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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  • 39th Annual Oxford Fine Arts Fair

    On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers. The exhibit featuring 36 artists from the mid-atlantic region and beyondis […]

    $5
  • Fireworks Near You 2023

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

    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 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 […]

  • 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 […]

  • Oktoberfest in Berlin

    Berlin Oktoberfest & Sidewalk Sale 2 Bands! Authentic Oktoberfest music featuring The Edelweiss Band! Plus local favorite The Dunehounds perform sponsored by The Sterling Tavern Cascading Carlos Juggling Shows – Scales […]

  • 38th Annual Festival of Trees

    “Caroling, Caroling Through the Town” is the theme for the 2023 Festival of Trees which will be held in The Gold Room of The Tidewater Inn from Saturday, November 25 […]