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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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  • 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 […]

  • Christmas in St. Michaels at the The St. Michaels Museum

    St.Michaels Museum 201 East Chestnut Street Saint Michaels 21663, St.Michael, MD, United States

    The museum will be open free of charge during Christmas in St Michaels Weekend, December 8-10, 2023. The museum hours are Friday 1-4PM, Saturday 10AM-4PM, and Sunday 1-4PM. We are […]

  • Jingle Bells & Cocktails Ladies Night

    Aurora Vines 342 N Aurora St Easton, Easton, MD, United States

    About the eventJingle Bells & Cocktails Ladies Night! Grab the girls and join us for a fun evening! Themed Cocktails! 1/2 Priced Bottles of Wine Live Music with Anna Burgess! […]

    $20

  • Berlin New Years Eve Celebrations

    Celebrate New Years eve in Berlin with two ball drops. One for the kids at 6pm and the other at midnight. Laser shows, dancing and more. Free to attend and […]

  • Easton Carriage Tours

    VALENTINE'S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine's experience! Have a romantic carriage ride around Easton followed by dinner […]

  • Ice and Oyster Festival of Cambridge

    SCHEDULE CHANGE: Saturday, January 13th Noon-8 pm Join us for a day of Interacting with Amazing Ice Sculptures, Eating Oysters, Live Music, and Lots of Free Family Fun AT THE […]

  • Valentines’s Cookie Class Part of the Cookie Classes collection

    About this event Sunday, February 4 · 12 - 1:30pm EST 1 hour 30 minutes Mobile eTicket Valentine's Cookie Class Join us for a fun and delicious Valentine's Cookie Class at Carrie Sue’s CupCakery! Get your hands dirty and learn the art of decorating cookies with our Brandy from Shore Good Cookies. This in-person event will […]

  • 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 […]

  • Endless Vision’s Valentines Gala

    About this event 5 hours 30 minutes Mobile eTicket $50-75 per ticket come out and enjoy yourselves with some live music good vides with a prom theme and setting with a red carpet that meets you to your car with a photographer waiting to flick you up as well as proformances by Ms Ayla Dennis […]

  • 411 kitchen winter dining experience

    Join us for an unforgettable dining experience at Layton’s Chance Vineyard & Winery. Indulge in a delectable culinary journey prepared by our talented chef Chris, showcasing the finest ingredients and flavors. Immerse yourself in the cozy ambiance of the vineyard, surrounded by breathtaking views and the soothing sounds of nature. Savor each bite as you […]

  • Chesapeake Fire & Ice of Easton

    Chesapeake Fire & Ice Festival Returns to Easton, MD in 2024! Larger-than-life sculptures made of solid ice will be on display throughout the historic downtown! Festival will feature dozens of ice sculptures throughout Easton’s Historic District. Friday nights kick off will feature live ice carvings, music, and restaurant specials. The celebration will offer free live […]