CHESTERTOWN, MD – Chestertown, a historic town founded in 1706, transforms into a dazzling holiday spectacle after Thanksgiving, making it a must-visit destination for those seeking festive charm reminiscent of a Hallmark movie.
The holiday season in Chestertown begins the day after Thanksgiving with the Lighting of the Town celebration. This event marks the start of the season with Santa’s grand arrival on Fountain Street, riding atop a fire truck, much to the delight of the gathered crowd. The Kent County Community Marching Band adds to the festivities with their musical performances, creating an atmosphere of joy and celebration.
The town, known for its picturesque brick sidewalks, antique stores, and cozy inns, is adorned with lights, creating a warm and inviting ambiance. Visitors can wander the streets, enjoying the holiday decorations and exploring the unique local businesses.
A highlight of Chestertown’s holiday calendar is the annual community Christmas Parade in the historic downtown. This parade, true to Hallmark movie traditions, features an array of floats, marching bands, fire trucks, and, of course, Santa Claus himself, bringing smiles to faces young and old.
The first weekend of December sees Chestertown hosting its Dickens of a Christmas celebration. This London-themed weekend is set against the backdrop of the town’s stunning architecture. The event is replete with food, shopping, carriage rides, and Victorian-style entertainment, providing an immersive holiday experience.
One of the most unique events is the “Run Like the Dickens 5K,” a themed race through the town. Participants encounter characters along the route, adding a playful and interactive element to the race.
Another significant event is the Festival of Trees Weekend, where businesses and organizations decorate Christmas trees. These trees are displayed for public viewing, creating a festive gallery of holiday spirit. The event also features appearances by Santa and Mrs. Claus and performances by various entertainment groups, ensuring that there is something for everyone to enjoy.
Chestertown’s array of holiday activities, from the Lighting of the Town to the Festival of Trees, offers a blend of tradition, community spirit, and festive cheer, making it an ideal destination for those looking to experience the magic of the holiday season.