| Racing |  | Cruising | 
 
  |  | APRIL |  | 
 
  |  | Sat 14 | Early Bird, Ridout Creek (Meinhold) | 
 
  |  | MAY |  | 
 
  | Sailing World NOOD Regatta (AYC) | Fri 4 |  | 
 
  | Sailing World NOOD Regatta (AYC) | Sat 5 | Spring Rendezvous, Lake Ogleton (Maliszewski) | 
 
  | Sailing World NOOD Regatta (AYC) | Sun 6 | Follow the Wind cruise (Leigh) | 
 
  |  | Sat 19 | Maintenance Weekend, Mill Creek, Magothy R. (Lehman) | 
 
  |  | Tues 22 (til June 9)
 | South of Annapolis Cruise (Peek) | 
 
  | MRYC Annapolis to Miles River | Sat 26 | Memorial Day Cruise, Leeds Creek, Miles R. (Adams) | 
 
  |  | Sun 27 | Memorial Day Cruise, Dividing Creek, Wye R. (Adams) | 
 
  |  | JUNE |  | 
 
  |  | Sat 2 | Kids Cruise, Rhode R. (Pleisse) | 
 
  | Moonlight Race (PSA) | Sat 9 |  | 
 
  | Syronelle Regatta, Toronto | Sat 23 |  | 
 
  | Syronelle Regatta, Toronto Ted Osius Memorial Race (SCC)
 | Sun 24 |  | 
 
  |  | JULY |  | 
 
  |  | Sat 7 | start Block Island cruise (Cooper) | 
 
  | Boomerang Race (EYC) | Sat 14 |  | 
 
  |  | AUGUST |  | 
 
  |  | Sat 4 | Summer Rendezvous & Champagne Cruise, Beard Creek, South R. (Palmer) | 
 
  |  | SEPTEMBER |  | 
 
  |  | Sat 1 | Labor Day Cruise, Reed Creek, Chester R. (Lodge) | 
 
  |  | Sun 2 | Labor Day Cruise, Reed Creek, Chester R. (Lodge) | 
 
  | Race to Oxford (NASS) | Sat 8 | S'mores Cruise, Eagles Nest, Magothy R. (Foote) | 
 
  | Hammond Memorial Race (TAYC) | Sun 9 |  | 
 
  | Bruce Rankin Memorial Regatta | Fri 21 |  | 
 
  | Bruce Rankin Memorial Regatta | Sat 22 | Fall Rendezvous, PSA, Blackhole Creek, Magothy R. (Morris) | 
 
  | Bruce Rankin Memorial Regatta | Sun 23 |  | 
 
  |  | OCTOBER |  | 
 
  | Race to Rock Hall (PSA) | Sat 6 | Fall Cruise starts | 
 
  |  | Sat 20 | Football Cruise, Weems Creek (Gamber) | 
 
  |  | Sat 27 | Downrigging Weekend, Chestertown (Carter) | 
 
  |  | NOVEMBER |  | 
 
  |  | Sat 3 | Diehard Cruise, Broad Creek, Magothy R. (Leigh) | 
 
  |  | DECEMBER |  | 
 
  |  | Sat 1 | Picture Night (Helms) | 
 
  |  | JANUARY 2019 |  | 
 
  |  | Sat 12 | Annual Dinner |