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.
 

Summer Music at Blue Ruin Cocktail Bar & Restaurant

Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm July 21st - Jayme Dingler 8-10pm July 22nd - Garrett Roe Karaoke 7-10pm July 28th - Alli Pinsky 8-10pm July 29th - Sam Pugh 7-10pm […]

Free

Sail on the Skipjack Nathan (July 15th)

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

Saucy by the Shore Festival 2023

FELLOW SAUCE LOVERS!  Join us for a Deliciously Epic Adventure.  Taste Bud Exploding Local & National Sauce Companies! Varieties of Award-Winning Savory, Sweet, Hot, Tangy & more! FIND YOUR FLAVOR: Free Samples from Most Attending Sauce Vendors. Several Hot Sauces have been featured on the Hit YouTube series: Hot Ones! ​AWESOME LIVE MUSIC ON STAGE, […]

$20

Murder Mystery Dinner Cruise (July 15th)

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

Sail on the Skipjack Nathan (July 22nd)

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

U.S. Navy Band Cruisers Summer Outdoor Concert Series

The Avalon Summer Outdoor Concert Series is located on Harrison Street between Dover and Goldsborough Streets, begin at 7pm. They are free and open to the public. Bring some chairs and prepare to enjoy a pleasant evening of musical fun with your friends and family or call Hunters Tavern to make a dinner reservation on […]

Free

The 78th Annual Annapolis Crab Feast

Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis! Known as “the world’s largest crab feast,” the all-you-can-eat (and drink) event invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet […]

$90

The 9th Annual Sudlersville Peach Festival 23′

Friday, August 4 6PM until Fireworks Saturday, August 5 10AM – 4PM Sudlersville Peach Festival is co-hosted by the Sudlersville Volunteer Fire Company. With the best local bands providing live music, community non-profit groups serving great homemade food from pit beef to peach cobbler, local vendors offering their best hand-made crafts, and lots of great […]

Free

Dinner Under The Stars

Enjoy outdoor dining and music on Wednesday and Saturday evenings 5pm-10pm May 20th-September 23rd on Inner West Street in Annapolis. The streets are filled with café tables, live music and dancing. Reservations are encouraged.

Avalon Theater Jazz Experience Aug 2nd

Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre!   The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the soulful and swinging sounds of Jazz. This premier event will captivate music lovers and jazz enthusiasts alike and […]

Murder Mystery Dinner Cruise (August 19th)

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 […]

$85