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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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  • Schellville’s Beer and Wine Fest

    Tanger Outlets Seaside 36470 Seaside Outlet Drive Rehoboth Beach, DE 19971, Rehoboth Beach, DE, United States

    About this event 🍻🍷 Get ready to raise your glasses at Schellville's Beer and Wine Fest- Wicked Brew Bash! 🍻🍷   Join us for a delightful celebration of craft beers […]

    $40

  • Waterfowl Festival

    More than 1,000 volunteers work year-round to stage the show, most coming back to lend their talents and time year after year. Art collectors find exceptional wildlife art from renowned […]

  • Ice Ice Berlin and Tree Lighting

    Join us as we begin the holiday season featuring beautifully carved Ice Sculptures sponsored by the Berlin businesses! 30+ Holiday themed lighted sculptures Tree is lit at 6pm Greet Santa […]

  • 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 […]

  • Cambridge Ice & Oyster Fest 2024

    Winter, Wildlife & Water Ways Welcome winter with the Eastern Shore's Ice & Oyster Fest. The event features dozens of dazzling ice sculptures, interactive games for children of all ages, […]

  • 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

  • Elf the Musical

    Avalon Theaters 40 E Dover St Ste 200, Easton, MD, United States

    Performance Schedule: Thursday, December 7 – Doors: 6:30pm; Show: 7:00pm – GREEN CAST Friday, December 8 – Doors: 6:30pm; Show: 7:00pm – RED CAST Saturday, December 9 – Doors: 6:30pm; […]

    $30

  • 37th Annual Christmas In St. Michaels

    Christmas in St. Michaels ∴ A Weekend Celebrating Joy! ∴ Christmas in St. Michaels will be held December 8-10, 2023.  We look forward to welcoming you all to our festive […]

  • Talbot Street Parade

    Town of St. Michaels 101 N Harbor Rd, St.Michaels, MD, United States

    Date: December 9, 2023 Time: 10:30 AM - 12:00 PM EST Website:https://christmasinstmichaels.org/product/talbot-street-parade/ Event Description: Who doesn’t love a traditional Christmas parade complete with marching bands, antique cars and boats, fire […]

  • 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 […]