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.
 

The Berlin Farmers Market

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 […]

Free

Waterfront Wine & Jazz Dinner

  Guest( 10 per table) will be greeted with a choice of our sparkling Rosés, Slipstream or Moondance(new), while you settle in, laugh with friends, and feel your entire self begin to relax as you soak in the views accompanied by the melodies of our jazz trio. Part of the before dinner experience will include wine […]

$175

Delmarva Pride Festival

Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.

Delmarva Pride Presents 2nd Annual Drag Show

If you attended last year’s event, you know this show is going to be a wonderful night of entertainment fit for a queen! As part of its Annual Pride Weekend, […]

$20 – $30

Annapolis Juneteenth Parade & Festival

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 Hawthorne, Pastor Mike Jr., Beverly Crawford, the Chuck Brown Band, and a host of local talent! Fireworks will immediately follow the show! PARADE- SATURDAY, JUNE […]

Free

Sail on the Skipjack Nathan (June 17th)

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

Murder Mystery Dinner Cruise (June 17th)

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 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 […]

$85

Father’s Day Riverboat 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 […]

$80

St. Michaels Ghost Walk – Spirits of Rowdy Women

The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]

$25

Sail on the Skipjack Nathan (July 1st)

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

Special 4th of July Fireworks Cruise

Saturday July 2, 2022 8 PM to 10 PM, $150 per person plus tax and gratuity. Join us for the ultimate Independence Day celebration and Sail Selina the Ultimate St […]

$150