| | 1 | | | Eve | SCYA | 7,825.4 | 172 | California YC | M242 Shirt Sales | | Soc | | past | Info | RSVP Closed |
| Jan 1 | 2 | Jan 1 | Sun | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Jack Roberts Memorial NYD Race | | PUR | | results | Info | Results |
| Jan 14 | 3 | Jan 14 | Sat | Day | SCYA-SD | 0.0 | 244 | SoCal YRG | Cabrillo 1 - Around the Island Race | Y | HCP | | past | Info | Reg Closed |
| Feb 08 | 4 | Feb 08 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Get together at the Sail Loft | | Soc | | past | Info | RSVP Closed |
| Feb 18,19 | 5 | Feb 18,19 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | SCYA MidWinters | | OD | | results | Info | Results |
| Feb 25,26 | 6 | Feb 25,26 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harken #1 Optimist Spring Regatta Green Fleet | | Jr | | past | Info | Reg Closed |
| Feb 25,26 | 7 | Feb 25,26 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harken #1 Optimist Spring Regatta Championship Fleet | | Jr | | past | Info | Reg Closed |
| Mar 18 | 8 | Mar 18 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #1 - The Stoney Special* | Y | HCP | SS | results | Info | Results |
| Apr 1,15 | 9 | Apr 1,15 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | HC Spring Race Days | | HCP | OS, CS | results | Info | Results |
| Apr 13... | 10 | Apr 13,20,27,May 4,11,18,25,Jun 1,8,15,22,29 | Thu | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Twilights First Half | | HCP | | results | Info | Results |
| Apr 16 | 11 | Apr 16 | Sun | Day | CBYRA | 0.0 | 570 | South Maryland Sailing Assoc. | Spring Invitational | | HCP | | results | Info | Results |
| Apr 16 | 12 | Apr 16 | Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harris Spring Regatta | | HCP | | results | Info | Results |
| Apr 19... | 13 | Apr 19,26,May 3,10,17,24,31,Jun 7,14,21,28,Jul 5,12,19,26,Aug 2,9,16,23,30,Sep 6 | Wed | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Sunset Series | | HCP | | results | Info | Results |
| Apr 22 | 14 | Apr 22 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #2 - TransHarbor Race* | Y | HCP | SS | results | Info | Results |
| Apr 22... | 15 | Apr 22,May 6,Jun 3 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Dolphin Trophy Series | | SS | OS, CS | results | Info | Results |
| Apr 26... | 16 | Apr 26,May 3,10,17,24,31 | Wed | Eve | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 1 | | HCP | | results | Info | Results |
| Apr 29 | 17 | Apr 29 | Sat | Eve | GMORA | 5,240.0 | 70 | GMORA | GMORA 2022 Awards Reception and 2023 Kick-Off | | Soc | | past | Info | RSVP Closed |
| May 7 | 18 | May 7 | Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 1 | Y | PUR | pc | results | Info | Results |
| May 10 | 19 | May 10 | Wed | Eve | MBSA | 5,251.4 | 2 | Hingham Bay Racing | 2023 Spring Meeting & 2022 Awards | | Soc | | past | Info | RSVP Closed |
| May 10 | 20 | May 10 | Wed | Eve | MBSA | 5,259.5 | 9 | Constit. YC | Constitution Yacht Club Season Kick Off | | Soc | | past | Info | RSVP Closed |
| May 17 | 21 | May 17 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Spring Series | | HCP | | past | Info | |
| May 18... | 22 | May 18,25,Jun 1,8,15,22,28,Jul 6,13,20,27,Aug 10,17,24,31,Sep 7,14,21,28 | Thu,... | Eve | GMORA-W | 5,239.6 | 71 | Portland YC | Thursday Night Races | | HCP | | results | Info | Results |
| May 20 | 23 | May 20 | Sat | Day | SCYA | 7,825.4 | 721 | Port Royal YC | Classic Regatta | | HCP | | results | Info | Results |
| May 21 | 24 | May 21 | Sun | Day | SCYA | 7,825.6 | 208 | King Harbor YC | Bud Bowl | | OD | | results | Info | Results |
| May 24... | 25 | May 24,31,Jun 7,14,21,28,Jul 6,12,19,26,Aug 2,9,16,23,30 | Wed,... | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Summer Series | | HCP | | results | Info | Results |
