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 […]

  • 20th Annual Eagle Festival

    The 20th Annual Eagle Festival at Blackwater National Wildlife Refuge on Saturday, March 16, 2024, from 9:00 a.m. to 4:00 p.m. as we celebrate birds of prey! Don’t miss out […]

  • Candle Light Cove’s Spring Festival

    Candle Light Cove 106 W Earle Ave, Easton, MD, United States

    About the eventCandle Light Cove's Spring Festival Open to the public! Free event! Community partner festival/yard sale, shop from local vendors, Easter Bunny, Food Trucks, Peep Show Voting & Winners […]

  • Cambridge Rotary Community Foundation Oyster Festival

    Join us for a shuckin' good time at the Cambridge Rotary Community Foundation Oyster Roast! Indulge in delicious oysters, mingle with fellow oyster enthusiasts, and support a great community organization. […]

  • 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 […]