By Steve Bauman

It was February 1977–too cold for cycling, but not for warm thoughts about riding through the streets and parks of New York City. Little did we know that our love of cycling was going to lead to the largest mass cycling event in the United States. And it all started with a question posed by a New York City schoolteacher.

Year One: The Five Boro Challenge

American Youth Hostels encouraged people to cycle for years–in the early days of hosteling, young people were expected to cycle or hike from hostel to hostel! Eric Prager was commissioned by the NYC Board of Education to create a bicycle safety program. One of Eric’s co-workers was Sal Cirami. Sal 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.

It was thus that the “Five Boro Challenge” was born. We’d have bike clinics for students on safety and repair and have a day trip around the five boroughs to practice the safety rules. Unlike recreational rides at the time, which took place in the countryside, the Five Boro would celebrate the urban landscape. Easy and simple. The date would be Sunday, June 10, 1977. We threw ourselves into the project. This could be fun!

Five high schools would participate with 50 or 60 students along with about 200 members of bicycle clubs. (Why should just the students have a good time?) Our route would be 50 miles starting and ending in Flushing, Queens. We’d ride to Brooklyn and go over the Verrazano-Narrows Bridge into Staten Island. The Staten Island Ferry would bring us into Manhattan and then we’d ride up to the Bronx and back to Queens over the Throggs Neck Bridge. The plan was set.

The night before the “Challenge,” eight or nine leaders slept on the floor at my house. At 6:00 a.m. they registered the entire group at the Unisphere in Queens–no entry fee, and there was even a sponsor: Nathan’s gave out hot dogs and soda at the one and only rest stop in the Bronx.

Our route was not closed to traffic as it is today. But we had two police cars, one in front and one in back, each with two police officers. Some 45 minutes into our ride, it became clear that we hadn’t planned on how we were going to get all 250 of us through the intersections at once. We were being separated by red lights and slower cyclists. Our police escort decided that some traffic regulations had to be broken and they allowed our leaders to block traffic at cross streets so we could all pass–even after the light turned red. Thus, the Tour marshal was created.

We had a wonderful time, but we didn’t imagine we’d be riding the next year, much less the next 30.

Beyond a One-Time Event

When Ed Koch became mayor in 1978, his administration sought ways to promote bicycling. Charlie McCorkle of Transportation Alternatives along with the AYH group and leaders of other New York cycling organizations took the “Five Boro Challenge” idea to City Hall. The mayor’s office loved it, but the word “Challenge” made the Tour sound too difficult for a family and friends to ride, and the miles had to be reduced to an easier 35 or 40. After three hours of brainstorming the “Five Boro Bike Tour” name was born. It had a nice ring to it and clearly conveyed that all of New York City was open for cyclists.

The second year we were no longer a day trip but an Event! We had support services from Emergency Medical Services and the New York City Fire Department. The Department of Transportation coordinated the involvement of City agencies and cooperated with the NYPD to make the route traffic-free. They used the leap-frog system with waiting points about 40 blocks apart so they wouldn’t have to close the entire route down to traffic all at once. The police blocked traffic for the first 40 blocks, then held us there while they leap-frogged ahead to close the next section to traffic.

The City limited the Tour to 2,500 cyclists, but we ended up with 3,000. We cycled on highways for the first time. The Tour started at City Hall, traveled to Brooklyn, Queens, Randall’s Island, and the Bronx, then back to Manhattan where we all boarded the ferry to Staten Island. We rode down Bay Street on Staten Island, made a U turn, and took the ferry back to end the Tour in Battery Park.

At the end of the ride the assistant police chief inspector said, “If we do this enough we’ll get it right.” We took this as a good sign.

We also got a benefactor. The U turn on Staten Island had created quite a traffic jam, and we trapped a curious spectator who was enthralled by what he saw. He happened to be the vice president of community service for Citibank, and he resolved, right then and there, that he wanted this Tour for his bank. On Monday he talked with his colleagues about what he’d seen, and Citibank became the sole sponsor for the next 11 years.

In 1979, the Tour started in Battery Park. It’s been the launch point ever since. Over the next few years, we also experimented with some route changes, especially in Brooklyn where we just got too big to continue to go through residential neighborhoods. And we grew by leaps and bounds. In 1979, we jumped to 7,500 participants.

A Big-Time Event


A major New York City happening in 1980 drove up the number of riders to 12,000. A month before the Tour there was a subway strike. AYH set up a phone bank to answer questions about cycling as transportation to and from work. Transportation Alternatives put up bike route signs on New York City streets, and the whole effort was done in cooperation with the City. Mayor Koch held a press conference and pointed out how Beijing residents used bicycles as the preferred way to get around and that New Yorkers should travel by bikes during the strike. And they did. Bicycle sales soared and New Yorkers were caught up in a cycling craze. The Five Boro Bike Tour was the thing to do.

No question about it, the Tour was big. By 1981, just as today, the roads were closed to traffic about an hour before the Tour arrived and opened shortly after the Tour passed. To minimize traffic congestion and the demand on police, and to show riders a variety of different views of New York, we still utilize a mix of highways and streets for the Tour route.

A head of state participated with 17,000 cyclists in 1982. The Dutch fleet was in town to celebrate the 200th anniversary of diplomatic relations between the Netherlands and the United States. Being from a country of cyclists, they had their bikes on the ships. Two hundred sailors led the ride wearing special naval cycling uniforms. As it happened, the prime minister of the Netherlands was a professional bicycle racer in his youth, and he decided to ride from Fort Wadsworth, Staten Island, to the ferry.

The Festival became a logistic necessity when the number of riders no longer fit on a single ferry. Snug Harbor and Von Briesen Park were early hosts, before the use of Fort Wadsworth was secured in the early 1980s. Soon exhibitors and entertainment became part of the event.

Recession hit the Tour in 1991, when Citibank had to withdraw its support, causing a one-year hiatus for the event. After the ride was re-established in 1992, finding sponsors became part of the work of operating the Tour.

The Bike Tour continued to grow, becoming more and more of a full-time operation for a few people. Each year brought a new challenge–right up to and during the ride. In 1983 we experienced rain. Real wet, cold, constant rain from start to finish. In the late 1980s a small portion of the Brooklyn-Queens Expressway collapsed just 10 minutes before the Tour was to arrive. One year in the early 1990s, a steam main broke just as we were to start the Tour, and Sixth Avenue became a sea of molten asphalt.



Proceeds from the Tour helped build the first official Hostelling International hostel in New York City, on the Upper West Side. Five Boro organizers also had a direct hand in helping to establish large-scale urban rides in other cities, including Boston, San Francisco, and Montreal.

By 1999, AYH decided that the Tour needed more attention and spun off the event into a new non-profit organization named Bike New York (est. 2000), which has grown to include smaller rides and, in a tradition stemming from the very first Tour, a flourishing Bicycle Education Program. In 2007, Bike New York proudly welcomed a new title sponsor for the Tour.

More than 30 years after its founding, the Tour has become a much-beloved springtime tradition for its 30,000 participants–yet it still retains the simplicity and friendliness of the first ride.

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