The young people we serve need support to create a good life. Many have had issues with law enforcement, some have not succeeded in school, and many may suffer from anxiety or depression. Our apprentices need a nurturing environment to learn, grow, gain confidence, and build a path toward self-sufficiency and success. Seaport’s curriculum, adult mentoring, community support, and career exploration give our Apprentices the positive environment they need.
2025
With heartfelt thanks to all who have supported the mission of the Great Chesapeake Bay Schooner Race
Total Raised $72,333.19
See past results at the bottom of this page.
Norfolk Rebel supporting GCBSR Race Events - $12,477.73
![]()
The “Tugantine” Norfolk Rebel is the first designed and built Sail Assisted Tugboat. Capt. Lane Briggs had her designed and built to be a multipurpose tug for his Marine Towing/Salvage/Construction business. Launched May of 1980. Being sail assisted, she would be able to save upwards of 30% fuel savings. In addition to towing barges and salvaging, she also towed several schooners and Tall Ships up and down the east coast. Also, she would participate in Tall Ship Festivals. Capt. Lane was also the founder of The Great Chesapeake Bay Schooner Race. His dream of schooners racing down the bay started with the first race in 1990. Bringing Schooners and their crews together to share stories of their season. The race evolved into a fundraising event every year to bring awareness to the bay. Capt. Lane passed away in September 2005, but the Norfolk Rebel is still Racing to Save the Bay by racing for The Great Chesapeake Bay Schooner Race.
Lady Maryland supporting Living Classrooms Foundation - $8,476.71

The pungy schooner Lady Maryland, educational flagship of the Living Classrooms Foundation, has been sailing the waters of the Chesapeake Bay for the past 40 years and has participated in nearly every Great Chesapeake Bay Schooner Race. During the Race, students aboard Lady Maryland work side by side with the crew to stand watch, navigate, steer and handle sail. This year we look forward to sailing the race with students from Baltimore City College HS.
During the school year, Lady Maryland can be found on the Patapsco River running day-sail programs with students from a variety of backgrounds and economic means. During our Maritime Environmental STEM Voyages, students work together to trawl for marine life, perform scientific experiments and explore the commerce, history, natural resources, and ecosystems of the Chesapeake Bay. During the summer, Lady Maryland takes students on extended voyages, sometimes venturing as far north as Massachusetts.
This year, Living Classrooms celebrates 40 years of disrupting the cycle of poverty and helping our communities in Baltimore and Washington, DC become safer, stronger, and healthier. Funds raised for the Living Classrooms Foundation will support Maritime Education programs for youth.
Jolly Dolphin supporting Magothy River Association - $7,837.96

Jolly Dolphin is a wooden sailing vessel modeled on early Chesapeake Bay oyster dredgers. Referred to as a “three sail bateau,” or “two-masted skipjack,” it is a successor to the bugeye. Jolly Dolphin was built for a Delaware family for recreational use by James B. Richardson on LeCompte Creek, Maryland in 1958. From 1964 until 2007 she passed through the hands of a half dozen owners, and was abandoned ashore in 2004. Restored with the help of the Richardson Maritime Museum from 2007 to 2010, privately owned and maintained Jolly Dolphin has provided traditional sailing experiences for community outreach. Over the years Jolly Dolphin‘s passengers have including middle school and high school STEM students, conservationists and Maryland history enthusiasts. She is currently berthed on the Magothy River.
Jolly Dolphin is proud to be sailing this year on behalf of the Magothy River Association, an organization that supports conservation and education on her home waterway. Magothy River Association works for the preservation and improvement of the water quality, plants, and wildlife of the Magothy River and its watershed. The organization’s efforts include a comprehensive oyster program that includes an oyster nursery, reef restoration, and a dive program to monitor oyster populations.
Eleanor supporting The Landing School - $6,737.06

The Schooner Eleanor , launched in May 1999, was built in Kennebunkport by Captain Rich Woodman and a crew of local craftsmen to the lines of L. Francis Herreshoff’s 1935 Mobjack design. Although her hull was constructed using modern techniques, the Eleanor is in every other way a traditional gaff-rigged schooner. Spruce spars, mahogany transom, locust rails and hand carved trail boards all contribute to the beauty of this vessel. Flying four sails with a large teak cockpit and spacious cushioned cabin tops to stretch out on, the Eleanor will give you the feel of yachting in the 1930s. Captain Rich shares his grandfather’s passion for boatbuilding and carries on this tradition in the off-season by restoring and building custom wooden boats at his boat shop in Kennebunk. He has also taught wooden boat construction at the Landing School.
Schooner Eleanor is raising funds for the Landing School of Boatbuilding and Design in Arundel, Maine. The Landing School is a leader in boatbuilding and design and has prepared graduates for a wide range of positions in the marine industry since 1978. Students build skills and knowledge through a combination of innovative classroom instruction, faculty mentorship, engagement with industry leaders, and project work. The Landing School offers eight-month diplomas in Wooden Boatbuilding, Composite Boatbuilding, Marine Systems, Yacht Design, and Boatyard Management, as well as a two-year associate degree. Students from around the world come to The Landing School from diverse personal and professional backgrounds and each class includes recent high school and college graduates, career changers, veterans, and retirees.
Pride of Baltimore II supporting Pride of Baltimore Inc. - $6,482.99
![]()
Pride of Baltimore II is an historically-evocative reproduction of the Baltimore Clipper style vessels made famous during the War of 1812. Capturing public imagination through unique worldwide voyages of discovery, Pride II honors Maryland seafarers of all eras and, wherever she sails, shares the innovation, entrepreneurial spirit, and patriotism that forged and continues to define Maryland’s maritime identity. Since her commissioning in 1988, Pride II has sailed over 275,000 nautical miles and visited more than 200 ports in 40 countries. Her mission is to promote historical maritime education, foster economic development and tourism, and represent the people of Maryland in every port she visits.
This year, Pride of Baltimore II raced to raise funds for Spanish–English educational sails to help break down language barriers, share the Chesapeake Bay’s rich maritime history, and inspire underrepresented youth and adults to explore careers on the water.
Adventurer supporting GCBSR Education Grants - $5,685.78

