Sail on the Skipjack Nathan (July 15th)
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]
$40
12 events found.
Events on Maryland’s Eastern Shore
Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.
Looking for events near your rental? Browse vacation rentals by town.
Dorchester County
Events
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Murder Mystery Dinner Cruise (July 15th)
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]
$85 -
Sail on the Skipjack Nathan (July 22nd)
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]
$40 -
Thunder on the Choptank Boat Races
Thunder on the Choptank Boat Races at Gerry Boyle Park at Great Marsh.
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Murder Mystery Dinner Cruise (August 19th)
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]
$85 -
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Easton Music Bingo at Doc’s Downtown Grille
MUSIC BINGO - Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best […]
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Light Night at Cambridge Yacht Club
The annual LIGHT NIGHT is Saturday, September 9, 2023, at the Cambridge Yacht Club. A celebration of the Choptank River Lighthouse and the difference “The Jewel of the Choptank” is […]
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Feasting Over Fire Series with Chesapeake Chefs
Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your Seat at the Table: Feasting Over Fire Dinner Series with Chesapeake Chef Service at Brampton Inn Experience a quintessential Eastern Shore tradition and join us […]
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IRONMAN MARYLAND
At IRONMAN Maryland, part of the VinFast IRONMAN North America Series, race day does not make us individuals that are competing against ourselves. When we toe the line, we become a team of […]
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Wine Down at Laytons Chance Winery
It's that time of year!!! Zeta Phi Beta Sorority, Incorporated, Iota Chi Zeta Chapter will host it's annual "Wine Down". This fun for all event will be held on Saturday, […]
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Murder Mystery Dinner Cruise (September 16th)
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]
$85 -
Maryland Folk Festival
Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage. This large-scale multi-day outdoor event, celebrates the […]
Free
