The Chesapeake Bay region’s “Triple Crown of Charity Sailing” sets sail, raising funds and awareness for special causes
Sailboats of various classes compete in the Triple Crown of Charity Sailing races on Chesapeake Bay waters.
The Triple Crown Sailing Trophy is a refurbished trophy, by Weems & Plath, with origins dating back to the 1930s.
The sport of sailing is vibrant throughout the Chesapeake Bay. Our waters are populated by a wide variety of boats for racing, cruising, day sailing, fishing, kayaking, paddle boarding, rowing, power boating, and vessels for tourists. Every person heads out to the water for the freedom of being away from land, connecting with nature, enjoying time with family and friends, and for some, testing one’s competitive skills. All of us who sail are lucky.
In that spirit many sailors are inspired to help others to spend time on the water or support important causes outside the sport of sailing. Since 2018, several sailing events have been organized as “charity regattas” with three of the biggest and most widely supported in the region combined into the Triple Crown of Charity Sailing. Success in these events is measured in two ways:
1. Good finishes on the racecourse.
2. The amount of money raised by individuals and teams of sailors.
The competition is spirited in both categories. The Hospice Cup was created in 1981 by Albert G. Van Metre, the owner of the famous ocean racer, Running Tide. Meredith Glacken is the Executive Director of the 2025 edition of the Hospice Cup. She reports, “The 2024 Hospice Cup was the most successful in 25 years. Nearly 90 boats competed together with sponsors raising more than $200,000.”
In 1993, the Eastport Yacht Club responded to a request by the Leukemia Society to host a charity sailboat race. The event in June of that year attracted over one hundred boats and raised $30,000. The event was renamed Maryland Cures Cancer Regatta in 2022.
Sailboats of various classes compete in the Triple Crown of Charity Sailing races on Chesapeake Bay waters.
The most recent regatta to be created is the CRAB Cup for Accessible Boating. In 2024, an impressive total of 102 boats participated in a pursuit race, where the slowest boats start first, and the fastest boats start last. CRAB was founded in 1991 for by the late Don Backe (1936–2013) who was disabled as an adult in an automobile accident. The CRAB Cup also includes powerboats in a poker pursuit race where participants motor to different locations on the Bay and take a selfie photograph. The goal is to complete a five-card poker hand.
A total of 251 boats and well over 1,000 sailors participated in 2024 edition of the Triple Crown. The three events raised $572,000 for the three charities. Paul “Bo” Bollinger, the Executive Director of Chesapeake Regional Accessible Boating (CRAB), reports, “In 2024 the CRAB Cup raised $250,000. The funds support CRAB’s sailing programs, fishing, radio- controlled sailing, and therapeutic programming. All programs are provided free of charge to our guests with disabilities, wounded warriors, and children from underserved communities. CRAB teaches sailing to approximately 1,200 guests on our fleet of six Beneteau First 22A’s.”
The Maryland Cures Cancer Regatta (formerly Leukemia Cup) has raised over $3 million in Maryland alone since its founding in ’93. From then until 2020, over forty Leukemia Cup regattas took place annually across the United States, raising about $66 million overall. Then, in 2020, during the Covid-19 Pandemic, the Leukemia & Lymphoma Society decided to withdraw from sponsoring fundraising sailing regattas. Yet, the Eastport Yacht Club had been a leader of the event in the Chesapeake region and served as an example of how to be effective. So, in 2022 EYC decided to resume the regatta, rename it, and use the donated funds to support a new Cancer Center currently under construction at the University of Maryland Medical Center in Baltimore.
Bill Levatino and Andy Guhl are co-chairs of the race committee of the Cancer Cup. Guhl says, “We had 75 boats last year and raised $68,000. The Triple Crown helped us attract entries. One (event) feeds into the next. It has given us a more positive impact than if we did it on our own. To expand our participation, the Eastport Yacht Club teams up with the Annapolis Yacht Club, the Rock Creek Racing Association, Harrington Harbor Sailing Association, and the Maryland Yacht Club.”
Triple Crown Award winners John Dodge and the crew from Kobayashi for the Cure.
The Triple Crown of Charity Sailing concept was started by Bo Bollinger who asked Peter Trogdon—at the time the owner of Weems & Plath—to sponsor the trophy. Trogdon found a spectacular, but unused trophy from the 1930s, that was once called the Power Squadron of Baltimore Navigation Trophy. He revitalized the trophy to become the Triple Crown in 2018.
Weems & Plath continues to be the presenting sponsor. Many other local businesses, individuals, and nonprofits support the Triple Crown. The trophy is on permanent display at the new CRAB Adaptive Boating Center (ABC) at the entrance of Back Creek. And the trophy is showcased during the regattas at the Eastport Yacht Club during the Cancer and Hospice regattas. The top fundraisers have their names engraved on the trophy.
The shore parties of all three charity sailing races are lively and well-attended events, raising critical funds for local nonprofits.
Drew Fleming of Weems and Plath and Paul Bollinger (at podium) of CRAB announce last year’s Triple Crown of Charity Sailing award
Trogdon says, “I’m thrilled the events have gotten traction and momentum. The Triple Crown concept has boosted the fundraising and participation of all three events. It’s good for the sport. Bo (Bollinger) came up with the concept.”
The three regattas are spread throughout the summer months, so they do not conflict with each other. The Maryland Cures Cancer regatta is scheduled for June 14, 2025, the CRAB Cup is scheduled for August 16, 2025, and the Hospice Cup will be held on September 13, 2025. The goal is to encourage sailors to participate in all three events.
John Heinz is the Fleet captain of the popular Harbor 20 fleet in Annapolis. The Harbor 20s are active participants in all three Triple Crown Regattas. He was the highest individual fundraiser in 2018 and 2022. In 2023, he tied for the award with Tracey and Warren Richter. Heinz is enthusiastic about the series. “These charity regattas have been an important part of the Harbor 20 Fleet’s calendar since the fleet was created in 2011,” he says. “We’re proud to support these regattas, and we have fun doing it.” The 2024 winner was John Dodge and Team Kobayashi for a Cure.
Dodge performed well in the racing as well as being the top fundraising crew bringing in over $38,000. Roger Mason was the top individual fundraiser at $33,000 and was awarded the inaugural (well-named) Rainmaker trophy by Weems & Plath.
All three regattas feature creative ways to encourage participation. The Cancer Cup hosts a spirited party after racing at the Eastport Yacht Club. Guhl says the party alone raised a net of $17,000. The Hospice Cup partners with the Maryland Federation of Art to sponsor a local art competition that is open to the public. The winning piece of art that reflects the spirit of the regatta is chosen as the featured artwork for the year and appears on posters, the event website, and printed materials. The CRAB Cup hosts a year end awards ceremony where the Weems & Plath trophy is presented.
Glacken adds, “We all work together to encourage participation in each organization’s regatta starting with a Triple Crown kickoff party in the spring. The Weems & Plath trophy is a wonderful incentive, so we work hard to make sure every sailor in the region knows about it, puts three races on their calendar, and opens their checkbook.
Learn more about each organization and the Triple Crown of Charity Sailing at the following websites: eastportyc.org/mdcurescancer, crabsailing.org/crabcup, and hospicecup.org.
Gary Jobson is a world-class sailor, television commentator, author, longtime resident of Annapolis, and pre-eminent ambassador for sailing of the United States. He either serves on or has served on the boards of Operation Sail, US Sailing, Olympic Sailing Committee, Annapolis Yacht Club, National Sailing Hall of Fame, Chesapeake Bay Trust, and Visit Annapolis, among many others.
