1973: The first of several annual four day cruises to Elizabeth City took place in May.
1974: Year round one design racing was in vogue with the arrival of single handed Force 5s, Lasers, and El Toros, to join the ever popular Sunfish. Winter attire for the well dressed skipper was a wet or dry suit. The first of what were to be twelve annual Trash Bowl Regattas was held on Lake Trashmore on New Years Day.
The Cape Henry Cup Race for Cruising and MORC boats (now PHRF) was established. This is one of the more popular races on the southern Chesapeake, with the course passing out through the Maryland Channel opening of the Chesapeake Bay Bridge-Tunnel and returning through the Thimble Shoal Channel opening.
BBSA received the CBYRA One-Design Race Committee of the Year Award, and again in 1980.
1976: Membership rose to 156 families of which 95 were Cruisers or Cruiser/Racers, and 61 One-Designers. The association became affiliated with PHRF.
1977: The “NEXT TO THE LAST CAPE CHARLIE RACE” was sailed, followed in 1978 by the “2nd TO THE LAST CAPE CHARLIE RACE”. This race where kids and cats and turtles in the crew receive plus handicaps, and age and males minus handicaps, was followed by a raft-up, party, and awards? presentation. Regrettably 1997’s “2nd TO THE LAST CAPE CHARLIE RACE” became “THE LAST CAPE CHARLIE RACE”.
1986: The Association took over responsibility for the Chesapeake Light Race, later called the Chesapeake/Atlantic Race, which was a benefit race for the “The Old Coast Guard Station”. This race was discontinued in 2001, but reinstated in 2004 as the Neptune’s Atlantic Regatta.
1992: Thursday Night Racing on Willoughby Bay became a BBSA undertaking. The races are informal, with three series being held from April through September. (This BBSA organization is now known as the “Willoughby Racers”.)
1994: The “Little Creek Sailing Association”, a group of Little Creek based sailors who race informally on Wednesday evenings, came under the BBSA umbrella.
The “Little Bay Challenge” was inaugurated in conjunction with the Portsmouth Boat Club. This became a major event with over 50 “big boats” racing on Little Bay at Willoughby Spit, followed by a massive party. The Little Bay Challenge was discontinued after 2014’s race.
1996: The Little Creek Sailing Association, with the assistance of Di Ricks and other BBSA members, inaugurated the “Little Creek Cup”, a race for the benefit of the American Cancer Society. Commencing in 2001, St. Jude Children’s Research Hospital became the beneficiary of this race. In 2007, St. Jude expanded the affair to include other events, creating the Hampton Roads Regatta. 2009 was the last year of the regatta. Over the 14 year life of the event, over $1 million was raised in the fight against cancer.
2004: BBSA stepped up their PHRF racing program with the addition of two races: the Cape Charles Cup, a two day point-to-point race to Cape Charles and back which has quickly become one of the favorite races in the Southern Bay, and the Neptune's Atlantic Regatta, which is sailed from Little Creek to the Virginia Beach oceanfront in conjunction with the Virginia Beach Neptune Festival. These, in addition to the Cape Henry Cup, the Little Bay Challenge (ceased after 2014), and the Little Creek Cup (ceased after 2009), brought the total number of BBSA's major regattas up to five. This was also the inaugural year of the Southern Bay Distance Racing Series which awards trophies for best overall performance in (presently) thirteen distance races hosted by BBSA, HYC, CCV, and OPCYC. The organization and scoring of this series is administered by BBSA.
2015: The Cape Charles Cup is renamed the Leo Wardrup Memorial Cape Charles Cup to honor Leo for his efforts in reinstating one of the Southern Bay’s Premier Regattas. The 2016 edition hosted a record 90 sailboats in 9 different classes.
2016: BBSA inaugurated the Broad Bay Sailing Championship. This intramural race puts team bragging rights on the line between the Willoughby Racers, the Little Creek Sailing Association, and at-large BBSA members. 23 boats raced and the Willoughby Racers took home the first team trophy.
2017: The Hobie Fleet 32 Racing Organization is incorporated within the Broad Bay Sailing Organization One Design Fleet, returning the association to its small boat roots.
2019: BBSA Officially added a new position to the Officers of the Association, Training Officer. The first member to be elected to this position was Randy Goodman who successfully initiated the position with a variety of well attended training workshops. BBSA now offers a broad slate of training seminars and workshops in the offseason to keep its members and others in the local sailing community educated and engaged.
2020: The COVID-19 Year, where due to the Pandemic we held no in person meetings and the Cape Charles Cup was not sailed to Cape Charles and the Neptune Regatta raced to the Ocean Front with no Neptune Festival on its shore. Other on water events were still held, but with significant restrictions and precautions in place.
2023: The BBSA Constitution and By-Laws were amended in a vote at the May membership meeting. The most substantial changes include allowing the use of electronic voting of new officers and during other votes; redefining "Honorary Membership"; and changing the title of the "Rear Commodore" to "Past Commodore".