Five Boro Bike Tour
The Five Boro Bike Tour is an annual recreational cycling event in New York City. It is produced by Bike New York. Conducted every year on the first Sunday of May, the 42-mile (68 km) ride includes over 30,000 riders. The route takes riders through all five of New York's boroughs and across five major bridges. The entire route, including bridges and expressways which normally prohibit cyclists, is closed to automobile traffic for the ride.
The tour starts at Battery Park in Lower Manhattan and ends with a festival in Fort Wadsworth, Staten Island, (the car free route continues from Fort Wadsworth to the Staten Island ferry allowing participants to make a complete 42 mile loop back to Manhattan). Participants line up at Franklin Street and Church Street, creating a queue which extends well south of the World Trade Center.
The tour runs north up the Avenue of the Americas, past Macy's, before entering Central Park. After exiting the park the tour heads north through Harlem on Seventh Avenue, crossing into the Bronx for a short 2-mile (3.2 km) section before re-entering Manhattan via FDR Drive. The FDR portion 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 at Astoria Park, Queens.
From Astoria Park the tour crosses south through Queens, over the Pulaski Bridge into Brooklyn, where it follows the waterfront, past the Brooklyn Navy Yard. After crossing under the Brooklyn Bridge, the route follows up and onto the elevated Brooklyn Queens Expressway. Before 2012 it dropped onto the Shore Parkway; in that year it continued on the below-grade Gowanus Expressway and climbed 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 (5 km) to St. George where most riders take the Staten Island Ferry back to Battery Park in Manhattan. Some New Jerseyans return home over the Bayonne Bridge instead.
The event began on Sunday June 12, 1977 as the Five Boro Challenge with about 250 participants, operated by Eric Prager and Sal Cirami. Eric Prager was commissioned by the New York City Board of Education to create a bicycle safety program. Sal Cirami worked for the school lunch program and was also an AYH Bicycle Committee leader. The two met by chance, and a brief conversation resulted in Sal inviting Eric to the next monthly Bike Committee meeting. Eric outlined his plans for his bicycle safety program at that February meeting. The original tour was 50 miles (80 km) 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 3,000.
From 1979 to 1990, Citibank was the primary sponsor of the event after one of its executives saw the ride. Due to financial problems, Citibank withdrew its support in 1991 and the tour was cancelled that year before returning in 1992. TD Bank eventually bought naming rights to the tour.
In 2013 the City proposed to charge the Tour nearly a million dollars for police services. 
- Schwartz, Sam (3 May 2012). "Five Boro Bike Tour will bring rolling street, bridge and highway closings beginning early Sunday morning". New York Daily News.
- City fee for bike tour By J. David GOODMAN, NY Times, 2013 April 4
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