| Trophy Name | Perpetual Descr. | Criteria | 2006 Winner | |||
| DERW | ||||||
| Combined Overall | ||||||
| Warburg | Monolith on Rock | 1st Overall | ARIANA Jeff Becton | |||
| Wilmerding | Sliver Tray | 2nd Overall | TERN Bob Johnstone | |||
| Becton Bowl | N/A | Fastest Boat, Cum. Elapsed Time | CYBELE Burnes/Rockefeller | |||
| Div. 1 | ||||||
| J-Boat Trophy | Half-model | 1st | FAR OUT Hal Kroeger | |||
| 2nd | SHEERNESS Scott Loweth | |||||
| 3rd | WEATHER GAUGE Stockton Smith | |||||
| Chreot | N/A | Best Score in 3 races | SHEERNESS Scott Loweth | |||
| Div. 2 | ||||||
| Morris | 1st | TERN Bob Johnstone | ||||
| N/A | 2nd | EVENTYR Gordon Haaland | ||||
| N/A | 3rd | BREAKAWAY Edmund C. Tarbell | ||||
| Div. 3 | ||||||
| Arthur F. Chace | N/A | 1st | ARIANA Jeff Becton | |||
| Ariana | N/A | 2nd | CRACKERJACK Alan Krulisch | |||
| N/A | 3rd | OTTER Henry Becton | ||||
| DERW Special | ||||||
| Downeast Trophy | n/a | Best Team Score | JAMBOREE Js (SIDEWINDER, BREAKAWAY, EVENTYR) | |||
| Janet Wilmerding | Tray | 1st Skipper Under 26 years old | SHEERNESS Scott Loweth | |||
| Nicholson | Stueben Whale | 1st Place, Crew Under 13 | BREAKAWAY | |||
| Chairman's Cup | Giant Mug | Person(s) doing most for regatta | Janneke Neilson | |||
| Sculpin Award | Most Spectacular Event of the Week | |||||
| NEVIN CUP | ||||||
| All Nevin Cup Trophise Awarded Based on Cumulative Corrected Time | ||||||
| Overall | ||||||
| Paul Nevin Cup | Overall Nevin Cup Winner | FAR OUT Hal Kroeger | ||||
| Div 1 | ||||||
| Div 1 - First | FAR OUT Hal Kroeger | |||||
| Div 1 - Second | WEATHER GAUGE Stockton Smith | |||||
| Div 2 | ||||||
| Div 2 - First | MISS MARVELOUS Pete DuPont | |||||
| Div 2 - Second | TERN Bob Johnstone | |||||
| Div 3 | ||||||
| Div 3 - First | ARIANA Jeff Becton | |||||
| Div 3 - Second | OTTER Henry Becton | |||||
| AUGUST CRUISE | ||||||
| First Day's Run | ||||||
| Div. 1 | Schooner Race Trophy | Fleet Annual Mtg | Div 1, 1st on 1st day of Cruise | WEATHER GAUGE Stockton Smith | ||
| Div. 2 | Coxe Trophy | Fleet Annual Mtg | Div 2, 1st on 1st Day of Cruise | EVENTYR Gordon Haaland | ||
| Div. 3 | Constance B. Madeira Trophy | Fleet Annual Mtg | Div 3, 1st on 1st day of Cruise | ARIANA Jeff Becton | ||
| Overall Trophies | ||||||
| Div. 1 | Pirate Cup | Fleet Annual Mtg | Div 1, 1st overall on points, no throwout | SHEERNESS Scott Loweth | ||
| Div 1, 2nd overall on points | FAR OUT Hal Kroegger | |||||
| Div 1, 3rd overall | WEATHER GAUGE Stockton Smith | |||||
| Div. 2 | Arundel Plate | Fleet Annual Mtg | Div 2, 1st overall on points, no throwout | TERN Bob Johnstone | ||
| Div 2, 2nd overall | EVENTYR Gordon Haaland | |||||
| Div 2, 3rd overall | BREAKAWAY Edmund C. Tarbell | |||||
| Div. 3 | Michael Crofoot | Fleet Annual Mtg | Div 3, 1st overall on points, no throwout | ARIANA Jeff Becton | ||
| Div. 3, 2nd overall on points | CRACKERJACK Alan Krulisch | |||||