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.

  • Easton Farmers Market

    From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly […]

    Free
  • 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 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 […]

  • 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!   Also check out other Music Events in Easton, Entertainment Events in Easton.

    $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; Show: 7:00pm – GREEN CAST Sunday, December 10, Matinee – Doors: 1:30pm; Show: 2:00pm – RED CAST Thursday, December 14 – Doors: 6:30pm; Show: 7:00pm […]

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

  • 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 park.

  • 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 EVENT     See dazzling ice sculptures showcasing Eastern Shore culture, wildlife & more! Entertain your family with kid-friendly golf, thrones, ice slide, and other […]

  • 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 […]