St. Michaels is getting ready for a Sunday showdown on the Miles River, where working boats, steamed crabs and Eastern Shore traditions will take over the waterfront. Watermen’s Appreciation Day returns next Sunday from 10 a.m. to 4 p.m. at the Chesapeake Bay Maritime Museum.
The annual celebration is organized with the Talbot Watermen Association and honors the men and women who make their living on the Chesapeake Bay. According to CBMM’s 2026 event listing, the festival will combine a workboat docking contest with live music, local food, children’s activities, vendors and a silent auction benefiting the association.
The Chesapeake Cowboys Take Over The Miles River
The day’s main spectacle begins at noon, when the Chesapeake Cowboys maneuver deadrise workboats into assigned slips during a timed docking competition. As reported by Eye On Annapolis, spectators can watch from bleachers, the Hooper Strait Lighthouse or a livestream inside the Van Lennep Auditorium.
Crab service starts at 11 a.m., with steamed crabs priced at $25 per dozen and served with an ear of corn, according to CBMM’s event details. Bird Dog and the Road Kings will provide live music, while children can join crab races, baiting contests, inflatables, face painting and other hands-on activities. Visitors can also browse waterfront exhibits and take a narrated Patriot Cruise on the Miles River.
Tickets Cost More At The Door
Advance admission is $22 for adults, $19 for seniors and students, $10 for active and retired military members, and $9 for children ages 6 through 17; children 5 and younger get in free. Eye On Annapolis’ preview notes that tickets purchased at the door cost $2 more in each paid category.
Licensed watermen and their immediate families receive free admission with an active license. Free overflow parking and shuttle service will be available at St. Michaels Middle/High School, giving visitors a way around what could be a very crowded museum lot.