Adventurer and Duncan Hood have been “Racing to Save the Bay” in the Great Chesapeake Bay Schooner Race (GCBSR) since 1998, and participating in the Virtual Race since its inception.
Adventurer raised funds for GCBSR educational programs designed to further our goals of encouraging preservation of the Bay’s resources and educate kids and adults regarding the importance of schooners and sailing craft in the development of our country.
Virginia supporting Nauticus Foundation - $5,069.55

Schooner Virginia serves as a vital education platform for the Nauticus Foundation, engaging the Hampton Roads community through transformative maritime and hands-on learning experiences for students of all backgrounds and ages, museum visitors, and the general public. Funds raised during the race directly support community-based sailing experiences for students, public programming, and maintenance efforts that ensure Virginia is ready to represent Norfolk and the Commonwealth at one of the largest tall ship gatherings in decades.
Virginia is currently undergoing critical maintenance in Mystic, Connecticut. Her participation in this year’s race helps support the schooner’s preservation, educational programs, and upcoming participation in Sail250, a national maritime celebration in 2026.
Denis Sullivan supporting World Ocean School/Alexandria Seaport Foundation - $4,723.81

This is a unique and collaborative fundraiser by World Ocean School (WOS) and Alexandria Seaport Foundation (ASF) to cover the costs for up to 18 ASF current and graduate Apprentices to sail in the 2025 Great Chesapeake Bay Schooner Race aboard the Schooner Denis Sullivan for a an educational trip of a lifetime.
Schooner Denis Sullivan: is a three-masted wooden gaff rigged schooner originally from Milwaukee. The only existing replica of a 19th century Great Lakes schooner, she was envisioned and built by a Milwaukee-based team of professionals and volunteers.
World Ocean School: We empower students from all backgrounds to be courageous and compassionate changemakers for themselves, their communities, and our planet through transformative education aboard our iconic tall ships. World Ocean School provides immersive, hands-on education to more than 600 students from diverse backgrounds each year. Since our founding in 2002, more than 23,000 students have participated in our progams.
Alexandria Seaport Foundation: The Apprentice Program is designed for young adults aged 18-23 who are eager to find a new path. We use the crafts of woodworking and traditional boatbuilding to teach job skills and positive habits that our apprentices need for success in both their work and personal life. Apprentices work alongside carpenters, boat builders, and volunteer mentors who teach and challenge them each day.
Woodwind supporting GCBSR Education Program - $2,999.44
![]()
Schooner Woodwind was built to make sailing dreams come true back in 1993 by the Kaye family. For the past 30+ years, guests from all over the world have sailed on her and her sistership, Woodwind II, for public cruises, private events, multi-day cruises and educational cruises. Woodwind II is the “movie star” of the family – she played an important role in the movie Wedding Crashers. But it’s the classic Woodwind that sails every year in the Great Chesapeake Bay Schooner Race – and she’s known to be a fast competitor!
This year Woodwind is sailing on behalf of GCBSR’s Education Fund. Contributions to the Woodwind team will be used to facilitate shipboard educational programming. Over the past years, Woodwind has used funds raised in the Virtual Race to take kids and families from the Annapolis community out sailing. Many of these kids and families would not typically have easy access to this experience. The sails are a partnership between The Great Chesapeake Bay Schooner Race, the Schooner Woodwind, and the Seafarer’s Youth Program. These programs give young people an opportunity to experience the fun of sailing and the excitement that comes with it, along with learning the science and camaraderie that sailing brings.
A.J. Meerwald supporting Bayshore Center at Bivalve - $2,903.42

