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 […]

  • Annual Multicultural Festival in Easton

    Save the date! The Avalon Foundation’s Annual Multicultural Festival returns to Easton’s Idlewild Park with a fun day of diverse musical traditions, arts, and food on Saturday, May 4, 2024, […]

  • Sip | Savor | Shop

    Immerse yourself in the enchanting flavors and cultural richness of Greece at our monthly Greek food experience! Discover an enticing assortment of cheeses, ranging from creamy feta and Manouri, to […]

  • First Ever Plant Swap in Centreville

    • Bring in any indoor/outdoor plants, seeds, plant/garden books, tools and take something fun and new home! • Please make sure that all items are clean and pest free. • […]

  • May Day Flower Celebration

    Join us in downtown Easton, MD for a spring celebration! Easton will be decked out in flowers, bows, and bouquets for a lovely spring celebration. Merchants will be competing for […]

  • Jazz on the Miles River in Saint Michaels

    Sip cocktails and enjoy the sounds of JG and the Initials aboard PATRIOT while floating on the gentle waters of the Miles River on a 90-minute cruise. In the early […]

  • Bull Roast at Grasonville’s VFW

    Food, Corn-hole, and much more start at 3 the fabulous Kick Back Band will start playing around 6 Tickets are available for Purchase at the VFW 410-827-8194   Venue: Grasonville […]

  • JCT 33 on the Patio at Corah’s Corner

    Join us on Saturday, May 4th for JCT 33 on the patio! 6-9pm Live & Local! Let’s kick off our Music Season the proper way! Come JOIN us for some […]

  • Berries and Booze in Frankford

    Calling all strawberry lovers!!! Join us for a day of berries and booze! Fresh strawberries, strawberry treats and baked goods! Strawberry slushies!! The best!!! Over 40 local boutiques and vendors! […]

  • Springtime in Paris Concert

    Oh-la-la! Our spring concert is a whimsical treat for your ears. Go to our website at www.capitalringers.org for info on all dates and venues. A free will offering will be […]