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.

Ongoing

Easton Carriage Tours

VALENTINE'S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine's experience! Have a romantic carriage ride around Easton followed by dinner […]

Cars and Coffee in the Barn Classic Motor Museum Saturdays

Motor Museum 102 E. Marengo Street, St. Michaels

Hosted by: Classic Motor Museum St Michaels Where: 102 E. Marengo Street, St. Michaels Maryland. When: Every Saturday Morning  9 am to 11 am. From now through the end of March we have […]

Build-Your-Own Bloody Mary/Maria Bar at The Fool’s Lantern

The Fool's Lantern 310 S. Talbot St., St.Michaels

Join us every Saturday and Sunday at The Fool's Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made […]

Simpatico Free Wine Tasting Events Every Weekend

Simpatico 104-106 Railroad Ave, St.Michaels

top by Simpatico's Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and […]

Awww Shucks Oyster Harvest In Queenstown

They will be shucking oysters all day long! More details as we get closer to the day. What pairs better with a briny, sweet oyster than an ice cold fresh […]

Queenstown Easter Egg Hunt

Date/Time Date(s) - March 23, 2024 2:00 pm Venue Queenstown Community Park   Join us for the Queenstown Easter Egg Hunt on Saturday, March 23 at 2pm sharp at the […]