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May 2025

46th Annual American Yacht Club Spring Regatta

May 3 - May 4
American Yacht Club, 499 Stuyvesant Avenue
Rye,NY10580United States
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This venerable event has racing for One-Design, ORC and PHRF Classes including Plus One, Non-Spinnaker, Doublehanded & Mixed Doublehanded.

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Oyster Bay Challenge

May 3 - May 4
Seawanhaka Corinthian Yacht Club, 314 Yacht Club Road, Centre Island
Oyster Bay,NY11771United States
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This invitational team racing event is sailed in Sonars.

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73rd Annual Samuel Wetherill Trophy Race

May 16 - May 18
Essex Yacht Club, 19 Novelty Lane
Essex,CT06426United States
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With a course of approximately 140 nm, Essex Yacht Club’s blue water race is open to ORC, PHRF and NEMA classes with doublehanded classes if possible. A Wetherill Club Trophy will be given to the yacht club with the best combined performance. Skippers introducing a new boat to The Wetherill receive a refund of 40% of the entry fee.

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Twenty Hundred Club Bridge Fiasco

The first of six unique and challenging races hosted by this adventurous club, this event starts at Halfway Rock just south of Prudence Island.

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The Alfred Roosevelt Regatta

May 17
Seawanhaka Corinthian Yacht Club, 314 Yacht Club Road, Centre Island
Oyster Bay,NY11771United States
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This event has a pursuit format, with boats’ handicap times applied at the start.

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5th Women’s 2v2 Team Race

May 17 - May 18
New York Yacht Club’s Harbour Court, 5 Halidon Avenue
Newport,RI02840United States
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This invitational event is hosted by New York Yacht Club Harbour Court in Newport, Rhode Island.

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Lloyd Harbor Yacht Club Spring Series – Race for the Case

May 17 - May 18

This 2-day series is sailed out of Huntington, New York.

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The 78th Block Island Race

© Rick Bannerot, Ontheflyphoto.net    First held in 1946, this Storm Trysail Club event is a qualifier for the North Ocean Racing Trophy (ORC), the Double Handed Ocean Racing Trophy (ORC), the New England Lighthouse Series (PHRF) and the Gulf Stream Series (ORC). It’s also a qualifier for the Caper, Sagola and Windigo trophies awarded by the YRA of Long Island Sound and the “Tuna Trophy” for the best combined ORC scores in the Edlu and Storm…

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World Sailing 2025 Team Race World Championship

May 28 - June 1
New York Yacht Club’s Harbour Court, 5 Halidon Avenue
Newport,RI02840United States
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This event is hosted by  New York Yacht Club Harbour Court in Newport, Rhode Island.

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Robie Pierce Regattas

May 29 - June 1
Larchmont Yacht Club, 1 Woodbine Avenue
Larchmont,NY10538United States
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Comprising the Robie Pierce Women’s Invitational (5/29) and the Robie Pierce One-Design Regatta (5/30- 6/1), this event for sailors with disabilities is co-organized by Larchmont and American Yacht Clubs and sailed in Ideal 18s.

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