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The Most Beautiful Ensign Trophy, to recognize pride and enthusiasm in the upkeep of one's Ensign, shall be awarded at the National Championship Regatta. Any Ensign owner may compete for this trophy, the winner of which will be selected by a panel of judges. The criteria for this award will be based, on but not limited to, rigging, ingenuity, surface finishes, and overall presentation. No boat may win this award two years in succession.
Past winners of the Most Beautiful Ensign are listed below:
| YEAR |
BOAT |
SAIL |
OWNER |
FLEET |
| 2024 |
SMOKE |
1253 |
Ward Woodruff |
73 |
| 2023 |
MOXIE |
425 |
Colin Irish |
35 |
| 2022 |
DEBBIE DOES BROOKLYN |
1483 |
Benjamin Stern |
21 |
| 2021 |
IRISH EYES |
1643 |
Neil Lynch |
35 |
| 2020 |
|
|
Not awarded |
|
| 2019 |
ELMO |
612 |
Stephen & Wendi Heinzelman |
23 |
| 2018 |
DOLCE P |
1511 |
Mike Paccione |
63 |
| 2017 |
MADLEY |
794 |
Bryan Flynn/Bernard Bentgen |
12 & 31 |
| 2016 |
SEA FOAM |
1154 |
Niantic Bay Sailing Assoc. |
73 |
| 2015 |
ZONKER |
752 |
Colin and Carrie Irish |
35 |
| 2014 |
HALLELUJAH |
257 |
Bob Jackson |
51 |
| 2013 |
IRISH MIST |
710 |
Dick Torpey |
63 |
| 2012 |
MENEKAUNE |
1392 |
Mike Derusha |
12 & 35 |
| 2011 |
SWOOSE |
11 |
Russ Carr |
57 |
| 2010 |
CHETHER |
1412 |
Andy Bohn |
31 |
| 2009 |
SCARLETT |
880 |
Erik Rosanes |
7 |
| 2008 |
ENDURANCE |
1033 |
Pete Kogut |
23 |
| 2007 |
MAGIC |
363 |
Robin Durrschmidt |
34 |
| 2006 |
ALTITUDE ADJUSTMENT |
1410 |
Jon & Jenny Ogborn |
43 |
| 2005 |
NIGHTWIND |
458 |
Ward Woodruff |
34 |
| 2004 |
ALTITUDE ADJUSTMENT |
1410 |
Jon & Jenny Ogborn |
43 |
| 2003 |
TAILGUNNER |
496 |
Gary & Louise Woodruff |
73 |
| 2002 |
ENSANE |
1742 |
Brian Simkins |
7 |
| 2001 |
VENGEANCE |
1667 |
William Gentzlinger |
7 |
| 2000 |
GIGI |
1286 |
Todd Snyder |
31 |
| 1999 |
CRISIS EXPRESS |
957 |
Barry S. Friedman |
10 |
| 1998 |
TALISMAN |
524 |
Charles Bessant |
10 |
| 1997 |
POS |
1127 |
Dave Brooks |
69 |
| 1996 |
BREEZIE WEEZIE |
1487 |
Dave Parlin |
31 |
| 1995 |
TEKUMSEH |
276 |
Joe Arbaugh |
31 |
| 1994 |
VENGEANCE |
1667 |
William Gentzlinger |
7 |
| 1993 |
QUEST |
739 |
Dave Warters |
2 |
| 1992 |
ENDURANCE |
1033 |
Peter Kogut |
23 |
| 1991 |
SPUN SUGAR |
5 |
Mike Little |
2 |
| 1990 |
WATERCOLORS |
170 |
John O’Connell |
30 |
| 1989 |
IRISH MIST |
710 |
Dick Torpey |
63 |
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