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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.

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  • Annapolis Juneteenth Parade & Festival

    Come out and join us for our FREE 2nd annual parade and festival on Saturday, June 17, 2023! There will be TWO main stages this year, featuring headliners Avery*Sunshine, Koryn […]

    Free

  • Fireworks Near You 2023

    Add a little extra sparkle and excitement to your vacation with the local area's fireworks!  

    Free

  • 4th of July Parade & Fireworks

    Join this patriotic salute to our nation with marching bands, fire engines old and new, cars and vans, service clubs, and scouts! ROUTE: The parade kicks off at Amos Garrett and West […]

    Parking fee

  • The 78th Annual Annapolis Crab Feast

    Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis! Known as “the world’s largest crab feast,” the all-you-can-eat […]

    $90

  • Dinner Under The Stars

    Enjoy outdoor dining and music on Wednesday and Saturday evenings 5pm-10pm May 20th-September 23rd on Inner West Street in Annapolis. The streets are filled with café tables, live music and […]

  • Feasting Over Fire Series with Chesapeake Chefs

    Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your […]

  • Sea Witch Festival in Rehoboth

    Rehoboth Avenue 509 Rehoboth Beach, DE,19971, Rehoboth Beach, DE, United States

    About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown Rehoboth Beach. The Sea Witch Festival is Friday through Sunday, Oct. 27-29, 2023. Sea Witch Festival Activities All through downtown Rehoboth, and at local businesses, […]

  • Pirate & Mermaid Valentine Brunch

    About this event 2 hours Mobile eTicket $15-20 per ticket What better way to celebrate Valentine's weekend than spending it with the little ones that you love. Join us for […]

  • 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 […]