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Re: St Mary's Gov Cup / other Chesapeake Bay races
Down the Bay is less popular because it's a very long, upwind slog. A lot of people simply can't set aside the amount of time from work and family to make the deliveries and the race. It's a good race though, and if you can do it, I recommend it.
Governor's Cup: A long standing, Maryland tradition. It's a lot of fun, not as painful as Down the Bay, and has a good party afterwards. I highly recommend you sign up for this one. It's a good race, and participation will help keep it alive. The finish is between the colony ship Dove and "Cross Point" on the St. Mary's River. After-party as at beautiful St. Mary's College.
Eastport to Solomons Invitational. This is another overnight race from the Annapolis vicinity to Solomons Island and is the shortest of the 3, but not too short to be boring! Also has a great after-party with music and booze at a local hotel.
All 3 races are north to south, and prevailing winds this time of year are from south to north, so expect an upwind slog (but be prepared for anything!)
Hope this helps.
Alacrity, 1981 Tartan 33 #168