Five Boro Bike Tour Map

Five Boro Bike Tour Route

The tour starts and ends at Battery Park in Lower Manhattan. Participants line up behind the start line at Franklin Street and Church Street creating a queue which extends well south beyond the World Trade Center site.

The tour runs north up the Avenue of the Americas (6th avenue) past Macy’s and past the lions of the New York City Public Library before entering Central Park. After exiting the park the tour heads north through Harlem on Seventh Avenue and then crosses into the Bronx for a short 2 mile stretch before getting back to Manhattan and onto the FDR Drive. The FDR stretch of the tour runs south through Manhattan under Gracie Mansion before crossing the East River via the Queensboro Bridge into Queens. The first major rest area of the tour is in Astoria Park, Queens.

Leaving Astoria Park the tour proceeds south through Queens before crossing the Pulaski Bridge into Brooklyn, where it winds along the waterfront, past the Brooklyn Navy Yard. The route crosses under the Brooklyn Bridge, and then up and onto the Brooklyn Queens Expressway. The tour continues on the elevated BQE before dropping down to the Belt Parkway and over the Verrazano Narrows Bridge into Staten Island.

Once in Staten Island the tour makes a stop at Fort Wadsworth for a festival, before continuing the last three miles to the Staten Island Ferry where riders can take the ferry back to Battery Park in Manhattan.
From Wikipedia

Five Boro Bike Tour History

The event began on June 10, 1977 as the Five Boro Challenge with about 250 participants. The original tour was 50 miles long and started and ended in Queens.

What started as a one-time event became a tradition the next year when the New York City Mayor Ed Koch embraced the idea of a city-wide bike tour. The distance was shortened and the word “challenge” was changed to “tour” to make the event more appealing to the general public. That year, the number of participants increased tenfold to around 3000.
From Wikipedia