| Frostbiting Awards | | |
| Single Handed Championship | | |
| 1st | | Joby Breck |
| 2nd | | Ryan Kinner |
| Season Championship | | Joby Breck |
| Long Course | | |
| Double Handed | | |
| 3rd | Wave Rider | Benoit Ansart |
| 2nd | Wily Silver Fox | Christopher Hall |
| 1st - 2nd Fleet | Skye | Ty Anderson |
| | |
| Division 2 | | |
| 1st | Hurricane | Alex Jackson, Jim Carey, John Schinto |
| Division 1 | | |
| 2nd | Carbonado | John & Daria Barry |
| 1st - The Commodore Sprague Trophy | Avalanche | Craig Albrecht |
| The Inverness Trophy | | |
| Overall Line Honors | Carbonado | John Barry |
| YRA Laser Awards | | |
| 3rd | | Oliver Repenning |
| YRA Ideal 18 Awards | | |
| 2nd | | Ellen Quinn |
| RYC Vespers | | |
| Division 3 | | |
| 3rd | Hearts Desire | Allen Lovejoy |
| 2nd | Team Vineyard Vines | John and Molly Baxter |
| 1st | Finn Ratoon | Bob Coulson |
| Division 2 | | |
| 3rd | Strange Brew | Randy Bourne, Eben Walker |
| 2nd | Finale | Tom O'Connell |
| 1st | Zuma | Stephen Chronert |
| Division 1 | | |
| 3rd | Team Zombie | Andrew Scrivan |
| 2nd | Skye | Ty Anderson |
| 1st | Hurricane | Alex Jackson, Jim Carey, John Schinto |
| Vespers Ideal 18 Awards | | |
| 3rd | | Sara Keller |
| 2nd | | Holly Pastula |
| 1st | | Chris Streit, Jeff Orum |
| Tin Horn Awards | | |
| Division 3 - 1st | Gramarye | Arthur Delmhorst |
| Division 2 - 1st | Strange Brew | Randy Bourne, Eben Walker |
| Division 1 - 1st | Wave Rider | Benoit Ansart |
| Captain Harbor Friday Night Series | | |
| Division 2 | | |
| 3rd | Team Vineyard Vines | John and Molly Baxter |
| 2nd | Nevermore | Ken and Drew Hall |
| Division 1 | | |
| 1st | Hurricane | John Schinto, Alex Jackson, Jim Carey |
| CHFNS Ideals, 3rd | | Nick Sheppard |
| Champion of Champions | | |
| 3rd | | Ellen Quinn |
| 2nd | | Ty Anderson |
| 1st | | Joby Breck |
| The Dot Trophy | | |
| 2nd Most Represented OD Fleet | | Ellen Quinn |
| Welsh Trophy | | |
| Most Representative OD Fleet | | Oliver Repenning |
| Nall Memorial Trophy | | |
| Greatest Participation & Season Score | | Ellen Quinn |
| Race Committee Award | | Chuck Zeigler |
| Anable Trophy | | Hurricane |
| Fleet Captains Trophy | | John & Molly Baxter |
| Puritan Trophy | | Will Logue |
| Press On Regardless | | John Schinto, Alex Jackson, James Carey |
| Turkey Bone Award | | Stephen Dolan, Richard Kosinski |