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.
Taste of St. Michaels includes a Tasting Crawl on Saturday, April 15th from 11am – 4pm which allows participants to literally eat their way around the Town at award-winning restaurants. Each tasting venue will have tasting selections that feature food and drinks, Chesapeake Bay inspired. Tastings can be purchased, ranging from $1-$5, at participating venues […]
Make art together during these fun days for all ages! eARTh Arts Day Extravaganza! Saturday, April 22 10 am–1 pm FREE There is no cost to participate in Family Art Days, but please let AAM know if you are coming, as it will help them plan. Sign up online!
Let’s welcome all new beginnings for Cambridge Main Street with an evening of dinner, drinks, dancing, and a live auction. Ticket price includes 2 drink tickets. We look forward to welcoming you! Funds raised from Spring Fling go to support Cambridge Main Street operating expenses.
Operating May through November in 2023, 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 is situated in the Long Wharf park, nearby public parking. The market is within walking distance to the Municipal Marina, Skipjack Nathan, the replica Choptank River […]
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 and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts […]
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. Delicious homemade desserts are made daily. The market offers the freshest and sweetest homegrown sweet corn and tomatoes starting in late June as well as […]
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 wine are available each and every day. We also will have sangria or mulled wine occasionally, depending on the weather and our whims. Bottles: After […]
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 - 3:00pm to 9:00pm Saturday - 2:00pm to 9:00pm Blanco Rum This rum is twice distilled, then cut and charcoaled filter for a super smooth […]
Come out to the Jetty Restaurant and Dock bar for amazing food and the best drinks in the area! Enjoy the beautiful view and if you are feeling the vibes come rock the dock with Karaoke night. Every Wednesday from 6:30 – 9:30 head to the Jetty restaurant and Dock Bar for Karaoke night.
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 […]
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 20-21, 2023 on the Choptank River. About 70 boats are expected to be on hand to create an exciting two days of racing. Admission is FREE with a $5 a day charge […]
