Entrants
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| Yacht Name | Home Port | Captain | Date |
| SEA ROBIN (LITTLE HARBOR 37 - 37') | FIVE ISLANDS, ME | MACPHERSON, RUSSELL | 08/12/2021 |
| SPIRIT (IOD - 33') | MARBLEHEAD, MA | STAHLE, PETER | 08/12/2021 |
| VALIANT (12 METRE - 64.25') | MARBLEHEAD, MASSACHUSETTS | GREGORY, GARY | 08/10/2021 |
| MENAGE-A-TROIS (C&C 38 - 38') | MARBLEHEAD, MA | OGREN, PETER | 08/09/2021 |
| APOGEE (FRIENDSHIP SLOOP - 40') | BOSTON, MA | NORTON, ALEX | 08/08/2021 |
| ROZI (WOOD - 28') | MARBLEHEAD, MA | VAILLANCOURT, QUIN | 08/07/2021 |
| CHINOOK (HINCKLEY 41 STANDARD - 41') | MARBLEHEAD, MA | TORRIE, ALEC | 08/06/2021 |
| MASHNEE (BB30 - 46') | CAMBRIDGE, MA | TRAINA, ADAM | 08/05/2021 |
| ELEKTRA (IOD - 33') | MARBLEHEAD, MA | CORBET, CAROLYN | 08/04/2021 |
| WHEN AND IF (SCHOONER - 63.50') | NEWPORT, RHODE ISLAND | MAHER, JACK | 08/02/2021 |
| MISTOFFOLEES (ALERION - 33') | MARBLEHEAD, MA | ASPINALL, JENNIE | 07/29/2021 |
| VAGABOND (IOD - 33') | MARBLEHEAD, MA | MIGLIAZZO, MARC | 07/28/2021 |
| RELAPSE (IOD - 33.1') | MARBLEHEAD, MA | HARDY, CHRISTOPHER | 07/26/2021 |
| KUNGSORNEN (IOD - 33') | MARBLEHEAD, MA | CAMINO, ALEJANDRO | 07/19/2021 |
| BLUE PIGEON (SWAN 38 - 38') | MARBLEHEAD, MA | DOUB, JOHN | 07/19/2021 |
| BORDER ALLY (CUSTOM C&N - 43') | MARBLEHEAD, MA | GARRETT, LAWRENCE | 07/13/2021 |
| AIRTHA (ALERION EXPRESS 28 - 28') | NORTH HAMPTON, NH | SPIECKER, GEORGE | 07/12/2021 |
| VALKYRIE (SPIRIT OF TRADITION - 48') | GREENLAND, NH | KING, THOMAS | 07/10/2021 |
| MORNING WATCH (SEA SPRITE 34 - 33.84') | MARBLEHEAD, MA | RIPPBERGER, CHARLES | 07/09/2021 |
| MISIRLOU (CAL 40 - 394') | MARBLEHEAD, MA | EGAN, TOM | 07/09/2021 |
| ABIGAIL (KETCH - 39') | NOANK, CT | TERRY, JESSE | 07/04/2021 |
| JAVELIN (IOD - 33 FT') | MARBLEHEAD, MA | WIDNALL, BILL | 06/30/2021 |
| DORADE (S&S 52 MASTHEAD YAWL - 52.5') | NEWPORT, RHODE ISLAND | BROOKS, MATT | 06/30/2021 |
| POMPANO (IOD - 33') | MARBLEHEAD, MA | PETTER ETHOLM, TOM HUNTER | 06/28/2021 |
| GALAVANT (HERRESHOFF KETCH - 42') | ANNISQUAM, MA | TAGIURI, JOHN | 06/28/2021 |
| SOLUTION (CUSTOM - 50') | ROCKPORT, ME | BACON, CARTER | 06/24/2021 |
| BLACK WATCH (CUSTOM YAWL - 68') | NEWPORT, RI | FETTER, TREVOR | 06/23/2021 |
| NEITH (HERRESHOFF - 54') | MYSTIC, CT | BROWN, VAN | 06/21/2021 |
| AGLAIA (BUZZARDS BAY 15 - 25') | MARBLEHEAD, MA | FRIED, RICHARD | 06/20/2021 |
| MISTRAL TRIO (BRISTOL 34 - 34') | NAHANT, MA | MOTLEY, HERB | 06/19/2021 |
| BLACK MAGIC (HINCKLEY 41 - 41') | MARBLEHEAD, MA | WALTON, DAVID | 06/18/2021 |
| TANGO (IOD - 33') | MARBLEHEAD, MA | MORRISON, RACHEL | 05/20/2021 |
| NOVA (CUSTOM SLOOP - 3911') | GLOUCESTER, GLOUCESTER, MA | HARVEY, JONATHAN | 05/09/2021 |
| YANKEE GIRL (MORRIS 36 JUSTINE - 36') | MARBLEHEAD, MA | VANDER SALM, THOMAS | 04/23/2021 |
| VIKING (IOD - 33') | MARBLEHEAD, MA | MANCUSI-UNGARO, GREG | 04/05/2021 |
| GRACE (CONCORDIA - 41') | HINGHAM, MASSACHUSETTS | HERDE, MICHAEL | 04/02/2021 |
| GYPSY (IOD - 33') | SWAMPSCOTT, MA | DITTRICH, TIMMY | 04/02/2021 |
| PLEIONE (8 METRE - 48') | MARBLEHEAD, MASSACHUSETTS | DYSON, BRUCE | 04/02/2021 |
