The holiday season on Maryland’s Eastern Shore is like stepping into a storybook. From twinkling lighted parades to historic downtown celebrations, every town brings its own charm to the season. Whether you’re a longtime local or visiting for the first time, this guide will help you make the most of the most wonderful time of the year.
Bookmark this post— it’s your evergreen holiday resource, updated annually with the latest festive events!
Annual Holiday Events by Town
Centreville, Maryland Holiday Events:
- Centreville Christmas Parade: Each year the town of Centreville celebrates the holiday season with their annual Christmas Parade!
Chestertown, Maryland Holiday Events:
- Dickens of a Christmas: Step back into 1840s London and experience the holiday season as Charles Dickens imaged it the first weekend of December! This annual event includes live music, local artisan vendors, and children’s activities including Santa visits.
Easton, Maryland Holiday Events:
- Festival of Trees: A dazzling display of decorated trees benefiting Talbot Hospice. Held at The Tidewater Inn — magical for all ages!
- Easton Holiday Parade: Kicks off the season with marching bands, floats, and Santa Claus himself.
Grasonville, Maryland Holiday Events:
- Kent Narrows Crab Basket Tree Lighting: This annual event is held by the Queen Anne’s County Watermen’s Association at the Fisherman’s Crab Deck. The day is filled with a vendor fiar with local artisans, food trucks, and kids activities along with photos with Santa! The main tree lighting ceremony begins in the evening usually around 6PM.
Rock Hall, Maryland Holiday Events:
- Santa’s Arrival & Tree Lighting: At this annual event, Santa arrives by boat to light the tree made of decorated crab baskets that honor loved ones. There is a boat parade and the event typically features s’mores by a fire pit and visits with Santa!
- New Year’s Eve Rockfish Drop: The town of Rock Hall annually celebrates with a rockfish drop from a tower truck along with other children’s activities.
St. Michaels, Maryland Holiday Events:
- Midnight Madness: Held the first Saturday in December, this beloved event features local shops open late, special sales, prize drawings, and live holiday music all evening. A magical night of shopping and strolling through town.
- Lighted Boat Parade: Watch beautifully decorated boats light up the harbor — an unforgettable sight.
Stevensville, Maryland Holiday Events:
- IllumINNation: An annual holiday light display at The Inn at Chesapeake Bay Beach Club that occurs every December. The event features thousands of twinkling lights in the gardens along with a large walk-through ornament display. There is a daily lighting ceremony at 5:15PM and is open to hotel guests and locals visiting the on-site restaurants, spa, or market.
Festive Activities for All Ages
Beyond parades and festivals, the Eastern Shore offers plenty of cozy holiday activities:
- Holiday Markets & Pop-Ups: Find handcrafted gifts, baked goods, and local art.
- Tree Lighting Ceremonies: Most towns host a community tree lighting in early December.
- Carriage Rides (when available): A charming way to take in decorated streets.
- Historic Home Tours: Some towns offer seasonal tours of homes decorated in holiday style.
Thinking About a Move to the Shore?
Whether you’re visiting, returning home for the holidays, or considering a move to the Eastern Shore, these events are a great way to experience the close-knit community spirit that makes this place so special.
The holidays are the perfect time to get to know the area! If you’re exploring neighborhoods or just curious about what life on the Shore looks like year-round, let’s connect. I’d love to help you find your perfect fit here on Maryland’s Eastern Shore.
Contact me today to learn more about available homes and community insights!
