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 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 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

First Fridays at Hunters Tavern

Hunters Tavern will be doing a special $5 first Friday all summer long starting June 3rd! With $5 drafts, $5 glasses of house wine, $5 flatbread, and more, your Fridays […]

Avalon Theater Jazz Experience Aug 1st

Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! Date September 1, 2023 8:00 pm - 10:00 pm Sammy Miller and the Congregation: The Music of 1973   The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the […]

Avalon Theater Jazz Experience Aug 3rd

Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! SUN 9/3 3:00pm-6:00pm AVALON JAZZ EXPERIENCE ALLAN HARRIS: KATE’S KITCHEN   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 […]

Easton Music Bingo at Doc’s Downtown Grille

MUSIC BINGO - Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best […]

Light Night at Cambridge Yacht Club

The annual LIGHT NIGHT is Saturday, September 9, 2023, at the Cambridge Yacht Club. A celebration of the Choptank River Lighthouse and the difference “The Jewel of the Choptank” is making for our community, the event will feature heavy appetizers, fun auctions, a “wine wall,” dancing, and much more. Outdoor tented space available in addition […]

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 […]

IRONMAN MARYLAND

At IRONMAN Maryland, part of the VinFast IRONMAN North America Series, race day does not make us individuals that are competing against ourselves. When we toe the line, we become a team of athletes that join forces to overcome whatever challenges race day brings. We are allies that stick by each other and offer words of encouragement. And […]