| May 24... | 26 | May 24,31,Jun 7,14,21 | Wed | Eve | MBSA | 5,240.3 | 47 | Satuit Boat Club | Spring Series | | HCP | | results | Info | Results |
| May 27 | 27 | May 27 | Sat | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Memorial Day Regatta | | HCP | | past | Info | |
| May 31... | 28 | May 31,Jun 7,14,21,28,Jul 5 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Spring Evening Series | Y | HCP | WNR | results | Info | Results |
| May 31... | 29 | May 31,Jun 7,21 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Spring Series - Wednesday Night Racing | | HCP | CUP | results | Info | Results |
| May 31... | 30 | May 31,Jun 7,21,28,Jul 5,19 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series I | Y | HCP | | results | Info | Results |
| Jun 1 | 31 | Jun 1 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 1 (COMBINED) | Y | OD | Spr, CHP, YCS, CHP | results | Info | Results |
| Jun 3,4 | 32 | Jun 3,4 | Sat,Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | results | Info | Results |
| Jun 3 | 33 | Jun 3 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights | | HCP | BKT, Q, SH/ | past | Cancelled | Reg Closed |
| Jun 6,... | 34 | Jun 6,13,20,27 | Tue | Eve | SCYA | 7,825.4 | 721 | Port Royal YC | June Cup - Women at the Helm | | HCP | | results | Info | Results |
| Jun 8 | 35 | Jun 8 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 2 | Y | OD | Spr, YCS | results | Info | Results |
| Jun 10 | 36 | Jun 10 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | Ovr, WE | results | Info | Results |
| Jun 10... | 37 | Jun 10,11,24,25 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Summer Series | | HCP | Ovr, PB | results | Info | Results |
| Jun 10 | 38 | Jun 10 | Sat | Eve | CBYRA-Annap | 5,495.9 | 452 | Sailing Club Chesapeake | Ted Osius Memorial Twilight Regatta | | HCP | | results | Info | Results |
| Jun 11 | 39 | Jun 11 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Somerset Regatta | | HCP | Q, SH/ | results | Info | Results |
| Jun 13... | 40 | Jun 13,20,Jul 4,11,25,Aug 1,15,22,29,Sep 12,12,12 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC | RYC Tuesday Night Series | | HCP | | results | Info | Results |
| Jun 15 | 41 | Jun 15 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 3 (COMBINED) | Y | OD | Spr, CHP, YCS, CHP | results | Info | Results |
| Jun 15... | 42 | Jun 15,22,29,Jul 6,13,20,27,Aug 3,10,17,24,Sep 7 | Thu | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Twilight Series | | OD | | results | Info | Results |
| Jun 16 | 43 | Jun 16 | Fri | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl OCS (Day Time) | | HCP | | past | Info | |
| Jun 16 | 44 | Jun 16 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #1 | | PUR | | results | Info | Results |
| Jun 16 | 45 | Jun 16 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl | | HCP | Q | past | Info | |
| Jun 17 | 46 | Jun 17 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta | | HCP | BKT, Q, SH/ | results | Info | Results |
| Jun 17 | 47 | Jun 17 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | HCP | SOS | results | Info | Results |
| Jun 17 | 48 | Jun 17 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Pilot Regatta | | HCP | Ovr, WE | results | Info | Results |
| Jun 17 | 49 | Jun 17 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #3 - The Malibu & Return Race* | Y | HCP | SS | results | Info | Results |
| Jun 18 | 50 | Jun 18 | Sun | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Constitution YC Spring Regatta | | HCP | Q, SH/ | results | Info | Results |
| Jun 23 | 51 | Jun 23 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | SH/ | results | Info | Results |
