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 a "Coffee in the Barn" event every Saturday. This happens directly in the museum barn. It is free for members and $5 for non-members. It […]

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 mix, and then choose from over 20 toppings to create your unique drink. Pair it with items from our brunch menu to start your weekends […]

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 chat with our enthusiastic staff - We Love All Things Italian!  We also offer free tastings all week long.  Salute!

Adult Easter Egg Hunt 2024

Join in the fun at Layton's Chance! This adult only Easter Egg hunt is a twist on the traditional hunt! At 6:00pm blindfolded teams of 2 will compete during fun and goofy ways to find hidden eggs. Entertainment, prizes, and of course lots of laughs will fill this evening! After the hunt there will be […]

3rd Annual Glow In The Dark Easter egg hunt At The Queenstown’s Moose Lodge

Friday night, March 22nd for our 3rd Annual Moose Glow in the Dark Easter Egg Hunt! There's nothing else that will make you feel like a kid again then hunting Glow in the dark eggs filled with treats!!   $15/person to participate, you'll find eggs filled with scratch offs, liquor minis, moose bucks, drink chips […]