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.
 

  • 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
  • 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 just got much better!

  • 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 […]

  • 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 […]

  • 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 […]

  • Artisans on the Choptank

    Artisan Market featuring local artisans! We will have a DIY craft, flower bar, craft beer, food and music! No cost to attend! Rain or shine- we will set up outside weather permitting. This is two events in 2023!   September 16: 11am-3pm   December 2nd: 4pm-10pm

  • The Maryland Wine Festival of Carroll County

    Carroll County’s 39th Maryland Wine Celebration! An Outdoor Event Featuring Wine, Live Music, and Local Vendors. Explorer Pass | $65* Enjoy an upgraded Maryland Wine Festival experience. The Explorer Pass includes admission to the Main Field, the Maryland Wine Explorer Village and includes: • Exclusive, curated Maryland-grown wine samples • Admission to an exclusive seating […]

    $65