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.

Looking for events near your rental? Browse vacation rentals by town.

  • OysterFest

    Get ready to sip, slurp, and savor at the Chesapeake Bay’s favorite fall festival!  The event features live music on two stages, boat rides, retriever demonstrations, oysters, and more.

    Free
  • 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 and exquisite wines from the finest local and regional breweries and wineries while listening to Hot Sauce from 6-8pm. Mark your calendars for October 28th […]

    $40
  • 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 at Kringle Kottage at the Taylor House Museum Music by DJ Big Al Reno  – Shops open late!

  • 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 to Tuesday, November 28, 2023. In a magical holiday setting, fifty beautifully decorated trees sponsored by individuals and businesses will be on display. In addition, […]

  • 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 excited to share a special display of miniature rooms created by Jo Storey, our Docent Coordinator. The display of miniature rooms shows what a home […]

  • 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 events throughout the weekend.  Click the Events tab above to see all that we have planned.   Look forward to purchasing your favorite ornament – […]

  • 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 engines, horses, kazoo bands and llamas?! Perhaps you may even see a penny farthing.  Santa and Mrs. Claus will arrive to close out the parade. […]

  • Cars and Coffee in the Barn Classic Motor Museum Saturdays

    Motor Museum 102 E. Marengo Street, St. Michaels, MD, United States

    Hosted by: Classic Motor Museum St Michaels Where: 102 E. Marengo Street, St. Michaels Maryland. When: Every Saturday Morning  9 am to 11 am. From now through the end of March we have a "Coffee in the Barn" event every Saturday. This happens directly in the museum barn. It is free for members and $5 for non-members. It […]

  • Build-Your-Own Bloody Mary/Maria Bar at The Fool’s Lantern

    The Fool's Lantern 310 S. Talbot St., St.Michaels, MD, United States

    Join us every Saturday and Sunday at The Fool's Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made mix, and then choose from over 20 toppings to create your unique drink. Pair it with items from our brunch menu to start your weekends […]

  • 6th Annual St. Michaels ChocolateFest

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

    St. Michaels ChocolateFest will be held March 2, 2024 and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts.  The Chocolate Crawl will take place on Saturday, March 2, 2024 from 11:00 a.m. - 4:00 p.m. until sold out throughout the Town of St. Michaels at participating businesses […]

  • Simpatico Free Wine Tasting Events Every Weekend

    Simpatico 104-106 Railroad Ave, St.Michaels, MD, United States

    top by Simpatico's Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and chat with our enthusiastic staff - We Love All Things Italian!  We also offer free tastings all week long.  Salute!

  • Awww Shucks Oyster Harvest In Queenstown

    They will be shucking oysters all day long! More details as we get closer to the day. What pairs better with a briny, sweet oyster than an ice cold fresh beer? Date: March, 23rd @ 1pm   Venue: 205 Grange Hall Road, Queenstown, MD, United States, Maryland 21658   Organizer: Event by Ten Eyck Brewing […]