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
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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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 making for our community, the event will feature heavy appetizers, fun auctions, a “wine wall,” dancing, and much more. Outdoor tented space available in addition […]
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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 athletes that join forces to overcome whatever challenges race day brings. We are allies that stick by each other and offer words of encouragement. And […]
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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, September 16, 2023 at Layton's Chance Vineyard from 4:30-8:00 pm. Tickets are $45 (until July 1st) which includes wine tasting, food, and entertainment. After July […]
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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 and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local […]
$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 roots, richness and variety of American culture. It features hundreds of the nation’s finest musicians, dancers, craftspeople and other keepers of culture in performances, workshops, […]
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Oktoberfest in Berlin
Berlin Oktoberfest & Sidewalk Sale 2 Bands! Authentic Oktoberfest music featuring The Edelweiss Band! Plus local favorite The Dunehounds perform sponsored by The Sterling Tavern Cascading Carlos Juggling Shows – Scales n Tales Animal Show Plus the Fall Sidewalk Sale! MORE Beer stations this year and featuring a variety of OCTOBERFEST beer too! German food featuring […]
