Join the Five Boro Bike Tour

If the chapter inspired you to look beyond Manhattan, here’s where the real magic starts. New York may be made up of five boroughs, but only a handful of visitors truly take the time to experience them all.
One of the most exciting ways to do this? On a bike.

Whether you want a once-in-a-lifetime event like the Five Boro Bike Tour or just a relaxed ride through hidden neighborhoods, this guide helps you navigate NYC on two wheels — safely, smoothly, and with a healthy dose of adventure.

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1. The Five Boro Bike Tour: New York at Its Best

Every first Sunday of May, more than 32,000 riders take over the streets for the legendary TD Five Boro Bike Tour.
No cars. No honking. Just pure biking freedom through all five boroughs.

What makes it so special?

•   You bike 40 miles (65 km) through closed streets
•   You ride across iconic bridges, including the Verrazzano-Narrows
•   You pass through Manhattan, the Bronx, Queens, Brooklyn, and Staten Island
•   There are concerts, performances, and cheering crowds along the entire route
•   The atmosphere is electric — even if you’re not a seasoned cyclist

It is truly one of the few moments where the entire city feels united.

More info & registration: https://www.bike.nyc/events/td-five-boro-bike-tour/

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2. Bike New York: The Organization Behind the Movement

The Five Boro Bike Tour is organized by Bike New York, an incredible nonprofit that believes biking should be accessible to everyone.

In 2023, they taught over 30,000 New Yorkers how to ride a bike — many adults for the very first time.

They offer:
• Free bike education classes for kids and adults
• Safety workshops
• Community rides
• Beginner-friendly lessons in parks throughout the city

If you want to explore NYC by bike but don’t know where to start, this is the perfect place.

Explore their programs: https://www.bike.nyc/education/

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3. Want to Explore the Boroughs Yourself? Here Are the Best Routes

Even outside the big event, New York is amazing by bike.
A few unforgettable rides:

• Manhattan Waterfront Greenway (32 miles / 51 km)

A full loop around Manhattan — safe, scenic, and car-free along most parts.
Skyline views, riverside parks, and easy navigation.

• Brooklyn Bridge Park to Coney Island

Ride through the heart of Brooklyn, passing Red Hook, Sunset Park, and the ocean breezes of Coney Island.

• Randall’s Island to Astoria (Queens)

Perfect for a shorter, peaceful ride. Beautiful bridges, waterfront paths, and great food in Astoria.

• The Bronx River Greenway

A quiet alternative to busy Manhattan routes, full of nature and local charm.

• Staten Island’s North Shore Waterfront

Take the free Staten Island Ferry and explore a calmer, often overlooked borough with sweeping views of Lower Manhattan.

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4. Where to Rent a Bike in NYC

•   Citi Bike (NYC’s official bike-share system)

https://citibikenyc.com
Ideal for short rides, day trips, and quick hops between boroughs.
• Unlimited Biking
https://unlimitedbiking.com
Great for longer day rentals, guided tours, and better-quality bikes.
• Blazing Saddles
https://blazingsaddles.com
Perfect for exploring the Hudson River Greenway.

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Explore, Ride, and Let the City Surprise You

The five boroughs each have their own identity — their own food, architecture, rhythms, and stories.
And by bike, you feel that energy in a way you never could from a subway seat.

Whether you sign up for the TD Five Boro Bike Tour, join a community ride, or explore at your own pace, one thing is certain:

New York is at its best when you move through it — not just look at it.