The schooner A.J. Meerwald is a restored oyster dredging schooner from Bivalve, New Jersey. Launched in 1928, A.J. Meerwald embodies the true spirit of the schooner, adapted to efficiently fulfill the prevailing conditions and specific demands of her native waters. A.J. Meerwald was one of nearly five hundred schooners built along the Delaware Bay before the decline of the local shipbuilding industry in the 1930s. One hundred years later, there are only a handful of converted schooners still harvesting oysters.
Today, the A.J. Meerwald is operated by the Bayshore Center at Bivalve as a traveling classroom and vehicle to enjoy the area’s waterways. Passengers can enjoy the excitement and wonder of sailing aboard a 115-foot schooner from the age of sail. If you’re feeling adventurous, you can even join the crew in hauling lines and setting sails! Enjoy the great outdoors as you breathe in the fresh air and marvel at the scenery that surrounds you.
The Bayshore Center at Bivalve is a 501(c)(3) non-profit organization whose mission is to advance the understanding of the human impact on New Jersey’s aquatic environment through education, advocacy, and programming. BCB operates the authentically restored 1928 oyster schooner A.J. Meerwald, New Jersey’s official tall ship, as a hands-on sailing classroom throughout the region. It also operates the Delaware Bay Museum and offers shore-based programs at its campus and schooner’s home port of Bivalve on the scenic Maurice River in Cumberland County.
Luna supporting Colonial Seaport Foundation - $2,840.58

Luna is the only working replica of a colonial-era coastal trading sloop on the Chesapeake Bay. Her mission is to provide an educational and historic platform to teach visitors about the regions rich maritime history leading up to the American Revolution and serve as an environmental ambassador to help promote clean boating practices and stewardship of our natural resources.
Luna races to support the Colonial Seaport Foundation (CSF), an educational organization focused on preserving facets of America’s colonial (17th-18th century) maritime heritage by providing historically accurate information and education to the public. CSF displays and demonstrates the operation of vessel(s), equipment, tools, procedures, skills and lifestyles within the maritime community.
Farewell supporting Maryland Science Center - $2,750.79

Andy Merrill built Farewell in his backyard and launched her in 1972. Her second owner started racing the schooner in the Great Chesapeake Bay Schooner Race in 1994, and often won her class. Captain Linda Gunn purchased the schooner in 1998 after surviving cancer, and she has continued the tradition. A lover of schooners, Linda has served as Captain, Mate, and Educator aboard several different vessels. She now lives aboard Farewell and is proud to be racing on behalf of the Maryland Science Center.
Now in their 50th year and as Maryland’s largest institution dedicated to informal STEM learning, the Maryland Science Center provides valuable educational experiences both at their location in Baltimore and through outreach programming across the mid-Atlantic region. Whether they’re providing free field trip admission for every student in Maryland, offering teacher’s professional development opportunities, or expanding their outreach programs in every county, the Maryland Science Center relies on generous donors to help further their mission to inspire, empower, and engage through science education. With your help, the Maryland Science Center will be able to continue to spark excitement for STEM in the next generation, especially with underserved students.
Alliance II supporting the Watermen's Museum - $1,702.78

Schooner Alliance II offers the experience of setting sail, taking the helm and observing dolphins and osprey on the historic York River. Relive the golden age of sailing while cruising past the historic battlefield where our nation secured its independence. Schooner Alliance II departs daily, April through November, from the Riverwalk Landing Pier in Yorktown, VA. Sightseeing day cruises on the York River delve into the area’s rich history. Sunset cruises offer a romantic evening setting to conclude a day exploring the Historic Triangle. Families with children can embark on Captain Mayhem’s School of Piracy aboard the Pirate Adventure Cruise. Children participate in sailing activities, knot-tying and seamanship skills. Alliance II is a 75-foot, 2-masted, Marconi-rigged schooner.
Alliance sails to support The Waterman’s Museum. The museum focuses on the role Chesapeake Bay Watermen, from pre-colonial to modern times, played in the shaping of our nation. Historical exhibits depict military & civilian watercraft activities, crafts and methods of trade. Providing a look into the lives of the people that have worked and fought on the water. The Watermen’s Museum offers school and civic groups 11 different educational fieldtrips and conduct summer children’s programs in topics such as: archaeology, boatbuilding and environmental exploration.
Grace supporting GCBSR - $1,644.59

Grace is… not a schooner! Metaphorically speaking, think of us as a push(yawl) boat, if you will—the small but mighty craft that supports a large engineless sailing vessel. We’re behind the schooners and their mission, giving them an extra push! Grace is a Columbia 31 sloop built in Portsmouth, VA in 1966. She’s sailed thousands of miles, instrumental in creating happy memories and adventurous tales for many. For the last 12 years, we’ve been her stewards. We sail Grace to share the wonder of sailing with others, to spread kindness and understanding, to encourage learning, and to live a simple life. We’ve restored and maintained her as a reminder that beauty and functionality can go hand-in-hand, and that hands-on work is incredibly rewarding. If you’d like to learn more about our journey, visit Suzanne’s blog sailinggracefully.com.
The mission of the GCBSR is so all-encompassing and the hands at the helm so capable, this organization feels like the perfect vessel for sharing our community’s collective wealth. Schooners, in their modern-day ambassador roles, represent hard work, skill, artisanry, equality, leadership, and goodwill—what better qualities to promote? Dobbs and I see those giant sails going up, hear the young ones chanting through the work, watch them take the helm and feel the ship respond, and know that good shall continue in this world.