| Jun 23... | 52 | Jun 23,30,Jul 14,28,Aug 11,25 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 23... | 53 | Jun 23,30,Jul 14,28,Aug 11,25 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Division 2 Handicap Twilight Series | | HCP | | results | Info | Results |
| Jun 23... | 54 | Jun 23,24,25 | Fri,... | Day | GYA | 0.0 | 742 | GYA Challenge Cup | GYA Offshore Challenge Cup | | HCP | | results | Info | Results |
| Jun 24,25 | 55 | Jun 24,25 | Sat,Sun | Day | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | R19 East Coast Championship | | OD | | results | Info | Results |
| Jun 24 | 56 | Jun 24 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Regatta | | PUR | Ovr, WE | results | Info | Results |
| Jun 24 | 57 | Jun 24 | Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | results | Info | Results |
| Jun 25 | 58 | Jun 25 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | MYC Patton Bowl | | HCP | | results | Info | Results |
| Jun 25 | 59 | Jun 25 | Sun | Day | CBYRA-SoMD | 0.0 | 570 | South Maryland Sailing Assoc. | Summer Invitational | | HCP | | past | Info | Reg Closed |
| Jun 28... | 60 | Jun 28,Jul 5,19,26,Aug 2 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Summer Series - Wednesday Night Racing | | HCP | CUP | results | Info | Results |
| Jun 28 | 61 | Jun 28 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Summer Series | | HCP | | past | Info | |
| Jun 28... | 62 | Jun 28,Jul 5,12,19,26 | Wed | Eve | MBSA-S | 5,240.3 | 47 | Satuit Boat Club | Early Summer Series | | HCP | | results | Info | Register |
| Jun 30 | 63 | Jun 30 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | SOS | results | Info | Results |
| Jul 1 | 64 | Jul 1 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup and Classics Series #1 | | HCP | Ovr, BB | results | Info | Results |
| Jul 1 | 65 | Jul 1 | Sat | Day | MBSA | 5,240.3 | 47 | Satuit Boat Club | Scituate Invitational | | PUR | | past | Info | Reg Closed |
| Jul 1 | 66 | Jul 1 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | Schooner Trophy Race | | HCP | | results | Info | Results |
| Jul 1,... | 67 | Jul 1,8,16,23,29,Aug 5 | Sat,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE PHRF | | HCP | PB | results | Info | Results |
| Jul 1 | 68 | Jul 1 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constit. YC | Red, White + Blue Race | | HCP | | past | Cancelled | Reg Closed |
| Jul 2 | 69 | Jul 2 | Sun | Day | MBSA-N | 5,253.2 | 30 | Palmers Cove YC | Mass Bay Shorthanded Regatta | | HCP | SH/ | results | Info | Results |
| Jul 2 | 70 | Jul 2 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | July 2 Fun Race | | PUR | | results | Info | Results |
| Jul 4 | 71 | Jul 4 | Tue | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 153rd Anniversary | | HCP | Q | past | Info | Results |
| Jul 6 | 72 | Jul 6 | Thu | Day | MBSA-N | 0.0 | 101 | Manchester SA | Green Fleet Regatta for First Time Racers | | Jr | | past | Info | Reg Closed |
| Jul 6,... | 73 | Jul 6,13,20,Aug 3,10,17,24,31,Sep 7,14 | Thu | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Twilights Second Half | | HCP | | results | Info | Results |
| Jul 6,... | 74 | Jul 6,13,20,Aug 3,10,17,24,31,Sep 7,14 | Thu | Eve | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Twilights Second Half (Shadow TOT) | | HCP | | results | Info | Results |
| Jul 7,8,9 | 75 | Jul 7,8,9 | Fri,... | Day | SCYA | 7,825.4 | 172 | California YC | M242 North American Championship | | OD | | results | Info | Results |
| Jul 8,9 | 76 | Jul 8,9 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | King of Spain | | OD | | results | Info | Results |
| Jul 8,9 | 77 | Jul 8,9 | Sat,Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | King of Spain Series | | PUR | | results | Info | Results |
