5 Magical Ways to Celebrate Christmas on Maryland’s Eastern Shore

Get in the spirit with a visit to one of the Mid-Atlantic’s most charming holiday destinations. We’ve put together a list of the five most magical ways to celebrate Christmas on Maryland’s Eastern Shore, that way you can spend less time planning and more time taking in everything the season has to offer. Enjoy beautiful decorations, live performances, gift shopping, and so much more!

guitar at Christmas

1. Catch a Festive Show

Immerse yourself in a classical literary tradition with Dickens of a Christmas, Chestertown’s annual holiday festival inspired by “A Christmas Carol” by Charles Dickens. There will be live music, street performances, food and refreshments from local vendors, and carriage rides! It is held in the Chestertown historic district, a beautiful part of the city with lots to see and do in addition to the festival, and we highly recommend having a look around when you get the chance.

audience of musical at Christmas in Maryland

2. Enjoy a Musical

Take a break from the holiday rush with a show at the Garfield Center for the Arts. “Shrek: The Musical” is running each weekend in December and has been lovingly adapted into a stage musical with fun for the whole family. Make sure and book your tickets as soon as possible as there are a limited number of performances available.

two friends drinking hot chocolate at a Maryland Christmas event

3. Attend Rock Hall Hometown Christmas

Take a stroll through downtown at Rock Hall Hometown Christmas, only a short 20-minute drive away from Chestertown. Soak in the festive atmosphere and explore local shops hosting mini-events, beautifully decorated open houses, or even go on a scenic carriage ride! Mark your calendars and check out all there is to do Rock Hall.

shopping for wreaths at a christmas event in maryland

4. Visit the Open Air Yuletide Festival & Holiday Marketplace

Attend an event at the historic Mount Harmon Plantation with their yearly Open Air Yuletide Festival & Holiday Marketplace! The grounds of the beautifully restored plantation are adorned in timeless seasonal decor all throughout and it makes shopping at the open-air artisan marketplace a real treat. See the walled boxwood garden, grand manor house, and more on a self-guided walking tour and learn more about the plantation’s past. The highlight of the festival, the holiday decorations & greens sale, features artfully crafted decorations made using greens grown on plantation grounds and proudly sponsored by the Greenfingers Garden Club. The celebration is a highly recommended visit for new and returning guests alike.

Christmas decorations at Brampton Inn, a Maryland B&B

5. Celebrate at Brampton Inn

Experience all these local events and more with a stay at Brampton Inn, a charming Chestertown MD Bed and Breakfast with everything you need for a comfy seasonal getaway. The B&B is decked out in cheer with decorations and a warm atmosphere, perfect for frosty winter nights. Warm-up with a glass of wine by the fireplace after a long day out on the town and relax in one of our private and spacious rooms. Get cozy in one of our cottages away from the property in a romantic and secluded wooded area, or enjoy a stay in the historic manor house with luxurious amenities like jetted hot tubs and more. In addition, we will also be hosting a delicious Christmas dinner that you won’t want to miss, so make sure you book your slot ahead of time and we will notify guests of more details when they are available. Plan ahead for upcoming Christmas events on Maryland’s Eastern Shore and have a memorable holiday season in Chestertown.

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Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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