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.

  • St. Michaels Ghost Walk – Spirits of Rowdy Women

    The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]

    $25
  • Sail on the Skipjack Nathan (July 8th)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]

    $40
  • Plein Air Easton

    Plein Air Easton is the largest outdoor art competition in the nation and is celebrating its 19th year in 2023. Competition artists who have been juried in will descend on […]

  • Summer Music at Blue Ruin Cocktail Bar & Restaurant

    Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm […]

    Free
  • Sail on the Skipjack Nathan (July 15th)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]

    $40
  • Saucy by the Shore Festival 2023

    FELLOW SAUCE LOVERS!  Join us for a Deliciously Epic Adventure.  Taste Bud Exploding Local & National Sauce Companies! Varieties of Award-Winning Savory, Sweet, Hot, Tangy & more! FIND YOUR FLAVOR: […]

    $20
  • Murder Mystery Dinner Cruise (July 15th)

    Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]

    $85
  • Sail on the Skipjack Nathan (July 22nd)

    Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

    $40
  • U.S. Navy Band Cruisers Summer Outdoor Concert Series

    The Avalon Summer Outdoor Concert Series is located on Harrison Street between Dover and Goldsborough Streets, begin at 7pm. They are free and open to the public. Bring some chairs and prepare to enjoy a pleasant evening of musical fun with your friends and family or call Hunters Tavern to make a dinner reservation on […]

    Free
  • 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 (and drink) event invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet […]

    $90