| Jul 8 | 78 | Jul 8 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | S.S. Crocker Memorial Race | | PUR | P | results | Info | Results |
| Jul 9 | 79 | Jul 9 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | July 9 Fun Race | | PUR | | results | Info | Results |
| Jul 9 | 80 | Jul 9 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Annual Round Southport Race | | PUR | | past | Cancelled | Reg Closed |
| Jul 11,12 | 81 | Jul 11,12 | Tue,Wed | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Battle of the Bay Junior Regatta | | Jr | | results | Info | Results |
| Jul 12 | 82 | Jul 12 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Greater Boston Rumble II | | HCP | | results | Info | Results |
| Jul 13,14 | 83 | Jul 13,14 | Thu,Fri | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham Bay Junior Regatta | | Jr | SSJ | results | Info | Results |
| Jul 14 | 84 | Jul 14 | Fri | Day | GMORA-P | 5,194.4 | 777 | Rockport BC | RBC - Paper Cup Challenge | | PUR | Ovr, PB | results | Info | Results |
| Jul 15 | 85 | Jul 15 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup and Classics Series #2 | | HCP | | past | Cancelled | Reg Closed |
| Jul 15 | 86 | Jul 15 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Gloucester Ocean Pursuit Race | | PUR | P | past | Info | Reg Closed |
| Jul 15 | 87 | Jul 15 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Casco Bay Fiasco | | HCP | Ovr, WE | results | Info | Results |
| Jul 15 | 88 | Jul 15 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup | | HCP | Q | results | Info | Results |
| Jul 16 | 89 | Jul 16 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Ocean Race | | HCP | | past | Cancelled | Reg Closed |
| Jul 16 | 90 | Jul 16 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | July 16 Fun Race | | PUR | | results | Info | Results |
| Jul 20,21 | 91 | Jul 20,21 | Thu,Fri | Day | MBSA-S | 5,250.2 | 1 | Hull YC | Hull Yacht Club Junior Scorpion Bowl Regatta | | Jr | SSJ | results | Info | Results |
| Jul 21 | 92 | Jul 21 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #2 | | PUR | | results | Info | Results |
| Jul 21,23 | 93 | Jul 21,23 | Fri,Sun | Day | MBSA | 5,251.4 | 2 | Hingham Bay Racing | Rally to the Crown | | Trial | | past | Info | Results |
| Jul 22 | 94 | Jul 22 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Solstice Race-Rescheduled | | HCP | Ovr, PB | results | Info | Results |
| Jul 22,23 | 95 | Jul 22,23 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Regatta & Shipyard Cup Classics Challenge | | HCP | Ovr, WE, PB, BB | results | Info | Results |
| Jul 23 | 96 | Jul 23 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Lindsay Smith Fast Mermaid Regatta | | PUR | | past | Info | |
| Jul 23 | 97 | Jul 23 | Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 2 | Y | PUR | pc | results | Info | Results |
| Jul 26... | 98 | Jul 26,Aug 2,16,23,30,Sep 6,13 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series II | Y | HCP | | results | Info | Results |
| Jul 28... | 99 | Jul 28,29,29 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup | Camden Classics Cup | | HCP | Ovr, WE, PB, BB | results | Info | Results |
| Jul 28 | 100 | Jul 28 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC | Downeast Challenge | | HCP | Ovr, SH/, BB | results | Info | Results |
| Jul 28... | 101 | Jul 28,29,30 | Fri,... | Day | SCYA | 7,825.4 | 172 | California YC | CFJ Nationals | | Jr | | results | Info | Results |
| Jul 29,30 | 102 | Jul 29,30 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Seniors | | OD | | results | Info | Results |
| Jul 29 | 103 | Jul 29 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Round the Salvages Pursuit Race | | PUR | P | results | Info | Results |
