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.
 

Annapolis Pride Parade & Festival

With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, […]

Free

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

Fireworks Near You 2023

Add a little extra sparkle and excitement to your vacation with the local area's fireworks!  

Free

4th of July Parade & Fireworks

Join this patriotic salute to our nation with marching bands, fire engines old and new, cars and vans, service clubs, and scouts! ROUTE: The parade kicks off at Amos Garrett and West Street. We'll head down West Street, the wrong way around Church Circle, and down Main Street. Anywhere along the parade route will provide a good view of […]

Parking fee

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

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.

Feasting Over Fire Series with Chesapeake Chefs

Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your Seat at the Table: Feasting Over Fire Dinner Series with Chesapeake Chef Service at Brampton Inn Experience a quintessential Eastern Shore tradition and join us […]

Sea Witch Festival in Rehoboth

Rehoboth Avenue 509 Rehoboth Beach, DE,19971, Rehoboth Beach, DE, United States

About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown Rehoboth Beach. The Sea Witch Festival is Friday through Sunday, Oct. 27-29, 2023. Sea Witch Festival Activities All through downtown Rehoboth, and at local businesses, […]

Pirate & Mermaid Valentine Brunch

About this event 2 hours Mobile eTicket $15-20 per ticket What better way to celebrate Valentine's weekend than spending it with the little ones that you love. Join us for a fun morning filled with great food, fun crafts, family-friendly games, and more. Date and time Saturday, February 10 · 11am - 1pm EST Location […]

2nd Annual Peake Irish Experience for Annapolis St Patrick’s Day

About this Event Get ready for our second St. Patrick's Day bar celebration with authentic Irish beverages for the biggest Irish holiday! Introducing The Peake Irish Experience, an Irish bar journey brought to you by Peake Social, Guinness, Emerald Society of Firefighters, and in partnership with Shamrock the Dock! Join us as we make our […]