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.
The 4-mile long Wildlife Drive is open from sunrise to sunset every day, takes you through several types of wildlife-rich habitat found at Blackwater National Wildlife Refuge. Wildlife Drive is paved, and can be accessed by vehicle, bicycle, or foot. An entrance fee is required for the Drive, and can be paid at the […]
The market with a U-Pick strawberry, blackberry, blueberry and cherry patch, U-Cut flower patch, and a beautiful selection of hanging baskets, perennials, annuals, and planters straight from their own greenhouse. […]
Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm) With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses: Glasses of […]
Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.
Once the oldest working courthouse in Maryland now currently the Old Courthouse Distilling was established in 2019! Distillery Hours Wednesday - 3:00pm to 9:00pm Thursday - 3:00pm to 9:00pm Friday […]
The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers […]
Take a relaxing 3-hour cruise 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, […]
Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite! What’s better than a waterfront Farmer’s Market? The market […]
Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail […]
Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in […]
From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly […]
With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. Experience local selection of seasonal fruits and vegetables. Hand crafted jewelry, crafts, home decor and more! Homemade baked goods, beauty products, local breweries and restaurants […]
Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays. Live music starts at 10am. Free to attend, free to park! Farms: Bennett Orchards: Peaches and Blueberries (in season only) BayBees Farm: Honey Assateague Farm: Flowers Bratten […]
One of the largest classic boat shows in the Mid-Atlantic region. On Father’s Day weekend! Featuring the theme, “Your First Love,” members of the Antique & Classic Boat Society-Chesapeake Bay Chapter will show approximately 100 antique and classic cruisers, runabouts and racers in water and on land. Other attractions include educational seminars, maritime vendors, juried […]
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 […]
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 […]
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 […]