| Jul 29,30 | 104 | Jul 29,30 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC | Lipton Cup Regatta Juniors | | Jr | SSJ | results | Info | Results |
| Jul 30 | 105 | Jul 30 | Sun | Day | GMORA-P | 5,189.5 | 275 | Stockton Harbor SC | Turtlehead Trot | | PUR | Ovr, PB | results | Info | Results |
| Aug 2,... | 106 | Aug 2,3,3,3,3,3 | Wed,Thu | Day | GMORA-B | 5,211.2 | 147 | Southport Jr YC Sailing | 2023 Maine State Optimist Championship | | Jr | | results | Info | Results |
| Aug 2,... | 107 | Aug 2,9,16,23,30 | Wed | Eve | MBSA-S | 5,240.3 | 47 | Satuit Boat Club | Late Summer Series | | HCP | | results | Info | Results |
| Aug 4 | 108 | Aug 4 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Feeder Race | | HCP | | results | Info | Results |
| Aug 5 | 109 | Aug 5 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | HCP | Q | past | Cancelled | Reg Closed |
| Aug 5 | 110 | Aug 5 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 29th CPYC Pursuit Race to Benefit Make-A-Wish | | PUR | P | results | Info | Results |
| Aug 5,6 | 111 | Aug 5,6 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC Youth Regatta to Benefit Make A Wish | | Jr | SSJ | results | Info | Results |
| Aug 5 | 112 | Aug 5 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup and Classics Series #3 | | HCP | Ovr, BB | results | Info | Results |
| Aug 5,6 | 113 | Aug 5,6 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC RegattaTo Benefit Make-A-Wish One Design/ Snipe New England's | | OD | | results | Info | Results |
| Aug 5,6 | 114 | Aug 5,6 | Sat,Sun | Day | SCYA | 7,825.7 | 253 | Womens Sailing Association (SMB) | WOW/WAH | | HCP | | results | Info | Results |
| Aug 5 | 115 | Aug 5 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #4 - KHYC to CBYC | Y | HCP | SS | results | Info | Results |
| Aug 5,6 | 116 | Aug 5,6 | Sat,Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | results | Info | Results |
| Aug 6 | 117 | Aug 6 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R. Hodder Ocean Race | | HCP | | past | Info | |
| Aug 8,9 | 118 | Aug 8,9 | Tue,Wed | Day | MBSA-S | 5,255.1 | 53 | Winthrop YC | N-10 Open | | Jr | | results | Info | Results |
| Aug 9 | 119 | Aug 9 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Greater Boston Rumble III | | HCP | | results | Info | Results |
| Aug 9 | 120 | Aug 9 | Wed | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Maine State 420 Championships & RS Tera East Coast Championships | | Jr | | results | Info | Results |
| Aug 9 | 121 | Aug 9 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Fall Series | | HCP | | past | Info | |
| Aug 11 | 122 | Aug 11 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Summer Pursuit Race #3 | | PUR | | results | Info | Results |
| Aug 12 | 123 | Aug 12 | Sat | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Summer Regatta | | OD | | past | Info | Reg Closed |
| Aug 12 | 124 | Aug 12 | Sat | Day | SCYA | 7,825.4 | 721 | Port Royal YC | Pirate Regatta - High Point Race #8 | | HCP | | results | Info | Results |
| Aug 12 | 125 | Aug 12 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC | Flip Flop Regatta | | PUR | P | results | Info | Results |
| Aug 12 | 126 | Aug 12 | Sat | Day | GMORA-W | 0.0 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | Ovr, WE, PB, BB | results | Info | Results |
| Aug 13 | 127 | Aug 13 | Sun | Day | MBSA | 5,250.6 | 7 | Eastern YC | EYC Members Club Championship | | OD | | results | Info | |
| Aug 16... | 128 | Aug 16,23,30,Sep 6 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Fall Series - Wednesday Night Racing | | HCP | CUP | results | Info | Results |
| Aug 18... | 129 | Aug 18,19,20 | Fri,... | Day | MBSA | 0.0 | 4 | Mass Bay Sailing | Ted Hood Regatta | | HCP | Q | results | Info | |
