Here Are the Best Eastern Shore, MD, Christmas Events

From dazzling boat parades to eclectic Christmas tree lightings, Eastern Shore, MD, Christmas events are not to be missed. This holiday season, take a break from the hectic pace of everyday life with an escape to the picturesque, small town of Rock Hall, Maryland.

When you’re planning your trip to attend Eastern Shore, MD, Christmas events, be sure to utilize our Chesapeake Bay Vacation Guide. It outlines all of the area’s best restaurants, historical sites, outdoor activities, events, and more! Plus, it’s free to use. 

Take a Look at the Vacation Guide 

All About the Best Eastern Shore, MD, Christmas Events

Lighted Boat Parade

lighted christmas boat parade on water

Are you searching for a new and exciting way to get into the holiday spirit? Visit Rock Hall and celebrate the holiday season at the annual Lighted Boat Parade. This extravaganza showcases a magical display of beautifully decorated boats cruising through the Rock Hall Harbor. Whether you’re a local or visitor, this enchanting event is one of the best ways to welcome the most wonderful time of year! Be sure to keep your eyes peeled for a jolly man with a white beard—Santa Claus will be making an appearance on one of the boats! 

Annual Christmas Celebration on Main Street

Following the arrival of Santa via boat, he’ll climb aboard a fire truck and proceed to Main Street in Rock Hall for a festive, family-friendly Christmas celebration. Your ears will be filled with joy and Christmas cheer as carolers sing holiday tunes. There will also be a big fire pit in Main Street where you can gather to roast marshmallows and sip hot chocolate

Community Crab Basket Christmas Tree Lighting

Each year on the first Saturday of December, friends and family from all over are invited to Rock Hall, MD, to attend the Community Crab Basket Christmas Tree Lighting. This spectacular and unique tree is featured in the center of Main Street. This tree reflects the culture and tradition of the Maryland Eastern Shore, as it is wholly made up of hand-painted crab baskets, also known as crab pots. However, these baskets are particularly special and sentimental. Each one is decorated and dedicated to the memory of a loved one that has passed away. This event is a perfect example of love bringing people together during the holiday season. To learn more about the Crab Basket Tree or to order a painted basket for the tree, visit the event website

Rock Hall Feast of the 7 Fishes

Here in Kent County on the Maryland Eastern Shore, we take pride in our local seafood and our fisherman culture. This Christmas season, we want to celebrate that. During the second weekend of December, head to Rock Hall to check out the exciting Feast of the 7 Fishes. Almost all of Rock Hall’s restaurants will be participating in this one of a kind celebration. Each restaurant will feature a seafood dinner, including an appetizer, entree, and dessert, all for an exclusive price. There’s no better way to celebrate the holiday and eat like a local. 

A Dickens of a Christmas

Just 20 minutes away from Inn at Huntingfield Creek, is the charming town of Chestertown, MD. Each year, they ring in the holiday season with their annual “A Dickens of a Christmas.” The historic town will transform into Dickens-era celebration complete with carriage rides, street theater, live music, food vendors, a historic house tour, and more!

Stay at the Luxurious Inn at Huntingfield Creek

Woods Cottage Fireplace

During your trip to explore Eastern Shore, MD, Christmas events, make yourself at home at Inn at Huntingfield Creek. We take extra pride in our gorgeous inn around the holiday season, as we adorn it with twinkling holiday lights and Christmas trees. You’ll be mesmerized by our one of a kind Sugar Plum Tree…you’ll have to see it to believe it! 

During your stay at Inn at Huntingfield Creek, rest your head in one of our serene cottages, such as our Woods Cottage. Woods Cottage features warm, rich tones complemented by lush color accents and woodland themed accessories. Its upscale amenities include a Tempur-Pedic king-size bed, fine linens and bedding, monogrammed spa robes, a luxurious soaking tub, and rain-shower. When you stay in this cottage, you’ll enjoy spectacular field views, sunset vistas, and a peek at the waterfront from your private deck. The holiday season will be here before you know it. Check our availability and start planning your trip today! 

Spread Holiday Cheer on the Maryland Eastern Shore