site. Check it out.)
View the Start Schedule — When you register, you choose your skill level and whether you’ll be riding with a group (you can select a team name and have fun with it). A few days before the ride, you’ll be assigned a Wave (1 thru 5 color-coded), which will include a start time and meeting location, shown in the Start Map.
Packet Pickup — Where you’ll get instructions on how to pick up your Rider ID Kit. Which includes bib numbers to attach to your shirt and bike, a branded helmet cover, and additional rider info. This process was so smooth and easy. It was the first glimpse I had about how well-organized the event was.
Read their FAQ page — Important info about rules, general info, etc. For example, you’ll want to know about what kind of bikes you can use, whether you’ll need to wear a helmet (yes), which bags are prohibited and allowed (important), and so on.
Bike Rental — Unlimited Biking is the official rental partner of the Bike New York. For my ride, I rented an aluminum road bike from them—I share more about my experience below.
Lodging — Where Bike New York links you with their lodging partner.
Maps — Various maps, including Route Map and Start Map.

Things You’ll Need (and want) For The Five Boro Bike Tour

The section covers your material needs, such as apparel, gear, nourishment and bikes. In another section we’ll review best practices to prep for the ride.

Bike

You guessed it. You need a bike to ride the Five Boro Bike Tour. But you don’t necessarily need a TREK Madone SLR!

According to the FAQ section on Ride NY website, here are the kinds of bikes allowed by the Tour. ↓

Any human-powered pedaled bike (recumbent, unicycle, tandem, tricycle, etc.) is permitted, with the exception of surrey or party bikes (equipped with steering wheels).
Class 1 pedal-assist e-bikes may be used on the Tour.
Note: Class 2 or throttle e-bikes are not permitted on any Bike New York events, even if the throttle function is disabled.

Your Own Bike, Or Bike Rental?

There are some pros and cons to riding with your own bike or renting a bike. But if you have a decent road bike, it makes sense to use your own bike. Pro Tip: Consider having your bike tuned up a week before the ride.

I rented a bike for the Tour because I have a very old mountain bike, which happens to be too small for me. (More about that later.) Renting gave me the chance to try a proper road bike, sized correctly for my 6’3″ frame. I ended up going with Unlimited Biking for my rental. (In an upcoming post, I’ll share more about my personal experience with Unlimited Biking.) I choose to rent a Cannondale road bike, aluminum frame. They also had a carbon fiber frame options—which were too expensive, honestly.

Lastly, one nice thing about renting was the drop-off. The drop-off point was near the Staten Island Ferry, so the ferry ride and subway back home was bike-free and relaxing.

So, assess your personal bike ownership situation to decide if renting make sense, but at least you know it’s an option.