The festive start, courtesy of Bike NY Over the bridges, courtesy of Bike NY A sea of cyclists< courtesy of Bike NY

NYC and the 5 Boro Bike Tour

United States Bike Tours

After having participated many times ourselves in this amazing tour, we wanted to bring the opportunity to you as well!

This 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 following year when New York City mayor, Ed Koch, embraced the idea of a citywide 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 cyclists.

Taking place the first Sunday in May each year, the adventure now begins in Lower Manhattan. The ride heads north through the heart of Manhattan into Central Park and continues on to historic Harlem and the Bronx, returning south along the East River on the FDR Drive. From there, it crosses into Queens and then Brooklyn, where cyclists take over the highway before making the thrilling climb up—and down—the Verrazano-Narrows Bridge to Staten Island. The route is 42 miles, mostly flat except for the bridges.

The ride finishes on Staten Island at a lively outdoor Festival, including bike demos, giveaways, games, a wonderful food concession, product samples, stretching, massage, a photo booth, and official merchandise on sale. Leave plenty of time to check out the exhibitors and activities and then visit the Fort Wadsworth Overlook for a scenic photo before continuing the final three miles to the ferry.

Having grown to its maximum capacity, the tour currently allows 32,000 cyclists the chance to own the streets of New York. It’s an incredible experience! The route is closed to traffic and a wave of cyclists as far as the eye can see surges along. Cyclists of every age, shape and size on bikes of every age, shape and size wheel their way through the amazing boroughs that comprise New York City.

Some text and photos courtesy of Bike New York.

This tour can be done in combination with our Tour of Three Cities or our Washington D.C. Tour!

Where You’ll Stay

3 * Travel Inn

What’s Included

  • 2 to 5 nights accommodations in the 3* Travel Inn
  • One day bike rental for the tour
  • Entrance fee to the tour

What’s Not Included

  • Meals
  • Bike rental for the remainder of the stay
TypeSelf Guided
Length3–6 days
From$458 Rates
Print Tour

Tour Dates

May 4, 2014

Skill Level

The Tour is 42 miles all on city streets without traffic. The route is mostly flat except for the bridges.

Day-To-Day Itinerary

  1. Arrival in New York City
  2. Participation in the 5 Boro Bike tour
  3. Explore NYC
  4. Explore NYC
  5. Explore NYC
  6. Departure

*Above and below is the suggested itinerary for a 6 day tour. Tour can be as short as three days or as long as desired.

DAY 1: Arrival in NYC

DAY 2: Participation in the 5 Boro Bike Tour: 42 mi/67 km

DAYS 3 through 5: Explore NYC
Included in the tour price is bike rental for the 5 Boro Tour with extended rental available for a supplemental fee. You will be provided with rental location, maps, and suggested routes.

One possibility is to cycle the Greenways of NYC.

A greenway is a linear open space, such as a path or trail, which links parks and communities around the city, providing public access to green spaces and the waterfront. Greenways expand recreational opportunities for walking, jogging, biking, and in-line skating.

In 1993, the City of New York had a vision to create 350 miles of landscaped bicycle and pedestrian paths that would crisscross the City's five boroughs and enrich the lives of all New Yorkers. Greenways answer the growing public demand for safe and pleasant ways to travel about the City. 

Book This Trip

Questions? Contact Us or Call 877-965-2064

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