| 2005 |
| May |
| 2 | Executive Committee Meeting - 1900 |
| 13 | Spring Membership Meeting - Knights of Columbus 1800 |
| 28 | WYC Opening Day - Wicomico Yacht Club - 1200 |
| Jun |
| 1-5 | USPS Spring Governing Board - Charlotte, NC |
| 4 | Squadron Sail Day - TBA |
| 6 | Executive Committee Meeting - 1900 |
| 11 | Local Navigation Contest |
| Jul |
| 4 | Executive Committee Meeting - 1900 (possible reschedule) |
| 9 | Predicted Log Contest - TBA |
| 22-24 | D/5 Summer Council & Rendezvous - Solomons, MD |
| Aug |
| 1 | Executive Committee Meeting - 1900 |
| 13 | Squadron Crab Feast - TBA |
| Sep |
| 3-5 | D/5 Sail Regatta - TBA |
| 6-11 | USPS Fall Governing Board - Portland, OR |
| 10 | Squadron Sail Day - Mollies Point |
| 16 | Fall Membership Meeting - Knights of Columbus 1800 |
| 5 | Executive Committee Meeting - 1900 (possible reschedule) |
| Oct |
| 3 | Executive Committee Meeting - 1900 |
| 5 | Fall Boating Class Begins - Wicomico Library 1900 |
| TBA | Squadron Oyster Roast - Bart Quillin's Home |
| Nov |
| 7 | Executive Committee Meeting - 1900 |
| TBA | D/5 Fall Conference - TBA |
| Dec |
| 5 | Executive Committee Meeting - 1900 |
| 11 | Squadron Christmas Party - 1400 |
| 2006 |
| Jan |
| 2 | Executive Committee Meeting - 1900 |
| 5-9 | USPS Annual Meeting - Orlando, FL |
| Feb |
| 6 | Executive Committee Meeting - 1900 |
| TBA | Founders' Day Meeting - Knights of Columbus 1800 |
| Mar |
| TBA | Boat Show - Wicomico Civic Center |
| 6 | Executive Committee Meeting - 1900 |
| 7 | Spring Boating Class Begins - Wicomico Library 1900 |
| TBA | Change of Watch - Webster's 1801 |
| TBA | D/5 Spring Conference - Ocean City, MD |
| Apr |
| 3 | Executive Committee Meeting - 1900 |