Some of the best racing on the Bay is coming up quickly, so make sure you’re registered and have crew lined up before things get busy (unacceptable excuses include spectating children’s soccer games, regular lawn maintenance, and anything to do with Ikea).
Screwpile Lighthouse Challenge : July 17-19
Register for southern Maryland’s perennial all star regatta, held at Solomons Island, which promises parties just as good as the racing. Also, join us there for a celebration of Spinsheet’s 20th birthday!
Poplar Island Race : July 18
A distance race held out of West River Sailing Club.
Race to Baltimore : July 18
One of the more popular distance races in the Chesapeake Bay area, from the Magothy River to Baltimore’s Inner Harbor. It offers multiple classes, good parties, great racing, and tons of fun!
Star Spangled Classic : July 19
Held by the Rock Creek Racing Association, this regatta serves as a “Race Back” for the Race to Baltimore participants and for boats leaving Baltimore and heading back to the bay.
Windmill Class National Championship : July 24-26
Looking for a fun, yet challenging, small-boat event this summer? Look no further! The Windmill class will be hosting their national championship out of Rock Hall Yacht Club. The Windmill is a 15 and 1/2 foot high performance racing dinghy designed by Clark Mills in the 1960’s. This boat can accommodate the skill sets of a novice sailor to an olympian, and provides an immense amount of fun. We’re always looking for new sailors! There are already 28 boats registered to sail- you could be next!
Sippy Cup/ Big Gulp Regatta : July 31
Hosted by Walden Rigging, this is a “for fun” race encouraging small boats and everyone else to experience the challenges and beauty of sailing at night.
Governor’s Cup Yacht Race : July 31- August 1
Held July 31st and August 1st, the Governor’s Cup Yacht Race is the oldest and longest overnight race on the Chesapeake Bay. This year marks the 42nd running of the race from Maryland’s current capital city to its first capital in St. Mary’s City.
Annual Oxford Regatta : August 8-9
Tred Avon Yacht Club’s largest annual regatta with racing for PHRF, Log Canoes, Stars, Comets, Snipes, Penguins, Optis, Lasers, and Club 420’s. Fun sailing for small and big boats alike!
Leo Wardrup Memorial Cape Charles Cup : August 15-16
Registration is underway for the Broad Bay Sailing Association’s signature event of the summer- The Cape Charles Cup. The only “destination” weekend regatta on the Southern Bay, it has plenty of racing competition, plus two “signature parties” highlighted by the Saturday post-race festivities at The Oyster Farm Marina at Kings Creek. At this regatta, there is truly something for everyone!
Boatyard Bar & Grill Regatta for CRAB : August 22
Held out of Eastport Yacht Club, this regatta benefits CRAB- Chesapeake Area Accessible Boating, a non-profit organization dedicated to making sailing available for people with disabilities. It is both a family-friendly, no-pressure regatta, as well as a good tune-up for Annapolis Race Week.
Olivia’s Team Race Invitational : August 22-23
A regatta dedicated to Olivia Constance, and hosted by her foundation out of SSA, this team race regatta is like no other- unlike other team racing regattas, Olivia’s regatta requires only that you bring a skipper and crew, no boats! The regatta is open to all, regardless of age, skill and club affiliation.
