Racing Calendar 2020

Top Racing Events To Put on Your 2020 Calendar

This is NOT a complete Chesapeake Bay sailboat racing calendar, but rather a rough list to help you plan your schedule; it’s (mostly) based on larger big-boat regattas. The CBYRA-sanctioned events have now been added (as of Feb. 11). Send updates to [email protected].

The list below is for the mid- to upper Bay. Find the Southern Bay racing calendars North division here and South division here

If you seek dinghy racing events, it’s best to keep your eyes on individual club websites—for example, Severn Sailing Association will host events almost every weekend in season!

April 11          Naval Academy Sailing Squadron Spring Invitational

April 19          SMSA Annual Spring Regatta

April 19-Oct 18  (Sundays) WRYC Ware Yacht Club       Albacore Races 

April 22           AYC Wednesday Night Races

April 23-26     Solings North American Championships

April 25-26     Hampton Yacht Club Spring Fling

May 2              SCC Spring Race

May 2-3           Viper 640 Mid-Atlantics

May 3              AYC Spring One Design

May 9              Annapolis YC Spring Oxford Race

May 9              AYC Spring Harbor Regatta

May 15-17       Helly Hansen Annapolis NOOD Regatta (it’s also the beginning of USNA Commissioning Week!)

May 22            Down the Bay Race

May 23            Miles River Race

May 24            EYC Miles River Race Back

May 29-31       Southern Bay Race Week

May 30            Leukemia Cup

June 5              Mustang Survival Annapolis to Bermuda Race

June 6              Don Backe Memorial CRAB Regatta

June 6              CHESSS Poplar Island Race

June 6              PSA Moonlight Race

June 12-14      Hampton Yacht Club 505 East Coasts 

June 13            NERYC Invitational

June 13            SCC Twilight Race

June 14            SMSA Summer Invitational

June 19            Newport Bermuda Race

June 19            BCYA Summer Sailstice Regatta

June 21            Ted Osius Memorial Regatta

June 24-28       Snipe U.S. Nationals

June 27            Eastport YC One Design Invitational

June 27             Herrington Harbour Sailing Association Women's Regatta

June 27-28       GSA Northern Bay Regatta

June 30            AYC Junior Annual

July 11             Eastport YC Boomerang Race

July 11-12        Hampton YC Annual

July 18             BCYA Race to Baltimore

July 19             RCRA Star Spangled Classic

July 25            Corsica River YC Annual One-Design Regatta

July 25              HYC Hampton Yacht Club     Bow ties-OD     

July 25-26       AYC Annual Regatta

July 30             Indian Landing Boat Club Annual Regatta

July 31            St. Mary’s College Governor’s Cup

Aug 1-2           WRYC Ware Yacht Club         Virginia’s Gov’s 

Aug. 7             Race to Oxford

Aug. 8-9          Tred Avon YC Oxford Regatta

Aug. 15           CRAB Cup

Aug. 15-16      Cape Charles Cup

Sept. 4-6          FBYC Stingray Point Regatta

Sept. 5-6          Annapolis Labor Day Regatta

Sept. 12           NASS Oxford Race

Sept. 13           TAYC Hammond Memorial Race

Sept. 19           Hospice Cup

Sept. 23-26      Shields Nationals

Sept. 25           AYC 3-2-1

Sept. 26           AYC Fall Race to Solomons

Sept. 26            Havre de Grace YC Fall Invitational Heffner Memorial

Sept. 27             Cove Point Classic Regatta

Sept. 27-28      SMSA Screwpile Lighthouse Challenge

Oct. 3                Cambridge YC Admiral Byrd Regatta

Oct. 3                 PSA Race to Rock Hall

Oct. 3-4           AYC Doublehanded Distance Race

Oct. 3-4, 10, 17-18      AYC Fall Series

Oct. 10                  GSA Frigid Digit

Oct. 19                 Shearwater SC Good Old Boat Regatta

Oct. 15-18             Melges 24 US National Championship (TAYC)

Oct. 17                      BCYA Harbor Cup (CBYRA SAYS NO DATE? BCYA says this is it. Stay tuned!) 

Oct. 18                       RCRA Francis Scott Key Classic

Oct. 18                     SMSA Fall Invitational

Oct. 24                    AYC Fall Etchells/ Lippincott/ Halloween Howl
Oct 24                     HYC Hampton Yacht Club Viper Day

Oct. 29-Nov. 1             J/105 North Americans & J/111 NAs (AYC)

Nov 7-8                HYC Hampton Yacht Club Fall Fling 
Nov. 8                          AYC Frostbite Racing 1st half

Keep this page bookmarked, as we will update it and enter links as the season unfolds. Find more racing news here.

Missed racing photos from 2019? Link to last year's photos here