Events on Maryland’s Eastern Shore

Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.

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  • 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, the Delmarva Pride Center is presenting its Second Annual Pride Drag Show, hosted by none other than our own Eastern Shore Darling, Miranda Bryant. Bring […]

    $20 – $30
  • Fireworks Near You 2023

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

    Free
  • Plein Air Easton

    Plein Air Easton is the largest outdoor art competition in the nation and is celebrating its 19th year in 2023. Competition artists who have been juried in will descend on Easton to have their canvas' officially stamped on July 13th. Public, ticketed and free events (for the kids too) take place all week long beginning […]

  • 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
  • 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 […]

  • 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!

  • 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 time to arrive to get a seat. Play That Funky Bingo is like regular bingo but instead of calling numbers, we play parts of songs. […]

  • 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 […]

  • Chesapeake Film Festival

    Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 through 8, bringing you more fabulous films to watch anytime, anywhere. The hybrid festival begins with a LIVE weekend (Sept. 30 and Oct. 1) featuring […]

  • Easton’s Fall Kickoff 2023

    Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for a two day Fall celebration! Fall Kick Off /October First Friday Gallery Walk Giant pumpkins will decorate the downtown streets at this festive annual event. Events around town will celebrate the theme “Fall into Chesapeake!” Galleries will be open for First […]

  • Easton Fall Craft Fair 2023

    OCT. 7, 2023 -- The second annual Easton Fall Craft Fair will take place from 10am to 3pm on Saturday, Oct. 7 at Trinity Cathedral, 315 Goldsborough St. in downtown Easton.   The indoor-outdoor fair is free and will feature 35 artisans selling one-of-a-kind crafts, from jewelry and pottery to seaglass art, crocheted toys, embroidery, […]