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.

  • 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, MD, United States

    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, MD, United States

    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, MD, United States

    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 […]

  • RAR Brew & Irish Stew St. Day The Local Way In Cambridge

    Introducing a pop up event you won’t want to miss-our RAR BREW & IRISH STEW DRIVE THRU!!!!! RAR has sent over some of their Leprechaun Bait Out of Order cans (maybe the most popular can of the season) and we’re ready to pair it with some HOMEMADE Irish beef stew cooked up the Emily’s way!!! […]

  • Easton’s St. Patrick’s Day Parade

    106 W Dover st 106 W Dover St, easton, MD, United States

    Join Talbot Thrive for St. Patrick's Day! As St. Patrick's Day approaches, we're gearing up for an exciting celebration in Easton, and we want YOU to be a part of it! This year, we're organizing a unique and inclusive contingent for the parade - one that's vehicle-free and full of energy. Whether you're a seasoned […]

  • 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 […]

  • “Hello Spring” Annual Spring Celebration In Stevensville

    Annual Spring Celebration!! Come celebrate sunshine and flowers! We have the sweetest little free gift (with purchase) for you along with sweet treats, tasty drinks and lots of other specials. We will be donating 10% of our sales this day to our new neighbor and nonprofit, Ebeauty. Ebeauty's mission is to improve the quality of […]

  • 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 beer? Date: March, 23rd @ 1pm   Venue: 205 Grange Hall Road, Queenstown, MD, United States, Maryland 21658   Organizer: Event by Ten Eyck Brewing […]

  • 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 Queenstown Community Park on Old Wharf Lane! (Rain Date: Sunday, March 23 at 2pm) Special Guest the Easter Bunny will be present for pictures with […]