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.

  • Old School R&B Crab & Cruise in Crisfield

    Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the […]

  • The Famous Annapolis City fireworks from the Water

    Come celebrate your Independence with us. Enjoy the famous Annapolis City fireworks from the water! Public 3 hour cruise includes a tour around the harbor, sunset, and then front row […]

  • Live Music all Summer at Foxy’s Harbor Grille in St. Michaels

    Event by Foxy's Harbor Grille Venue: 125 Mulberry St, Saint Michaels, MD, United States, Maryland 21663 TODAY Groove Tide 5-8pm FRIDAY Uncle Ward 5-8pm SATURDAY Mike Miller 4-7pm SUNDAY Brandon & Thordis 4-7pm Be sure to check out our Events Tab on Foxy’s Facebook to see our Live Music Schedule for the summer! 🎶☀️ https://www.facebook.com/FoxysHarborGrille/events

  • Easton’s 4th of July Celebration Carnival

    Family Fun Carnival! On July 4th the Carnival will be open from 4-11pm and as soon as it gets dark the fireworks will light up the sky! Wristbands offered nightly!!! […]

  • Hip Hop R&B Yacht Party In Annapolis

    TICKETS AVAILABLE AT: https://hiphoprnbyachtpartyJune30.eventbrite.com Why party in the club when you can party on a yacht!!! Join us as we cruise out of Annapolis for The Hip Hop R&B Yacht […]

  • Downtown Easton’s 4th of July Sidewalk Sale

    Join our downtown retailers as they clear out their racks and make room for new inventory at the 4th of July Sidewalk Sale! This annual sale always offers BIG savings […]