St. Michaels Ghost Walk – Spirits of Rowdy Women
The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]
$25
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.
Events
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Wine & Unwind with Local Artists at Layton’s Chance
Wine & Unwind with Marianna Styles Sunday, July 9, 2023 from 1:00 PM to 4:00 PM EDT Sip wine, enjoy live music by Marianna Styles No fee, no reservation. Layton's Chance Vineyard & Winery Summer Concert with Uprizing Saturday, July 22, 2023 from 6:00 PM to 9:00 PM EDT Uprizing will be playing music […]
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Summer Music at Blue Ruin Cocktail Bar & Restaurant
Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm July 21st - Jayme Dingler 8-10pm July 22nd - Garrett Roe Karaoke 7-10pm July 28th - Alli Pinsky 8-10pm July 29th - Sam Pugh 7-10pm […]
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Dinner Under The Stars
Enjoy outdoor dining and music on Wednesday and Saturday evenings 5pm-10pm May 20th-September 23rd on Inner West Street in Annapolis. The streets are filled with café tables, live music and […]
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Avalon Theater Jazz Experience Aug 2nd
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! The Avalon Theatre invites you and your friends to enjoy the unofficial end […]
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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 […]
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First Fridays at Hunters Tavern
Hunters Tavern will be doing a special $5 first Friday all summer long starting June 3rd! With $5 drafts, $5 glasses of house wine, $5 flatbread, and more, your Fridays […]
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Avalon Theater Jazz Experience Aug 1st
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! Date September 1, 2023 8:00 pm - 10:00 pm Sammy Miller and the Congregation: […]
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Avalon Theater Jazz Experience Aug 3rd
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! SUN 9/3 3:00pm-6:00pm AVALON JAZZ EXPERIENCE ALLAN HARRIS: KATE’S KITCHEN The Avalon Theatre […]
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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 […]
