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.

  • Berlin Fireworks

    Fireworks start at dusk. Bring lawn chairs, blankets and enjoy. Heron Park is open for viewing. Event Deta

    Free
  • July 4th Holiday Dinner Cruise

    Take a relaxing 3-hour cruise and dinner on one of the most exciting attractions offered on Maryland’s Eastern Shore! Followed by a beautiful display of fireworks!! The boat offers a […]

    $90
  • 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
  • 4th of July & fireworks in Cambridge

    Celebrate Independence Day on the Cambridge waterfront with fireworks over the Choptank River!  The best fireworks viewing is at Gerry Boyle Park at Great Marsh, 1 Somerset Ave. in Cambridge, […]

    Free
  • 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 Easton to have their canvas' officially stamped on July 13th. Public, ticketed and free events (for the kids too) take place all week long beginning […]

  • 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 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
  • 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: Free Samples from Most Attending Sauce Vendors. Several Hot Sauces have been featured on the Hit YouTube series: Hot Ones! ​AWESOME LIVE MUSIC ON STAGE, […]

    $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 and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local […]

    $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