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.

  • Outdoor Pig Roast And Open Pit Chicken BBQ

    Join us for the first outdoor pig roast and open pit chicken BBQ of the season! Pulled Pork Sandwiches and all the fixings, plus that delicious fresh bbq chicken! Don't miss it! Event by Amish Country Farmers Market in Easton, MD   Amish Country Farmers Market in Easton, MD

  • 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 aged Graviera and Kefalotyri, complemented by an exquisite selection of Mediterranean olives, traditional Greek spreads. Sip and savor the complexity of Greek wines, each bottle […]

  • Kent Narrows Boat Expo

    3 Weekends to browse, tour and shop new and used boats.   The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab Deck and the Hyatt Place Kent Island.   No cost to enter and no cost to park. Crab Deck is open during the event with […]

  • Sea Glass Crab Workshop at Alibi Gastropub

    Sunday April 14 4-6pm Tickets: $46 Join us for a fun creative evening at Alibi Gastropub in Centreville to create our newest piece. We will be using paint and tumbled […]

  • Taste Of St. Michaels

    Town of St. Michaels 101 N Harbor Rd, St.Michaels, MD, United States

    Come Hungry...Leave Happy! Taste Of St. Michaels includes a tasting crawl on Saturday, April 15th from 11 am - 4 pm.   The Tasting Crawl allows participants to taste their way around St. […]

  • Tequila and Tulips

    Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila […]

  • The Eastern Shore Sea Glass and Coastal Arts Festival

    The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular festival runs 10am–5pm Saturday and 10am–4pm Sunday, with all tickets valid for admission on both days. Each ticket includes entrance to the Eastern Shore Sea […]

  • Chesapeake Bay And Maryland Eastern Shore Bike Tour

    Delight for four relaxing days in the food, history, and culture of Maryland's Chesapeake bay! You will ride along the historic Eastern Shore with the perfect mix of easy riding , gorgeous scenery, sumptuous seafood, boutique shops, and classic bayside towns from the 1600s. Explore at your own pace with our SAG wagon always nearby […]