Winners in 2006 came from the middle of the fleet, mostly small boats, well prepared and skillfully sailed. Crescendo, the Swan 44 MkII owned by Martin Jacobson of Greenwich CT, finished top boat in the series and took the Du Pont Trophy, second and third were Kalevala II a Grand Soleil 37 owned by Tapio Saavalainen of Washington DC, and Swift a Navy 44 skippered by Evan Scott of the US Naval Academy. The Indian Harbor Yacht Club team that won the Onion Patch Trophy included Crescendo, the J44 Brown-eyed Girl owned by Scott Dinhofer of Chappaqua NY, and the J130 Christopher Dragon owned by Andrew Weiss of Greenwich CT.
The Storm Trysail Red team, made up of Aera, Nick Lykiadopulo of the UK, Blue Yankee, Bob & Farley Towse of Stamford CT, and Googolplex, Colin Rath of New York were second, followed by Storm Trysail White- Orion, Pat Patterson of Virginia Beach, VA, Gold Digger, Jim Bishop of New York, and Dawn Treader, Larry Cohen of Gloucester, VA.
 2006 Overall Results | [ ] | 26 kB |
| 2006 Team Results | [ ] | 18 kB |