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.
 

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

St. Michaels Farmer’s Market

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 […]

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 […]

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

Crab Feast Cruise

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, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local seafood and Eastern […]

$75

Cambridge Farmers’ Market

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 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 […]

Free

Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)

Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

$65

St. Michaels Yacht Beer Tasting Cruise

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 […]

$115

St. Michaels Yacht Wine Tasting Cruise

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 […]

$115

Chesapeake Bay Champagne Sunset Sail

Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St […]

$115