There’s no better way to experience the heart and heritage of Maryland’s Eastern Shore than at Watermen’s Appreciation Day at the Chesapeake Bay Maritime Museum in St. Michaels.
On Sunday, August 9, from 10 AM–4 PM, this beloved annual tradition celebrates the hardworking watermen who have shaped the Chesapeake Bay community for generations. Hosted in partnership with the Talbot Watermen Association, the event brings together locals and visitors for a day filled with seafood, music, family fun, and waterfront traditions.
One of the biggest highlights of the day is the Watermen’s Rodeo, where the Chesapeake Cowboys showcase their skills in a thrilling workboat docking competition along the Miles River waterfront. Guests can cheer on these talented captains as they maneuver traditional deadrise boats in a timed challenge.
Of course, no Eastern Shore celebration would be complete without steamed crabs! Beginning at 11 AM, guests can enjoy fresh steamed crabs served by local watermen, along with other local favorites and food truck specialties.
The day also features live music, arts and crafts vendors, a silent auction benefiting the Talbot Watermen Association, and plenty of activities for the whole family — including children’s games, inflatables, face painting, and hands-on experiences that showcase the life and traditions of Chesapeake watermen.
Visitors are also encouraged to explore the Chesapeake Bay Maritime Museum’s waterfront campus, including exhibits that share the stories, tools, and traditions of the people who have called the Bay home for generations.
Watermen’s Appreciation Day is more than just an event — it’s a celebration of the culture, community, and connection that make Maryland’s Eastern Shore such a special place.
Watermen’s Appreciation Day
Chesapeake Bay Maritime Museum | St. Michaels, Maryland
Sunday, August 9
10 AM–4 PM
Whether you’re enjoying a dozen crabs by the water, watching the workboats race, or simply soaking in the Chesapeake views, this is one Eastern Shore tradition you won’t want to miss.
