The Mayor’s Cup New York City Kayak Championship is an elite kayaking race around Manhattan Island. This 26.7 mile marathon race is North America’s premier paddle sports event and soon to be New York City’s largest water event. The Mayor’s Cup drew some of the world’s and the regions most accomplished paddlers while raising money and awareness for the region’s most vigilant environmental group Riverkeeper.

Visit theMayor’s Cup websitefor more information and race results.

Herman Chalupsky from South Africa won the Mayor’s Cup with a time of 3:14:45. Followed by Greg Barton, Zsolt Szadovszki and Ian Gray. The Riverkeeper Cup was won by the Yonkers Paddling and Rowing Club.

Three hours into the second annual Mayor’s Cup Herman Chalupsky from South Africa rounded the southern tip of the island with Greg Barton, the two-time Olympic Gold medal winner in kayaking, on his slip. The two began surging 40 minutes from the finish. With $5,000 at stake, Herman leaned forward and hammered into the current and wind. Thousands of spectators leaned over the fence wildly cheering on Barton and Chalupsky as they neared the finish line.

See more of Jeff Chen’s Mayor’s Cup Photos

Riverkeeper, an organization dedicated to protecting the Hudson River, its tributaries and the watershed of New York City (, inaugurated NY Water Fest last year in collaboration with Ray Fusco, a former kayak guide whose dream was to create The Mayor's Cup Race around Manhattan.

Last year, 43 paddlers toed the line at the North Cove Yacht Cove on the Hudson in what was once the shadow of the World Trade Towers. Barton’s sole aim in 2006 was to break the record for rounding Manhattan in a kayak. (The record of 3 hours and 44 minutes was set by Dorian Wolters, a former member of the German Wild water Team.) He crossed the line in 3 hr 21 minutes and smashed the record by 24 minutes.

This year, Ray Fusco gathered more prize money, spread the word, and upped the total purse. Herman signed on and Barton suddenly had a worthy adversary. Zsolt Szadovszki, a former member of the Hungarian National Sprint Team, and South African Ian Gray, 11th at the US Ski Champs in San Francisco, also signed on. Now, this would be a race.

Nearly 100 paddlers toed the line. At the gun, a six-man pack sprinted up the Hudson: The Big Four were joined by Sean Brennan, a member of the US Olympic Sprint Team, and Dorian Wolter. Brennan and Wolter fell off early and the battle lines were drawn. Past Hell’s Gate at the tip of Roosevelt Island — roughly 6 miles from the finish, Ian Gray fell off and Zsolt dropped two boats back. Herman decided that the best way to slow Barton down was to pass him, so Herman sprinted ahead with Barton just behind.

One mile from the finish, Herman ran into a fishing line chest high. He tossed the line over his head and powered on, losing only a second or two. Barton was less fortunate; the line Herman tossed aside snapped back at him, catching first his paddle, then his torso, and finally his wrist watch. It took him 30 seconds to shake free. By the time both men were back up to speed, Herman was ahead by eight boat lengths, and Zsolt was back on Barton’s stern. Barton went after Herman, dropping Zsolt, but it was too little too late.

Herman finished in course record 3:14:45 – a dozen seconds ahead of Barton in a wild finish.

Riverkeeper’s mission is to protect the environmental, recreational and commercial integrity of the Hudson River and its tributaries, and to safeguard New York City’s and Westchester County’s drinking water supply.

Joe Glickman is a surfski and adventure racer who lives in Brooklyn. He finished the race in 3 hours, 28 min. 28 sec.