New York City's Massive Spring Bike Festival Crosses All Five Boroughs Car-Free

Though not as cyclist-oriented as Montréal — the most bike-friendly city in North America — New York is a great place to get around on two wheels. The city has the country's largest docked bikeshare program, and it's the starting point for the longest multi-use trail in the United States. The Big Apple also hosts large-scale cycling events like the TD Five Boro Bike Tour, a massive spring bike festival that invites riders on a car-free, 40-mile trip through all five boroughs.

Sponsored by the nonprofit organization Bike New York, the event has been running for nearly half a century. The NGO was born in February 1977 when 250 participants set out on a ride (then called the "Five Boro Challenge") organized by American Youth Hostels and the NYC Board of Education. The route traversed the city's five boroughs, with a single rest stop in the Bronx where riders could snack on complimentary hot dogs and sodas provided by Nathan's. However, it wasn't closed to traffic, so the cyclists' safety was at risk. Long story short, Bike New York, a group dedicated to promoting bicycle safety, was formed. Every year since, it has hosted the Five Boro Bike Tour on the first Sunday in May. 

These days, the event brings in more than 30,000 annual riders, including participants from over 60 countries. "Riding through the streets of NYC with no cars was such a great experience," said one cyclist from Philadelphia on TripAdvisor. "You'll cycle through the canyons of New York's financial district, past the stores and theaters of Midtown, through Central Park, Harlem, Queens, Brooklyn, and over the Verrazzano Bridge and into Staten Island," said another cyclist on Google, who described the ride as "awesome" and "one-of-a-kind."

The ride for 2026 is scheduled for Sunday, May 3. The route begins in Lower Manhattan and cuts north all the way across the island, cruising past the entire length of Central Park, the number one tourist attraction in America, along the way. Riders cross the Madison Avenue Bridge into the Bronx, looping around on the 3rd Avenue Bridge to re-enter Manhattan. The ride continues south, then heads across the Queensboro Bridge into Queens. 

After a north-south loop around Astoria Park, the route runs parallel to the East River, heading into Brooklyn. Catch a glimpse of the scenic Brooklyn Bridge Park before continuing south to Gowanus. Finally, pedal across the Verrazzano-Narrows Bridge to the finishing point and the lively end-of-ride festival on Staten Island. The last segment, according to past riders, is a highlight. "A real treat," said one cyclist from New Jersey. "The views of the harbor are tremendous and the breeze from the ocean cools you off nicely."

Online registration for the bike tour is required. Standard pricing for 2026 (for both adults and kids) is $179, and the registration includes complimentary bike repair and free snacks, drinks, and live entertainment at rest areas along the tour. There are a few more important things you'll want to know about: the tour takes place rain or shine, helmets are a must, and e-bikes are not permitted. To prevent excessive bicycle congestion on the car-free journey, riders are assigned to "waves" with staggered start time. Details are sent out to participants by late April.