LEONARDTOWN, Md. — Southern Maryland’s maritime heritage was honored during the annual Blessing of the Fleet at Leonardtown Wharf, marking the start of oyster harvesting season this October with an all-day festival that honored the region’s watermen and their generations-long traditions of working in the Chesapeake Bay.
The event, organized with support from the St. Clement’s Island Museum, Watermen’s Association of St. Mary’s County, Maryland Watermen’s Association, the 7th District Optimist Club and local partners, invited the public to take part in a celebration that blended faith, history and community spirit.
The Blessing of the Fleet commemorated a centuries-old ritual of seeking divine protection and good fortune for the local fleet of boats and the families who depend on them. Watermen gathered with Pastor David Beaubien from St. Aloysius Catholic Church, local families and community members to take part in the blessing ceremony, a tradition that reflected the bond between faith and the Chesapeake Bay’s working waters.
Beaubien offered prayers over the boats and crews, asking for protection, fair weather and a safe harvest season. Holy water was sprinkled over the vessels as a symbol of faith and goodwill for all who work in the Chesapeake Bay waters.
The Blessing of the Fleet takes place annually at the St. Clement’s Island Museum site in Coltons Point, Md. However, this year the festival was held at Leonardtown Wharf because the St. Clement’s Island Museum was razed for new construction earlier this year.
Leonardtown Wharf and St. Clement’s Island share a connection through their geography and history. Each serves as a gateway to Maryland’s maritime heritage and the traditions of local watermen.
St. Clement’s Island Museum sits at Coltons Point on the Potomac River, near the site where English settlers first landed in 1634. Leonardtown Wharf, though positioned on Breton Bay, is part of the same tidal system that feeds into the Potomac. The wharf’s waters ultimately flow into the river, linking its ecosystem to the larger Chesapeake Bay watershed.
Watermen Heritage, Advocacy And Resilience
Established in 1973, the Maryland Watermen’s Association represents commercial watermen across the Chesapeake Bay region and supports environmental stewardship, legislative advocacy, safety and workforce sustainability. The association works with county-level groups including the Watermen’s Association of St. Mary’s County to coordinate community events, education and oyster restoration efforts.
Victoria Brown, treasurer with the Maryland Watermen’s Association, explained that the Blessing of the Fleet was an opportunity to raise community awareness of local watermen, who work and struggle each day of the year. She said that the Maryland waterman represents an industry minority embattled by regulation and weakened by pollution and the global industrialization of the seafood industry.
“You look at the Maryland flag, it was a farmer and a waterman. That’s who settled this whole state,” Brown said. “They were indentured servants, and you either went to the water to feed your family, or you became a sharecropper until you could buy property and become a farmer.”
The Watermen’s Association wields political influence, and Brown confirmed the organization frequently testifies in Annapolis and drives legislation to protect the interests of commercial watermen and to improve Bay health.
“We go to legislation, and we work for the whole state,” Brown said. “For all the watermen, and for the Chesapeake Bay to keep it clean and safe.”
One consequence of these actions involved a $200 million settlement in 2019 following legal action filed by Maryland counties against Exelon over alleged violations of pollution limits tied to the Conowingo Dam.
That settlement was recently succeeded by a historic $340 million settlement in October 2025 with Constellation Energy to address environmental impacts of the Conowingo Dam, and a revised state water certification plan was settled on as well. This recent action is inextricably related to the 2019 settlement, as restoration efforts weren’t meeting expectations.
Both directly impact water quality in the Susquehanna River and Chesapeake Bay and stand as a reminder of the resolve of organizations like the Maryland Watermen’s Association, the Watermen’s Association of St. Mary’s County and all the watermen who work in the Chesapeake Bay watershed.
Leonardtown Wharf: A Community Gateway
Leonardtown Wharf has been one of the town’s signature public spaces since a mid-2000s revitalization plan went into action. Overlooking Breton Bay, Leonardtown Wharf provides public water access, a boat launch, a boardwalk and green space for concerts and festivals.
It has become a central venue for many of Leonardtown’s outdoor events, drawing residents and visitors to enjoy the historic charm of downtown alongside the waterfront. According to Leonardtown Mayor Daniel Burris, the Leonardtown public space was suited perfectly to help the neighboring community of Coltons Point host the Blessing of the Fleet.
“They can’t do it at St. Clement’s Island, or over where the museum has been taken down,” Burris said. “I’m glad we could help them out here.”
Burris explained that Leonardtown Wharf is expected to see a lot of activity as Leonardtown continues to bolster it as a community hub.
The 7th District Optimist Club supported the Blessing of the Fleet with kid-friendly activities, dances, food trucks and event management. The events included three bands, dancing and evening fireworks. Dan Dozier explained that the venue was different this year because of construction, but the tradition won’t change.
“This festival started 57 years ago, and it’s tightly linked with St. Clement’s Island, where the first colonists landed in Maryland,” Dozier said. “So, normally we have the event at Coltons Point, because of that history.”
Community organizations and businesses contributed to the event, and Dozier said that is how it is funded each year — and that the event would not be possible without community sponsorship.
The 7th District Optimist Club also awarded Bobbie Tippett of St. Mary’s County the Waterman of the Year Award, recognizing Tippett’s resilience and success on the Chesapeake waterways.
Among the vendors and activities, local Viking Axe Throwing’s Kraig Eriksen had set up a two-lane axe throwing range for everyone to enjoy. He said this was his third year at Blessing of the Fleet and that the gathering offered a great opportunity to expose the community to axe throwing.
“We always do some type of kids activity — bracelets or shield decorations or wooden swords,” Eriksen said. “Then we do axes, moon bounces and stuff like that as they go.”
Local Oyster Festival Continues The Waterman Traditions
Each fall, the Blessing of the Fleet carries its heritage through to the U.S. Oyster Festival, one of Southern Maryland’s signature tourism events. The festival celebrates the region’s working watermen and the heritage of oyster harvesting that has shaped St. Mary’s County for centuries.
Held at the St. Mary’s County Fairgrounds in Leonardtown, the 59th Annual U.S. Oyster Festival takes place Oct. 18 and 19. The event draws thousands of visitors who come to enjoy local seafood, live music, artisan vendors and the famous national oyster shucking competition. Contestants from across the country compete for the title of U.S. National Champion and the chance to represent America at the World Oyster Opening Championships in Galway, Ireland.
For many, including the local watermen associations, the Oyster Festival is a continuation of the same traditions honored by the Blessing of the Fleet — a celebration of watermen, faith and the bounty of the Chesapeake Bay.
“The Watermen’s Association of St. Mary’s County started the Oyster Festival,” Victoria Brown said. “At the first Oyster Festival, it was St. Mary’s County watermen that started it, and then it got so big that they got the Rotary Club involved in it, and that’s how it’s grown.”
The Oyster Festival reinforces Leonardtown’s role as a Southern Maryland tourism hub — where heritage, community and local flavor meet.
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