| Aug 19 | 130 | Aug 19 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Rockland Yacht Club Scholarship Race | | HCP | Ovr, PB | results | Info | Results |
| Aug 19 | 131 | Aug 19 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Queen Mary Regatta | | HCP | | results | Info | Results |
| Aug 19 | 132 | Aug 19 | Sat | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | PBCF Cruising Fleet Double. Handed Race | | PUR | | results | Info | Results |
| Aug 19 | 133 | Aug 19 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Bluewater Regatta | | HCP | Ovr, WE | results | Info | Results |
| Aug 19 | 134 | Aug 19 | Sat | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Commodore's Cup and Classics Series #4 | | HCP | Ovr, BB | results | Info | Results |
| Aug 19 | 135 | Aug 19 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC | Hingham YC Hitchcock Trophy | | HCP | BKT, Q | results | Info | Results |
| Aug 23... | 136 | Aug 23,30,Sep 6,13,20,27 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Fall Evening Series | Y | HCP | WNR | results | Info | Results |
| Aug 26 | 137 | Aug 26 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Cape Ann Challenge | | HCP | | past | Info | Results |
| Aug 26 | 138 | Aug 26 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Windward Leeward Regatta | | HCP | | past | Cancelled | Reg Closed |
| Aug 27 | 139 | Aug 27 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | HCP | Ovr | results | Info | Results |
| Aug 27,27 | 140 | Aug 27,27 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 38th Annual JFK Regatta - A Mass Bay Qualifier | | HCP | | results | Info | Results |
| Aug 27 | 141 | Aug 27 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | P | results | Info | Results |
| Aug 30... | 142 | Aug 30,Sep 6,13,20,27,Oct 4 | Wed | Day | CBYRA-NOTB | 5,496.9 | 602 | Rock Creek Racing | WNR Series 4 | | HCP | | results | Info | |
| Sep 1 | 143 | Sep 1 | Fri | Eve | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Once in a Blue Moon regatta and Fun Race | | PUR | | past | Info | Reg Closed |
| Sep 2 | 144 | Sep 2 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Bobby Veltman Memorial Race | | HCP | | results | Info | Results |
| Sep 3,... | 145 | Sep 3,10,17,24,Oct 1 | Sun | Day | MBSA-S | 5,240.3 | 47 | Satuit Boat Club | Fall Sunday Series | | HCP | | results | Info | Results |
| Sep 4 | 146 | Sep 4 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sail Salem Pursuit Race | | PUR | | past | Info | |
| Sep 6,... | 147 | Sep 6,13,20,27,Oct 4 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Fall Series | | HCP | | results | Info | Results |
| Sep 9 | 148 | Sep 9 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup | | HCP | BKT, Q, SH/ | results | Info | Results |
| Sep 9 | 149 | Sep 9 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | Q | results | Info | Results |
| Sep 9 | 150 | Sep 9 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr, WE, PB, BB | results | Info | Results |
| Sep 9 | 151 | Sep 9 | Sat | Day | MBSA-S | 5,240.3 | 47 | Satuit Boat Club | Chowder Cup | | HCP | | results | Info | Results |
| Sep 10 | 152 | Sep 10 | Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Pacific Cup Deepwater Series Race 3 | Y | PUR | pc | results | Info | Results |
| Sep 13 | 153 | Sep 13 | Wed | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Cruising Championship | | PUR | | results | Info | Results |
| Sep 13 | 154 | Sep 13 | Wed | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | King of the Hill | | PUR | | results | Info | Results |
| Sep 16 | 155 | Sep 16 | Sat | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | PBYC Big Mouth Regatta Cruising Fleet | | PUR | | results | Info | Results |
