Popular July Sailboat Races on the Chesapeake

Sailboat Racing Anyone?

What do racing sailors do in July on the Chesapeake? They race and race and race. If you’re having trouble deciding which regattas to sign up for, below find a list of tried and true events to consider. Find more racing events on our calendar.

screwpile sailboat racing
Racing sailors during a breezy Screwpile Lighthouse challenge Regatta. Photo by Will Keyworth

BCYA Race to Baltimore: July 20

Truly a "Race to Baltimore,” an anticipated 50-plus sailboats in at least 10 divisions will rendezvous at Baltimore Light near the mouth of the Magothy River. Sponsored for the last 37 years by the Baltimore City Yacht Association, this CBYRA sanctioned race has been one of the main events of the summer sailing season. Weather conditions permitting, the race committee will attempt to run at least a 20-mile race.

The after-race party will be held at Anchorage Marina, 2501 Boston St., Baltimore MD 21224. Register through BCYA today.

FBYC Annual One Design Regatta: July 20-21

When a regatta takes place 85 times, you know there’s something special about it! This is the 85th edition of Fishing Bay YC’s One Design Regatta. Expected classes are the Flying Scot, ILCA (6 & 7), Melges 15, Hampton One Design, Isotope, Weta, Albacore, Optimist (Red, Blue, White and Green fleets) & Portsmouth Handicap. Come down to Deltaville, VA, for two fantastic days of OD Racing on the Chesapeake Bay. More than 100 boats are expected. Find more here.


HHSA Women's Regatta is a joy for racing sailors... it takes place in July rather than June this year. Photo by Will Keyworth

Herrington Harbour Women’s Regatta: July 13

Women skippers and crew are preparing for the 2024 HHSA Women's Regatta. Due to the overwhelming number of sailors who are participating in either the Annapolis to Bermuda or Newport to Bermuda races this year HHSA has moved the regatta from June to July. 

The regatta is one of the few events on the Chesapeake Bay that is for just women sailors. It's a wonderful one-day, three-race regatta with all women skippers and crew. This event is for experienced and novice racers. The regatta’s mission is that everyone steps up and does something they haven't done before. Maybe you've raced but never skippered; maybe you're a cruiser and haven't raced. Sign up and join the fun.

Screwpile Regatta: July 19-21 

That’s right, three days! There aren’t many three-day regattas left on the Bay, are there? Racing sailors at Southern Maryland Sailing Association and from across the Bay welcome the Screwpile Lighthouse Challenge Regatta. With a rich tradition of competitive racing and being centrally located in the Chesapeake in Solomons, MD, Screwpile is in its 33rd year.

Screwpile racers will be happy to know that the Solomons Inn Resort & Marina (ex-Holiday Inn), once the regatta’s go-to residence for countless Screwpile crews, will be open and back in business after a year’s closure. The new owners are racing the clock and have committed to having the hotel open for Screwpile race crews by July 15. At the time of this writing, the hotel’s manager is finishing up the reservation process and will have word out on details by the time you read this. Discounted rooms, an open pool, and complimentary breakfast will be ready in time for Screwpile.

SPLC will offer three days of racing on two courses: One design and PHRF on windward/leeward circle and government marks middle-distance for CRCA Cruisers. In addition, Screwpile will host the PHRF of the Chesapeake Northern Bay Championships again this year. Register at screwpile.com or on the Yachtscoring page.  

SSA’s Olivia Constants Team Race Invitational: July 20-21

This regatta, now in its 11th year, is So. Much. Fun. Sailors of all skill levels and ages are welcome to this team race regatta in the spirit of Olivia to benefit the Olivia Constants Foundation . More info here.