Events on Maryland’s Eastern Shore

 
Looking for something to do in Maryland’s Eastern Shore? You’re in luck! The area is full of exciting events that are sure to delight locals and visitors alike. Whether you’re interested in food and drink festivals, live music, art exhibits, or cultural celebrations, there’s always something happening in this vibrant community.
 

2023 Spring Fling

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.

$85

Cambridge Farmers’ Market

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 […]

Free

Easton Farmers Market (May 13th)

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 […]

Free

Blackwater Refuge Wildlife Drive

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 […]

$3

Karaoke Night – The Jetty Restaurant and Dock Bar (May 17th)

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.

Free

Kent Island Farmers’ Market (May 18th)

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 […]

Free

Cambridge Classic Powerboat Regatta

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 […]

St. Michaels Farmer’s Market (20th)

  The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.

Free

39th Annual Oxford Fine Arts Fair

On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers. The exhibit featuring 36 artists from the mid-atlantic region and beyondis […]

$5

Karaoke Night – The Jetty Restaurant and Dock Bar (May 24th)

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.

Free

Classic Motor Museum Memorial Day Parade

The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up at Perry Cabin Park, and will head down Talbot St, pausing near Railroad Avenue for the emcee to announce the make, model, and driver of […]

Free

Sail on the Skipjack Nathan (May 27th)

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