| Sep 16 | 156 | Sep 16 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #5 - The Matt Walsh Race* | Y | HCP | SS | results | Info | Results |
| Sep 16,17 | 157 | Sep 16,17 | Sat,Sun | Day | GMORA | 5,239.5 | 85 | Etchells Fleet 27 @ Portland YC | Lobster Bowl Regatta | | OD | | past | Info | Reg Closed |
| Sep 16 | 158 | Sep 16 | Sat | OvrNt | GMORA-P | 5,192.9 | 74 | Rockland YC | Maine Rocks | | HCP | | past | Cancelled | Reg Closed |
| Sep 17... | 159 | Sep 17,23,Oct 8,15,Nov 12,18 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | OF, CF | results | Info | Results |
| Sep 17 | 160 | Sep 17 | Sun | Day | MBSA-S | 5,250.2 | 1 | Hull YC | HYC Great Chase Race | | PUR | P | results | Info | Results |
| Sep 17 | 161 | Sep 17 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | Manchester Fall Series | | HCP | Q | results | Info | Results |
| Sep 23... | 162 | Sep 23,30,30,Oct 7,14 | Sat | Day | GMORA-W | 5,239.6 | 71 | Portland YC | The Fall Series | | HCP | Ovr, WE | results | Info | Results |
| Sep 23 | 163 | Sep 23 | Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | P | results | Info | Results |
| Sep 23 | 164 | Sep 23 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti Team Race | | Soc | | past | Info | RSVP Closed |
| Sep 24 | 165 | Sep 24 | Sun | Day | MBSA | 5,250.6 | 7 | Eastern YC | Marblehead Chowder Cup Challenge | | HCP | Q | results | Info | Results |
| Sep 29 | 166 | Sep 29 | Fri | Eve | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Harvest Moon Race | | PUR | | past | Info | Reg Closed |
| Sep 30 | 167 | Sep 30 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | Community Sailing Race Week Handicap Classes | | HCP | OF, CF, OF | results | Info | Results |
| Sep 30 | 168 | Sep 30 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | P | results | Info | Results |
| Oct 1 | 169 | Oct 1 | Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Shadden Series #2 | | OD | | results | Info | Results |
| Oct 1 | 170 | Oct 1 | Sun | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | His N Hers Regatta #1 | Y | HCP | MCM, HnH | results | Info | Results |
| Oct 1 | 171 | Oct 1 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Bandit Race - Short Handed | | HCP | SH/ | results | Info | Results |
| Oct 7 | 172 | Oct 7 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Castillon Classic | | HCP | | results | Info | Results |
| Oct 8 | 173 | Oct 8 | Sun | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | His N Hers Regatta #2 | Y | HCP | MCM, HnH | results | Info | Results |
| Oct 22 | 174 | Oct 22 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday Fun Race | | PUR | | past | Info | Reg Closed |
| Oct 22 | 175 | Oct 22 | Sun | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | His N Hers Regatta #3 | Y | HCP | MCM, HnH | results | Info | Results |
| Nov 11 | 176 | Nov 11 | Sat | Eve | GMORA | 5,240.0 | 70 | GMORA | 2023 GMORA Annual Fall Meeting and Awards Reception | | Soc | | past | Info | RSVP Closed |
| Nov 12 | 177 | Nov 12 | Sun | Eve | MBSA | 5,259.5 | 9 | Constit. YC | CYC Annual Meeting and Brunch | | Soc | | past | Info | RSVP Closed |
| Nov 17 | 178 | Nov 17 | Fri | Eve | MBSA | 0.0 | 4 | Mass Bay Sailing | MBSA Awards Celebration | | Soc | | results | Info | RSVP Closed |
| Nov 25 | 179 | Nov 25 | Sat | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Saturday Fun and PYC bar reopening race | | PUR | | past | Info | Reg Closed |
| Dec 2 | 180 | Dec 2 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Christmas Regatta | | HCP | | results | Info | Results |
| Jun 12 | 181 | Jun 12 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constit. YC | Greater Boston Rumble I | | HCP | | past | Cancelled | Reg Closed |